蓝藻FBP/SBPase的制备及其与配体相互作用的分析——科研转化的化学生物学综合实验设计
作者：
冯玲玲;陈琼;李玉梦;梁景晗;王舟
期刊：
大学化学 ,2021年36(06):116-123 ISSN：1000-8438
作者机构：
华中师范大学化学学院,农药与化学生物学教育部重点实验室,武汉430079;[陈琼; 王舟; 李玉梦; 梁景晗; 冯玲玲] 华中师范大学
关键词：
化学生物学;综合实验设计;靶酶与配体相互作用;果糖-1;6-/景天庚酮糖-1;7-二磷酸酶
摘要：
以蓝藻果糖-1,6-/景天庚酮糖-1,7-二磷酸酶为靶酶,异源表达获得靶酶,分析靶酶的纯度及含量,探讨配体与靶酶的相互作用。通过本实验,学生掌握获取靶酶的方法,掌握靶酶与配体相互作用的分析方法,了解药物筛选模型建立的研究思路及实验技术,提升分析、解决问题及综合运用知识的能力,增强科研服务社会意识及责任感。
语种：
中文
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Structure-Guided Discovery of Silicon-Containing Subnanomolar Inhibitor of Hydroxyphenylpyruvate Dioxygenase as a Potential Herbicide
作者：
Qu, Ren-Yu;Nan, Jia-Xu;Yan, Yao-Chao;Chen, Qiong;Ndikuryayo, Ferdinand;...
期刊：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY ,2021年69(1):459-473 ISSN：0021-8561
通讯作者：
Lin, Hong-Yan;Yang, Guang-Fu
作者机构：
[Ndikuryayo, Ferdinand; Yang, Guang-Fu; Yang, Wen-Chao; Lin, HY; Yang, GF; Wei, Xue-Fang; Nan, Jia-Xu; Qu, Ren-Yu; Yan, Yao-Chao; Chen, Qiong; Lin, Hong-Yan] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Key Lab Pesticide & Chem Biol,Minist Educ, Wuhan 430079, Peoples R China.
通讯机构：
[Lin, HY; Yang, GF] C;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Key Lab Pesticide & Chem Biol,Minist Educ, Wuhan 430079, Peoples R China.
关键词：
quinazoline-2;4-dione;hydroxyphenylpyruvate dioxygenase;hydrophobic interaction;lead optimization;herbicide
摘要：
4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been recognized as one of the most promising targets in the field of herbicide innovation considering the severity of weed resistance currently. In a persistent effort to develop effective HPPD-inhibiting herbicides, a structure-guided strategy was carried out to perform the structural optimization for triketone-quinazoline-2,4-diones, a novel HPPD inhibitor scaffold first discovered in our lab. Herein, starting from the crystal structure of Arabidopsis thaliana (At)HPPD complexed with 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(o-tolyl)quinazoline-2,4(1H,3H)-dione (MBQ), three subseries of quinazoline-2,4-dione derivatives were designed and prepared by optimizing the hydrophobic interactions between the side chain of the core structure at the R1 position and the hydrophobic pocket at the active site entrance of AtHPPD. 6-(2-Hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(3-(trimethylsilyl)prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione (60) with the best inhibitory activity against AtHPPD was identified to be the first subnanomolar-range AtHPPD inhibitor (Ki = 0.86 nM), which significantly outperformed that of the lead compound MBQ (Ki = 8.2 nM). Further determination of the crystal structure of AtHPPD in complex with compound 60 (1.85 Å) and the binding energy calculation provided a molecular basis for the understanding of its high efficiency. Additionally, the greenhouse assay indicated that 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-propylquinazoline-2,4(1H,3H)-dione (28) and compound 60 showed acceptable crop safety against peanut and good herbicidal activity with a broad spectrum. Moreover, compound 28 also showed superior selectivity for wheat at the dosage of 120 g ai/ha and favorable herbicidal efficacy toward the gramineous weeds at the dosage of as low as 30 g ai/ha. We believe that compounds 28 and 60 have promising prospects as new herbicide candidates for wheat and peanut fields. © 2021 American Chemical Society.
语种：
英文
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Fragment-based discovery of flexible inhibitor targeting wild-type acetohydroxyacid synthase and P197L mutant
作者：
Qu, Ren-Yu;Yang, Jing-Fang;Chen, Qiong;Niu, Cong-Wei;Xi, Zhen;...
期刊：
Pest Management Science ,2020年76(10):3403-3412 ISSN：1526-498X
通讯作者：
Yang, Wen-Chao;Yang, Guang-Fu
作者机构：
[Yang, Jing-Fang; Yang, Guang-Fu; Yang, Wen-Chao; Qu, Ren-Yu; Chen, Qiong; Yang, WC; Yang, GF] Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensor Technol &, Key Lab Pesticide & Chem Biol, Coll Chem,Chem Biol Ctr,Minist Educ, Wuhan, Peoples R China.;[Xi, Zhen; Niu, Cong-Wei] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin, Peoples R China.;[Yang, Guang-Fu] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China.
通讯机构：
[Yang, WC; Yang, GF] C;Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensor Technol &, Key Lab Pesticide & Chem Biol, Coll Chem,Chem Biol Ctr,Minist Educ, Wuhan, Peoples R China.
