Design, syntheses and biological activity of novel ALS inhibitors (IX)

Yang, Guang‐Fu; Liu, Huayin; Yang, Xiufeng; Yang, Hai‐Tao

doi:10.1007/bf02874332

Cited by 10 publications

(7 citation statements)

References 7 publications

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“…Previously published 3D-QSAR analyses of sulfonylurea herbicides [19][20][21][22][23][24][25][26] suffer from several shortcomings. Firstly, the assumed bioactive conformation was based on either the structures of sulfonylureas crystallized as free molecules [20][21][22][23]25] or their low energy conformers calculated theoretically [19,24,26].…”

Section: D-qsar Analysesmentioning

confidence: 99%

“…However, it is now known that none of these conformations match that observed when a sulfonylurea is bound to its target enzyme [7,8]. Secondly, most activity data employed in previous QSAR investigations were obtained using in vivo experiments [19][20][21][22][23][24][25][26]. Herbicidal activity depends ultimately upon inhibition of AHAS, but there are differences between in vivo and in vitro effects of these compounds due to barriers between the site of application and the intracellular target, degradation and detoxification by the plant, and so on.…”

Section: D-qsar Analysesmentioning

confidence: 99%

“…Firstly, the assumed bioactive conformation was based on either the structures of sulfonylureas crystallized as free molecules [20][21][22][23]25] or their low energy conformers calculated theoretically [19,24,26]. However, it is now known that none of these conformations match that observed when a sulfonylurea is bound to its target enzyme [7,8].…”

Section: D-qsar Analysesmentioning

confidence: 99%

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Structure-activity relationships for a new family of sulfonylurea herbicides

Wang

et al. 2005

J Comput Aided Mol Des

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Acetohydroxyacid synthase (AHAS; EC 2.2.1.6) catalyzes the first common step in branched-chain amino acid biosynthesis. The enzyme is inhibited by several chemical classes of compounds and this inhibition is the basis of action of the sulfonylurea and imidazolinone herbicides. The commercial sulfonylureas contain a pyrimidine or a triazine ring that is substituted at both meta positions, thus obeying the initial rules proposed by Levitt. Here we assess the activity of 69 monosubstituted sulfonylurea analogs and related compounds as inhibitors of pure recombinant Arabidopsis thaliana AHAS and show that disubstitution is not absolutely essential as exemplified by our novel herbicide, monosulfuron (2-nitro-N-(4'-methyl-pyrimidin-2'-yl) phenyl-sulfonylurea), which has a pyrimidine ring with a single meta substituent. A subset of these compounds was tested for herbicidal activity and it was shown that their effect in vivo correlates well with their potency in vitro as AHAS inhibitors. Three-dimensional quantitative structure-activity relationships were developed using comparative molecular field analysis and comparative molecular similarity indices analysis. For the latter, the best result was obtained when steric, electrostatic, hydrophobic and H-bond acceptor factors were taken into consideration. The resulting fields were mapped on to the published crystal structure of the yeast enzyme and it was shown that the steric and hydrophobic fields are in good agreement with sulfonylurea-AHAS interaction geometry.

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Section: D-qsar Analysesmentioning

confidence: 99%

Section: D-qsar Analysesmentioning

confidence: 99%

Section: D-qsar Analysesmentioning

confidence: 99%

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Structure-activity relationships for a new family of sulfonylurea herbicides

Wang

et al. 2005

J Comput Aided Mol Des

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“…The dihedral angle between this plane and the benzene ring is 114.3 (2) . The bond lengths involving atom C7 indicate a degree of electron delocalization (Yang et al, 1999). Selected bond lengths and angles are listed in Table 1 and a packing diagram is shown in Fig.…”

Section: Commentmentioning

confidence: 99%

2-tert-Butylamino-1-(4-chlorophenyl)-4,4-dimethyl-1H-imidazolin-5(4H)-one

2006

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“…The C7-C8 bond length of 1.347 (2) Å is close to that of a typical C C bond (1.35 Å ), whereas the N1-C10 bond length of 1.3047 (19) Å , is slightly longer than that of a typical C N bond (1.28 Å ). The N3-C10, N2-C10, N2-C11 and N2-C9 bond lengths [1.3292 (19), 1.4004 (18), 1.426 (2) and 1.3860 (19) Å , respectively] indicate some degree of delocalization around the ring system (Yang et al, 1999). The C6-C7-C8-N1 torsion angle of 0.6 (3) indicates a Z configuration of the molecule about the C7 C8 bond.…”

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confidence: 99%