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Guo Feng ZHAO, Hua Zheng YANG, Yong Hong LI. Bioisostere of Sulfonyl Moiety-The Synthesis of New ALS Inhibitors N-(Asymmetry Disubstituted Phosphoryl)-N'-(4,6-dimethoxypyrimidin-2-yl) Ureas[J]. Chinese Chemical Letters,
;1998, 9(5): 455-458.
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In view of the isosterism of the sulfonyl (-S02-) and phosphoryl groups [-P(0)(0R)-, R=H, CH3, C2H5, etc], two new types of ureas, N-(N-aryl-O-alkyl phosphoryl)-N'-(4, 6-dimethoxy pyrimidin-2-yl) ureas 2 and N-(N-aryI-N-alkyl phosphoryl)-N'-(4, 6-dimethoxy pyrimidin-2-yl) ureas 3,were synthesized by treating N-(arylaminochlorophosphoryl)-N'-(4,6-dimethoxy pyrimidinyl-2-) ureas 4 with alcohols or amines. Compounds 4 were obtained by reacting dichlorophosphoryl isocyanate with 4,6-dimethoxy-2-aminopyrimidine, and then with aromatic amines. The enzyme tests (in vitro) indicated that compounds 2 and 3 were two novel classes of acetolactate synthase (ALS) inhibitors, which showed that the phosphoryl group, [-P(0)(0R)-], or[-P(0)(NHR)-], was a good bioisostere of the sulfonyl group (-S02-) in sulfonylurea.
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Keywords:
- isosterism,
- bioisostere,
- sulfonyl,
- phosphoryl,
- sulfonylurea,
- ALS inhibitor
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