关键词：
resistance;acetohydroxyacid synthase;antiresistance;P197L mutant;herbicidal activity
摘要：
BACKGROUND Intensifying weed resistance has challenged the use of existing acetohydroxyacid synthase (AHAS)-inhibiting herbicides. Hence, there is currently an urgent requirement for the discovery of a new AHAS inhibitor to effectively control AHAS herbicide-resistant weed species produced by target mutation. RESULTS To combat weed resistance caused by AHAS with P197L mutation, we built a structure library consisting of pyrimidinyl-salicylic acid derivatives. Using the pharmacophore-linked fragment virtual screening (PFVS) approach, hit compound 8 bearing 6-phenoxymethyl substituent was identified as a potential AHAS inhibitor with antiresistance effect. Subsequently, derivatives of compound 8 were synthesized and evaluated for their inhibitory activities. The study of the enzyme-based structure-activity relationship and structure-resistance relationship studies led to the discovery of a qualified candidate, 28. This compound not only significantly inhibited the activity of wild-type Arabidopsis thaliana (At) AHAS and P197L mutant, but also exhibited good antiresistance properties (RF = 0.79). Notably, compared with bispyribac at 37.5-150 g of active ingredient per hectare (g a.i. ha(-1)), compound 27 exhibited higher growth inhibition against both sensitive and resistant Descurainia sophia, CONCLUSION The title compounds have great potential to be developed as new leads to effectively control herbicide-resistant weeds comprising AHAS with P197L mutation. Also, our study provided a positive case for discovering novel, potent and antiresistance inhibitors using a fragment-based drug design approach. (c) 2020 Society of Chemical Industry
语种：
英文
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Discovery of Novel Pyrazole-Quinazoline-2,4-dione Hybrids as 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
作者：
He, Bo;Wu, Feng-Xu;Yu, Liang-Kun;Wu, Lei;Chen, Qiong;...
期刊：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY ,2020年68(18):5059-5067 ISSN：0021-8561
通讯作者：
Lin, Hong-Yan;Yang, Guang-Fu
作者机构：
[Yang, Guang-Fu; Yang, Wen-Chao; Lin, HY; Yang, GF; Chen, Qiong; Wu, Feng-Xu; Yu, Liang-Kun; Lin, Hong-Yan; He, Bo; Wu, Lei; Hao, Ge-Fei] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Int Joint Res Ctr Intelligent Biosensor Technol &, Minist Educ,Coll Chem, Wuhan 430079, Hubei, Peoples R China.;[Yang, Guang-Fu] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China.
通讯机构：
[Lin, HY; Yang, GF] C;[Yang, Guang-Fu] N;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Int Joint Res Ctr Intelligent Biosensor Technol &, Minist Educ,Coll Chem, Wuhan 430079, Hubei, Peoples R China.;Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China.
关键词：
Crystal structure;Metal ions;Metals;Scaffolds;4-Hydroxyphenylpyruvate dioxygenase;Active ingredients;Application rates;Broad spectrum;Cocrystal structure;Herbicidal activity;Hydrophobic residues;Quinazolines;Weed control;4 hydroxyphenylpyruvate dioxygenase;enzyme inhibitor;herbicide;plant protein;pyrazole;pyrazole derivative;quinazoline derivative;chemistry;drug effect;enzymology;metabolism;structure activity relation;weed;weed control;4-Hydroxyphenylpyruvate Dioxygenase;Enzyme Inhibitors;Herbicides;Plant Proteins;Plant Weeds;Pyrazoles;Quinazolines;Structure-Activity Relationship;Weed Control
摘要：
4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been identified as one of the most significant targets in herbicide discovery for resistant weed control. In a continuing effort to discover potent novel HPPD inhibitors, we adopted a ring-expansion strategy to design a series of novel pyrazole-quinazoline-2,4-dione hybrids based on the previously discovered pyrazole-isoindoline-1,3-dione scaffold. One compound, 3-(2-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,5-dimethylquinazoline-2,4(1H,3H)-dione (9bj), displayed excellent potency against AtHPPD, with an IC50 value of 84 nM, which is approximately 16-fold more potent than pyrasulfotole (IC50 = 1359 nM) and 2.7-fold more potent than mesotrione (IC50 = 226 nM). Furthermore, the co-crystal structure of the AtHPPD-9bj complex (PDB ID 6LGT) was determined at a resolution of 1.75 Å. Similar to the existing HPPD inhibitors, compound 9bj formed a bidentate chelating interaction with the metal ion and a π-πstacking interaction with Phe381 and Phe424. In contrast, o-chlorophenyl at the N3 position of quinazoline-2,4-dione with a double conformation was surrounded by hydrophobic residues (Met335, Leu368, Leu427, Phe424, Phe392, and Phe381). Remarkably, the greenhouse assay indicated that most compounds displayed excellent herbicidal activity (complete inhibition) against at least one of the tested weeds at the application rate of 150 g of active ingredient (ai)/ha. Most promisingly, compounds 9aj and 9bi not only exhibited prominent weed control effects with a broad spectrum but also showed very good crop safety to cotton, peanuts, and corn at the dose of 150 g of ai/ha. Copyright © 2020 American Chemical Society.
语种：
英文
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Design, Synthesis and Biological Activity of Pyrimidyl-Salicylate Derivatives Containing Alkoxy Moiety
作者：
Qu Renyu;Cai Zhuomei;Yang Jingfang;Liu Yuchao;Chen Qiong;...
期刊：
有机化学 ,2020年40(11):3953-3962 ISSN：0253-2786
通讯作者：
Yang Guangfu
作者机构：
[Chen Qiong; Cai Zhuomei; Liu Yuchao; Yang Jingfang; Qu Renyu; Yang Guangfu] Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensor Technol &, Coll Chem, Key Lab Pesticide & Chem Biol,Minist Educ, Wuhan 430079, Peoples R China.;[Niu Congwei; Xi Zhen] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.
通讯机构：
[Yang Guangfu] C;Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensor Technol &, Coll Chem, Key Lab Pesticide & Chem Biol,Minist Educ, Wuhan 430079, Peoples R China.
关键词：
乙酰羟酸合成酶;P197L突变体;反抗性;构象柔性;抗性杂草
摘要：
为寻找新型乙酰羟酸合成酶（EC2.2.1.6,AHAS）抑制剂以克服由靶标突变（P197L突变）所引起的杂草抗性问题,利用"构象柔性度分析"策略设计、合成了一系列烷氧基取代的嘧啶水杨酸衍生物.其中, 9个化合物对P197L突变型AHAS的抗性倍数（RF值）均小于等于1,在酶水平上具有良好的反抗性.特别是2-（（4,6-二甲氧基嘧啶-2-基）氧基）-6-（2-氟乙氧基）苯甲酸（5l）,被进一步确定为该系列最有效的反抗性AHAS抑制剂（RF=0.31）,不仅与氯磺隆（RF=2060）和双草醚（RF=4.57）相比抗性程度大幅降低,并且对野生型At AHAS和P197L突变体的抑制活性均达到了亚微摩尔水平,优于双草醚.此外,在150gai/ha的施用剂量下,2-（（4,6-二甲氧基嘧啶-2-基）氧基）-6-（2-（甲氧基）乙氧基）苯甲酸（5a）、2-（（4,6-二甲氧基嘧啶-2-基）氧基）-6-（3-（甲氧基）丙氧基）苯甲酸（5f）、2-（（4,6-二甲氧基嘧啶-2-基）氧基）-6-（2-氟乙氧基）苯甲酸（5l）和2-（（4,6-二甲氧基嘧啶-2-基）氧基）-6-（2,2-二氟乙氧基）苯甲酸（5m）对敏感型和抗性（P197L-AHAS）播娘蒿同时表现出优异的除草活性.值得注意的是,即使在最低剂量37.5 g ai/ha下,化合物5l对这两种杂草的除草防效仍超过85%,表现出良好的活体反抗性,具有深入研究的价值.
语种：
中文
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Pyrazole-Isoindoline-1,3-dione Hybrid: A Promising Scaffold for 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
作者：
He, Bo;Dong, Jin;Lin, Hong-Yan;Wang, Meng-Yao;Li, Xian-Kai;...
期刊：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY ,2019年67(39):10844-10852 ISSN：0021-8561
通讯作者：
Yang, Wen-Chao;Yang, Guang-Fu
作者机构：
[Li, Xian-Kai; Yang, Guang-Fu; Wang, Meng-Yao; Yang, Wen-Chao; Zheng, Bai-Feng; Dong, Jin; Chen, Qiong; Lin, Hong-Yan; He, Bo; Hao, Ge-Fei; Yang, WC; Yang, GF] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Key Lab Pesticide & Chem Biol,Minist Educ, Wuhan 430079, Hubei, Peoples R China.;[Li, Xian-Kai; Yang, Guang-Fu; Wang, Meng-Yao; Yang, Wen-Chao; Zheng, Bai-Feng; Dong, Jin; Chen, Qiong; Lin, Hong-Yan; He, Bo; Hao, Ge-Fei; Yang, WC; Yang, GF] Cent China Normal Univ, Coll Chem, Chem Biol Ctr, Wuhan 430079, Hubei, Peoples R China.;[Yang, Guang-Fu] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China.
通讯机构：
[Yang, WC; Yang, GF] C;[Yang, Guang-Fu] N;Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Key Lab Pesticide & Chem Biol,Minist Educ, Wuhan 430079, Hubei, Peoples R China.;Cent China Normal Univ, Coll Chem, Chem Biol Ctr, Wuhan 430079, Hubei, Peoples R China.;Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China.
关键词：
4-hydroxyphenylpyruvate dioxygenase;pyrazole;isoindoline-1,3-dione;inhibition kinetics;X-ray crystallography
摘要：
The discovery of 4-hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) inhibitors has been an active area of research due to their great potential as herbicides for weed control. Starting from the binding mode of known inhibitors of HPPD, a series of HPPD inhibitors with new molecular scaffolds were designed and synthesized by hybridizing 2-benzoylethen-1-ol and isoindoline-1,3-dione fragments. The results of the in vitro tests indicated that the newly synthesized compounds showed good HPPD inhibitory activity with IC50 values against the recombinant Arabidopsis thaliana HPPD (AtHPPD) ranging from 0.0039 ?M to over 1 ?M. Most promisingly, compound 4ae, 2-benzyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)isoindoline-1,3-dione, showed the highest AtHPPD inhibitory activity with a Ki value of 3.92 nM, making it approximately 10 times more potent than pyrasulfotole (Ki = 44 nM) and slightly more potent than mesotrione (Ki = 4.56 nM). In addition, the cocrystal structure of the AtHPPD-4ae complex was successfully resolved at a resolution of 1.8 Å. The X-ray diffraction analysis indicated that the two carbonyl groups of 2-benzoylethen-1-ol formed a bidentate chelating interaction with the metal ion, while the isoindoline-1,3-dione moiety formed pronounced π-π stacking interactions with Phe381 and Phe424. Moreover, water-mediated hydrogen bonding interactions were observed between Asn282 and the nitrogen atoms of the pyrazole ring of 4ae. The above results showed that the pyrazole-isoindoline-1,3-dione hybrid is a promising scaffold for developing HPPD inhibitors. © 2019 American Chemical Society. All rights reserved.
语种：
英文
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新型嘧啶-水杨酸类抑制剂的设计、合成及其生物活性研究
作者：
Qu Renyu;Yan Yaochao;Yang Jingfang;Chen Qiong* ;Yang Guangfu*
期刊：
有机化学 ,2019年39(8):2303-2310 ISSN：0253-2786
通讯作者：
Chen Qiong;Yang Guangfu
作者机构：
[Chen Qiong; Yang Guangfu; Yang Jingfang; Qu Renyu; Yan Yaochao] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
通讯机构：
[Chen, Q; Yang, GF] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
关键词：
乙酰羟酸合成酶;反抗性;P197L突变体;构象柔性;抗性杂草
摘要：
乙酰羟酸合成酶(Acetohydroxyacid synthase, AHAS)是一类重要的除草剂靶标,但是靶向AHAS的抑制剂是所有除草剂类型中抗性最为严重的一类,因此设计具有反抗性的AHAS抑制剂显得尤为必要.本工作基于前期低抗性AHAS抑制剂结构,利用“构象柔性度分析”的设计策略合理增加分子柔性,设计并合成了13个含“双氧桥”结构的嘧啶水杨酸类抑制剂.目标分子均经过氢谱(~1H NMR)、碳谱(~(13)C NMR)和高分辨质谱(HRMS)确证.酶水平活性结果显示,部分化合物对P197L突变体表现出了微摩尔水平的抑制作用,特别是2-((4,6-二甲氧基嘧啶-2-基)氧基)-6-(2-氟-4-硝基苯氧基)-4-甲基苯甲酸(61)对P197L突变体表现出了良好的反抗性.盆栽除草活性结果表明,个别化合物对抗性杂草播娘蒿具有一定的除草活性,其中2-((4,6-二甲氧基嘧啶-2-基)氧基)-6-(2-氟苯氧基)-4-甲基苯甲酸(6b)在150 g ai/ha浓度下,对敏感生物型播娘蒿和抗性播娘蒿均达到80%的除草防效,具有进一步深入研究的价值.
语种：
中文
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喹唑啉二酮衍生物的合成及生物活性研究
作者机构：
[杨光富; 何波; 王大伟; 陈琼] 华中师范大学化学学院农药与化学生物学教育部重点实验室;[杨光富; 何波; 王大伟; 陈琼] 南开大学化学学院元素有机化学国家重点实验室
会议名称：
中国化学会第30届学术年会
会议时间：
20160701
会议地点：
大连
会议论文集名称：
中国化学会第30届学术年会论文集
关键词：
HPPD酶;抑制剂;喹唑啉二酮;除草剂
摘要：
对羟苯基丙酮酸双加氧化酶（HPPD）是生物体内酪氨酸代谢过程中的一个关键酶,它能够将对羟基苯丙酮酸催化转化成尿黑酸。如果植物体内的HPPD被抑制,将会导致植物的光合作用过程受阻,进而导致其出现白化症状而死亡。因此,HPPD是一个重要的除草剂开发靶标。HPPD除草剂具有高效、低毒、作物安全性高、杀草谱广、对环境友好等一系列优点[2]。为了寻找新型的HPPD抑制剂,我们采用计算机辅助药物分子设计
语种：
中文
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Design, Synthesis, and Herbicidal Activity of Pyrimidine-Biphenyl Hybrids as Novel Acetohydroxyacid Synthase Inhibitors
作者：
Li, Ke-Jian;Qu, Ren-Yu;Liu, Yu-Chao;Yang, Jing-Fang;Devendar, Ponnam;...
期刊：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY ,2018年66(15):3773-3782 ISSN：0021-8561
通讯作者：
Yang, Guang-Fu;Xi, Zhen
作者机构：
[Yang, Jing-Fang; Yang, Guang-Fu; Devendar, Ponnam; Liu, Yu-Chao; Qu, Ren-Yu; Li, Ke-Jian; Chen, Qiong] CCNU, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Xi, Zhen; Niu, Cong-Wei] Nankai Univ NKU, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.;[Xi, Z; Yang, GF; Yang, Guang-Fu; Xi, Zhen] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.
通讯机构：
[Yang, Guang-Fu; Xi, Z; Yang, GF] C;[Xi, Zhen] N;CCNU, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;Nankai Univ NKU, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.;Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.
关键词：
Aromatic compounds;Herbicides;Lead compounds;Scaffolds;Acetohydroxyacid synthase;Arabidopsis thaliana;Herbicidal activity;Herbicide resistant weeds;Inhibitory activity;pyrimidine-biphenyl;Structure-based designs;Weed resistances;Weed control;acetolactate synthase;biphenyl;biphenyl derivative;enzyme inhibitor;herbicide;plant protein;pyrimidine derivative;antagonists and inhibitors;Arabidopsis;Brassicaceae;chemistry;drug design;drug effects;enzymology;kinetics;structure activity relation;synthesis;weed;weed control;Acetolactate Synthase;Arabidopsis;Biphenyl Compounds;Brassicaceae;Drug Design;Enzyme Inhibitors;Herbicides;Kinetics;Plant Proteins;Plant Weeds;Pyrimidines;Structure-Activity Relationship;Weed Control
摘要：
The issue of weed resistance to acetohydroxyacid synthase (EC 2.2.1.6, AHAS) inhibitors has become one of the largest obstacles for the application of this class of herbicides. In a continuing effort to discover novel AHAS inhibitors to overcome weed resistance, a series of pyrimidine-biphenyl hybrids (4aa-bb and 5aa-ah) were designed and synthesized via a scaffold hopping strategy. Among these derivatives, compounds 4aa (K<inf>i</inf>= 0.09 μM) and 4bb (K<inf>i</inf>= 0.02 μM) displayed higher inhibitory activities against Arabidopsis thaliana AHAS than those of the controls bispyribac (K<inf>i</inf>= 0.54 μM) and flumetsulam (K<inf>i</inf>= 0.38 μM). Remarkably, compounds 4aa, 4bb, 5ah, and 5ag exhibited excellent postemergence herbicidal activity and a broad spectrum of weed control at application rates of 37.5-150 g of active ingredient (ai)/ha. Furthermore, 4aa and 4bb showed higher herbicidal activity against AHAS inhibitor-resistant Descurainia sophia, Ammannia arenaria, and the corresponding sensitive weeds than that of bispyribac at 0.94-0.235 g ai/ha. Therefore, the pyrimidine-biphenyl motif and lead compounds 4aa and 4bb have great potential for the discovery of novel AHAS inhibitors to combat AHAS-inhibiting herbicide-resistant weeds.<br/> ©2018 American Chemical Society.
语种：
英文
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Recent Applications of Triazolopyrimidine-Based Bioactive Compounds in Medicinal and Agrochemical Chemistry
作者：
Qu Renyu;Liu Yuchao;Wishwajith, W. M.;Kandegama, W.;Qiong, Chen* ;...
期刊：
MINI-REVIEWS IN MEDICINAL CHEMISTRY ,2018年18(9):781-793 ISSN：1389-5575
通讯作者：
Qiong, Chen
作者机构：
[Qiong, Chen; Liu Yuchao; Wishwajith, W. M.; Kandegama, W.; Qu Renyu; Yang Guangfu] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Qiong, Chen] Cent China Normal Univ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.
通讯机构：
[Qiong, Chen] C;Cent China Normal Univ, Coll Chem, Wuhan 430079, Hubei, Peoples R China.
关键词：
5 amino 2 (2 furyl) 7 (2 phenylethyl)pyrazolo[4,3 e][1,2,4]triazolo[1,5 c]pyrimidine;adenosine receptor blocking agent;cisplatin;dihydroorotate dehydrogenase;dihydroorotate dehydrogenase inhibitor;doxorubicin;enzyme inhibitor;prednisolone;pyrimidine derivative;adenosine receptor blocking agent;agricultural chemical;antiinfective agent;antineoplastic agent;antiparasitic agent;enzyme inhibitor;nonsteroid antiinflammatory agent;pyrimidine derivative;antibacterial activity;antifungal activity;antiinflammatory activity;antineoplastic activity;asthma;biological activity;drug effect;drug efficacy;drug mechanism;drug potency;drug screening;drug selectivity;drug structure;drug synthesis;EC50;human;IC50;minimum inhibitory concentration;nonhuman;Parkinson disease;Review;chemical structure;chemistry;structure activity relation;synthesis;Agrochemicals;Anti-Bacterial Agents;Anti-Inflammatory Agents, Non-Steroidal;Antineoplastic Agents;Antiparasitic Agents;Enzyme Inhibitors;Molecular Structure;Purinergic P1 Receptor Antagonists;Pyrimidines;Structure-Activity Relationship
摘要：
The triazolopyrimidine ring is a ubiquitous structural feature of many active compounds with diversified pharmacology efficacy. These structures have aroused our / researchers interests in the development of novel compounds with anticancer, anti-inflammatory, antibacterial, antifungal, and other activities. A large number of published literatures were reviewed during the last few decades. This review contains various pharmacological and agrochemical activities of triazolopyrimidine and it may be regarded as the lead compound for the new research towards future medicinal and agrochemical development.
语种：
英文
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Single Nanochannel Platform for Detecting Chiral Drugs
作者：
Boussouar, Imene;Chen, Qianjin;Chen, Xue;Zhang, Yulun;Zhang, Fan;...
期刊：
Analytical Chemistry ,2017年89(2):1110-1116 ISSN：0003-2700
通讯作者：
Li, Haibing
作者机构：
[Boussouar, Imene; Li, Haibing; Zhang, Fan; Tian, Demei; Chen, Xue] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol CCNU, Minist Educ, Wuhan 430079, Peoples R China.;[Zhang, Yulun; White, Henry S.; Chen, Qianjin] Univ Utah, Dept Chem, 315 S,1400 E, Salt Lake City, UT 84112 USA.
通讯机构：
[Li, Haibing] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol CCNU, Minist Educ, Wuhan 430079, Peoples R China.
摘要：
Chiral drugs play an essential role in medical and biochemical systems, and thus enantioselective analysis of chiral molecules has become a central focus in chemical, biological, medical, and pharmaceutical research. The design of chiral drug-detecting systems is a long-term and challenging task. Here we report the use of a modification-free nanochannel method for enantioselective recognition of S-naproxen from R-naproxen using N-acetyl-L-cysteine-capped gold nanoparticles as a chiral selector. The chiral discrimination is based on a drug-induced nanoparticle diastereoselective aggregation mechanism that blocks ion transport through the nanochannel. We demonstrated that high S-Npx selectivity in both water and biological samples can be achieved. This simple method has potential applications as a general platform for the detection of chiral molecules. © 2016 American Chemical Society.
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英文
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Computational Discovery of Potent and Bioselective Protoporphyrinogen IX Oxidase Inhibitor via Fragment Deconstruction Analysis
作者：
Hao, Ge-Fei;Zuo, Yang;Yang, Sheng-Gang;Chen, Qian;Zhang, Yue;...
期刊：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY ,2017年65(28):5581-5588 ISSN：0021-8561
通讯作者：
Yang, Guang-Fu;Xi, Zhen
作者机构：
[Yang, Sheng-Gang; Yang, Guang-Fu; Zhang, Yue; Yin, Chun-Yan; Zuo, Yang; Hao, Ge-Fei; Chen, Qian] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Xi, Zhen; Niu, Cong-Wei] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.;[Xi, Z; Yang, GF; Yang, Guang-Fu; Xi, Zhen] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China.
通讯机构：
[Yang, Guang-Fu; Xi, Z; Yang, GF] C;[Xi, Zhen] N;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.;Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China.
关键词：
fragment;PPO;enzyme inhibitors;herbicides;bioselectivity
摘要：
Tuning the binding selectivity through appropriate ways is a primary goal in the design and optimization of a lead toward agrochemical discovery. However, how to achieve rational design of selectivity is still a big challenge. Herein, we developed a novel computational fragment generation and coupling (CFGC) strategy that led to a series of highly potent and bioselective inhibitors targeting protoporphyrinogen IX oxidase. This enzyme plays a vital role in heme and chlorophyll biosynthesis, which has been proven to be associated with many drugs and agrochemicals. However, existing agrochemicals are nonbioselective, resulting in a great threat to nontargeted organisms. To the best of our knowledge, this is the first bioselective inhibitor targeting the tetrapyrrole biosynthesis pathway. In addition, the candidate showed excellent in vivo bioactivity and much better safety toward humans.
语种：
英文
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微波辅助下高效合成功能性6-芳基水杨酸类衍生物
作者：
曲仁渝;陈念;刘玉超;陈琼;杨光富
（ 期刊：
有机化学 ,2017年37(5):1266-1272 ISSN：0253-2786
通讯作者：
Yang Guangfu
作者机构：
[杨光富; 陈琼; 刘玉超; 曲仁渝; 陈念] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构：
[Yang Guangfu] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
关键词：
Functionalized 6-arylsalicylates;Suzuki cross-coupling reactions;Microwave irradiation;Electronic effect
摘要：
Functionalized 6-arylsalicylate substructures occur in a variety of pharmacologically relevant natural products and bioactive compounds. Especially 6-arylsubstituted salicylates, as a key pharmacophore of anti-resistant acetohydroxyacid synthase (AHAS) inhibitors have played a lead role in combatting the weed-resistance issues. Previously, we have explored two new methods to synthesize position-6 aryl substituted salicylic acid fragment. However, these two methods failed to introduce various substituents into salicylic acid. Here an efficient method for the synthesis of 6-substituted salicylates is described via a microwave-promoted Suzuki cross-coupling. Due to the obvious advantages of this method, such as a wide range of substrates, smooth and rapid reaction and moderate to excellent yields, this protocol could be utilized to synthesize more anti-resistant AHAS inhibitors.
语种：
英文
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Computational design of novel inhibitors to overcome weed resistance associated with acetohydroxyacid synthase (AHAS) P197L mutant
作者：
Qu, Ren-Yu;Yang, Jing-Fang;Liu, Yu-Chao;Chen, Qiong;Hao, Ge-Fei;...
期刊：
Pest Management Science ,2017年73(7):1373-1381 ISSN：1526-498X
通讯作者：
Yang, Guang-Fu
作者机构：
[Yang, Guang-Fu; Yang, Jing-Fang; Liu, Yu-Chao; Qu, Ren-Yu; Chen, Qiong; Hao, Ge-Fei] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Xi, Zhen; Niu, Cong-Wei] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.;[Yang, Guang-Fu; Xi, Zhen] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China.;[Yang, Guang-Fu] Cent China Normal Univ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构：
[Yang, Guang-Fu] C;Cent China Normal Univ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词：
herbicide;weed resistance;fragment-based drug discovery;acetohydroxyacid synthase;pyrimidinyl salicylic acid
摘要：
BACKGOUND: Acetohydroxyacid synthase (AHAS; EC 2.2.1.6) is the first common enzyme in the biosynthetic pathway leading to the branched-chain amino acids in plants and a wide range of microorganisms. With the long-term and wide application of AHAS inhibitors, weed resistance is becoming a global problem, which leads to an urgent demand for novel inhibitors to antagonize both wild-type and resistant AHAS. RESULTS: Pyrimidinyl salicylic acid derivatives, as one of the main classes of commercial AHAS herbicides, show potential anti-resistant bioactivity to wild-type and P197L mutant. In current work, a series of novel 2-benzoyloxy-6-pyrimidinyl salicylic acid derivatives were designed through fragment-based drug discovery. Fortunately, the newly synthesized compounds showed good inhibitory activity against both wild-type and P197L mutant. Some compounds not only had a lower resistance factor value but also showed excellent inhibitory activity against wild-type AHAS and P197L mutant. Furthermore, greenhouse experiments showed compound 11m displayed almost 100% inhibition against both wild-type and high-resistant Descurainia sophia at a dosage of 150 g a.i. ha−1. CONCLUSION: The present work indicated that the 2-benzoyloxy-6-pyrimidinyl salicylic acid motif was well worth further optimization. Also, compound 11m could be used as a potential anti-resistant AHAS herbicide, which requires further research. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry
语种：
英文
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对羟基苯丙酮酸双加氧酶(HPPD)的结构及其吡唑类除草剂的最新研究进展
作者：
He, Bo;Wang, Dawei;Yang, Wenchao;Chen, Qiong;Yang, Guangfu
* （ 期刊：
有机化学 ,2017年37(11):2895-2904 ISSN：0253-2786
作者机构：
[Yang, Guangfu; Yang, Wenchao; Chen, Qiong; He, Bo] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.;[Wang, Dawei] Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.
通讯机构：
[Yang, Guangfu] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.
关键词：
对羟基苯丙酮酸双加氧酶;作用机制;结合位点;除草剂
摘要：
对羟基苯丙酮酸双加氧酶(EC 1.13.11.27,HPPD)是重要的除草剂靶标.以HPPD为靶标的除草剂具有高效、低毒、作物安全性高、不易产生抗性、环境相容性好及对后茬作物安全等一系列优点.结合最新的研究进展,详细综述了HPPD的结构,并针对吡唑类HPPD除草剂的作用模式、在生物体内的作用机制和代谢途径以及研究现状进行了总结与分析.
语种：
中文
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Discovery of New 2-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)oxy]-6-(substituted phenoxy)benzoic Acids as Flexible Inhibitors of Arabidopsis thaliana Acetohydroxyacid Synthase and Its P197L Mutant
作者：
Qu, Ren-Yu;Yang, Jing-Fang;Devendar, Ponnam;Kang, Wei-Ming;Liu, Yu-Chao;...
期刊：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY ,2017年65(51):11170-11178 ISSN：0021-8561
通讯作者：
Yang, Guang-Fu;Xi, Zhen
作者机构：
[Yang, Guang-Fu; Devendar, Ponnam; Kang, Wei-Ming; Liu, Yu-Chao; Qu, Ren-Yu; Chen, Qiong; Yang, Jing-Fang] Cent China Normal Univ CCNU, Minist Educ, Key Lab Pesticide & Chem Biol, Coll Chem, Wuhan 430079, Hubei, Peoples R China.;[Xi, Zhen; Niu, Cong-Wei] Nankai Univ NKU, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.;[Yang, Guang-Fu; Xi, Z; Yang, GF; Xi, Zhen] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.
通讯机构：
[Yang, Guang-Fu; Xi, Z; Yang, GF] C;[Xi, Zhen] N;Cent China Normal Univ CCNU, Minist Educ, Key Lab Pesticide & Chem Biol, Coll Chem, Wuhan 430079, Hubei, Peoples R China.;Nankai Univ NKU, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.;Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.
关键词：
Fighter aircraft;Plants (botany);Scaffolds;Weed control;antiresistance property;Herbicidal activity;Molecular docking;P197L mutant;Structure activity relationships;Benzoic acid;acetolactate synthase;Arabidopsis protein;benzoic acid derivative;enzyme inhibitor;herbicide;Arabidopsis;chemistry;enzymology;genetics;kinetics;metabolism;missense mutation;molecular docking;structure activity relation;Acetolactate Synthase;Arabidopsis;Arabidopsis Proteins;Benzoates;Enzyme Inhibitors;Herbicides;Kinetics;Molecular Docking Simulation;Mutation, Missense;Structure-Activity Relationship
摘要：
In the search for new antiresistance acetohydroxyacid synthase (AHAS, EC 2.2.1.6) inhibitors to combat weed resistance associated with AHAS mutations, a series of 2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)oxy]-6-(substituted phenoxy)benzoic acids 11-38 were designed and synthesized via the strategy of conformational flexibility analysis. Compounds 21, 22, 26, 33, 36, and 38 with high potency against both wild-type AtAHAS and its P197L mutant were identified as promising candidates with low resistance factors (RF, defined as the ratio between the k<inf>i</inf>values toward P197L mutant and wild-type AHAS) ranging from 0.73 to 6.32. Especially, compound 22 (RF = 0.73) was further identified as the most potent antiresistance AHAS inhibitor because of its significantly reduced resistance level compared with that of tribenuron-methyl (RF = 2650) and bispyribac (RF = 4.57). Furthermore, compounds 26, 33, 36, and 38 also displayed promising herbicidal activities against sensitive and resistant (P197L) Descurainia sophia at the dosage of 75-150 g of active ingredient (ai)/ha. Notably, compounds 33 and 38 still maintained over 60% herbicidal activity toward the resistant weed even at much lower dosages (37.5 g ai/ha). Therefore, the designed scaffold has the great potential to discover new candidate compounds for the control of weed resistance associated with AHAS mutation.<br/> ©2017 American Chemical Society.
语种：
英文
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吡唑类HPPD除草剂的最新研究进展
作者机构：
[杨光富; 何波; 王大伟; 陈琼] 华中师范大学化学学院农药与化学生物学教育部重点实验室;[杨光富; 何波; 王大伟; 陈琼] 南开大学化学学院元素有机化学国家重点实验室
会议名称：
中国化工学会农药专业委员会第十七届年会
会议时间：
2016-07-28
会议地点：
中国河南郑州
关键词：
对羟基苯丙酮酸双加氧化酶;作用机制;结合位点;除草剂
摘要：
对羟基苯丙酮酸双加氧化酶(EC 1.13.11.27,HPPD)作为除草剂靶标,具有高效,低毒,作物安全性高,不易产生抗性、环境相容性好及对后茬作物安全等一系列优点。本文详细介绍了HPPD的结构、抑制剂的作用位点以及其在生物体内的作用机制和代谢产物,同时对商品化吡唑类HPPD除草剂的特点及目前的研究现状进行总结分析。
语种：
中文
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Synthesis and absolute configuration assignment of albucidin: a late-stage reductive deiodination by visible light photocatalysis
作者：
Zhang, Hu;Liu, Peng-Fei;Chen, Qiong;Wu, Qiong-You;Seville, Anne;...
期刊：
Organic & Biomolecular Chemistry ,2016年14(13):3482-3485 ISSN：1477-0520
通讯作者：
Yang, Guang-Fu
作者机构：
[Wu, Qiong-You; Yang, Guang-Fu; Zhang, Hu; Liu, Peng-Fei; Chen, Qiong; Zhoua, Shao-Lin] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Clough, John; Seville, Anne; Gu, Yu-Cheng] Syngenta Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England.
通讯机构：
[Yang, Guang-Fu] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词：
Catalysis;Photocatalysis;Absolute configuration;Deiodination;Late stage;Old structure;Structural modifications;Visible-light photocatalysis;Light;albucidin;nucleoside;catalysis;chemical structure;chemistry;light;molecular model;oxidation reduction reaction;photochemistry;radiation response;synthesis;Catalysis;Light;Models, Molecular;Molecular Structure;Nucleosides;Oxidation-Reduction;Photochemical Processes
摘要：
The synthesis of albucidin and its enantiomer are described. It involves a visible-light photocatalysis deiodination at the late stage. The absolute configuration of natural albucidin is determined as (1R,3S). This work provides a basis for structural modification to develop a new type of herbicidal from an old structure.
语种：
英文
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An Efficient One-Pot Synthesis of 2-(Aryloxyacetyl)cyclohexane-1,3-diones as Herbicidal 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
作者：
Wang, Da-Wei;Lin, Hong-Yan;He, Bo;Wu, Feng-Xu;Chen, Tao;...
期刊：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY ,2016年64(47):8986-8993 ISSN：0021-8561
通讯作者：
Yang, Wen-Chao;Yang, Guang-Fu
作者机构：
[Yang, Guang-Fu; Yang, Wen-Chao; Chen, Tao; Chen, Qiong; Wang, Da-Wei; Lin, Hong-Yan; Wu, Feng-Xu; He, Bo; Yang, WC; Yang, GF] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;[Yang, Guang-Fu] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.
通讯机构：
[Yang, WC; Yang, GF; Yang, Guang-Fu] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.;Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.
关键词：
Acetone;Crops;Cyclohexane;Herbicides;4-Hydroxyphenylpyruvate dioxygenase;Herbicidal activity;One-pot synthesis;Structure activity relationships;Triketone;Weed control;2-(2-((1-bromonaphthalen-2-yl)oxy)acetyl)-3-hydroxycyclohex-2-en-1-one;4 hydroxyphenylpyruvate dioxygenase;acetone cyanohydrin;cyclohexanone derivative;enzyme inhibitor;ethylamine;herbicide;imidazole derivative;mesotrione;N,N-carbonyldiimidazole;naphthalene derivative;nitrile;triethylamine;antagonists and inhibitors;Arabidopsis;Brassica rapa;chemical structure;chemistry;dose response;drug effects;maize;metabolism;structure activity relation;synthesis;weed;weed control;4-Hydroxyphenylpyruvate Dioxygenase;Arabidopsis;Brassica rapa;Cyclohexanones;Dose-Response Relationship, Drug;Enzyme Inhibitors;Ethylamines;Herbicides;Imidazoles;Molecular Structure;Naphthalenes;Nitriles;Plant Weeds;Structure-Activity Relationship;Weed Control;Zea mays
摘要：
4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is an important target for new bleaching herbicides discovery. As a continuous work to discover novel crop selective HPPD inhibitor, a series of 2-(aryloxyacetyl)cyclohexane-1,3-diones were rationally designed and synthesized by an efficient one-pot procedure using N,N′-carbonyldiimidazole (CDI), triethylamine, and acetone cyanohydrin in CH<inf>2</inf>Cl<inf>2</inf>. A total of 58 triketone compounds were synthesized in good to excellent yields. Some of the triketones displayed potent in vitro Arabidopsis thaliana HPPD (AtHPPD) inhibitory activity. 2-(2-((1-Bromonaphthalen-2-yl)oxy)acetyl)-3-hydroxycyclohex-2-en-1-one, II-13, displayed high, broad-spectrum, and postemergent herbicidal activity at the dosage of 37.5-150 g ai/ha, nearly as potent as mesotrione against some weeds. Furthermore, II-13 showed good crop safety against maize and canola at the rate of 150 g ai/ha, indicating that II-13 might have potential as a herbicide for weed control in maize and canola fields. II-13 is the first HPPD inhibitor showing good crop safety toward canola. ©2016 American Chemical Society.
语种：
英文
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Triazolopyrimidines as a New Herbicidal Lead for Combating Weed Resistance Associated with Acetohydroxyacid Synthase Mutation
作者：
Liu, Yu-Chao;Qu, Ren-Yu;Chen, Qiong;Yang, Jing-Fang;Cong-Wei, Niu;...
期刊：
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY ,2016年64(24):4845-4857 ISSN：0021-8561
通讯作者：
Yang, Guang-Fu
作者机构：
[Yang, Guang-Fu; Yang, Jing-Fang; Liu, Yu-Chao; Chen, Qiong] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Yang, Guang-Fu; Zhen, Xi; Cong-Wei, Niu] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.;[Yang, Guang-Fu; Zhen, Xi] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.
通讯机构：
[Yang, Guang-Fu] C;[Yang, Guang-Fu] N;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China.;Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 30071, Peoples R China.
关键词：
molecular design;herbicide;weed resistance;acetohydroxyacid synthase;triazolopyrimidines
摘要：
Acetohydroxyacid synthase (AHAS;also known as acetolactate synthase;EC 2.2.1.6, formerly EC 4.1.3.18) is the first common enzyme in the biosynthetic pathway leading to the branched-chain amino acids in plants and a wide range of microorganisms. Weed resistance to AHAS-inhibiting herbicides, increasing at an exponential rate, is becoming a global problem and leading to an urgent demand of developing novel compounds against both resistant and wild AHAS. In the present work, a series of novel 2-aroxyl-1,2,4-triazolopyrimidine derivatives (a total of 55) were designed and synthesized with the aim to discover an antiresistant lead compound. Fortunately, the screening results indicated that many of the newly synthesized compounds showed a better, even excellent, inhibition effect against both the wild-type Arabidopsis thaliana AHAS and P197L mutants. Among them, compounds 5-3 to 5-17, compounds 5-19 to 5-26, compounds 5-28 to 5-45, and compound 5-48 have the lower values of resistance factor (RF) and display a potential power to overcome resistance associated with the P197L mutation in the enzyme levels. Further greenhouse in vivo assay showed that compounds 5-15 and 5-20 displayed "moderate" to "good" herbicidal activity against both the wild type-and the resistant (P197L mutation) Descurainia sophia, even at a rate as low as 0.9375 (g of ai/ha). The above results indicated that these two compounds could be used as new leads for the future development of antiresistance herbicides. ©2016 American Chemical Society.
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英文
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