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Synthesis of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine. Inhibitors of rhinovirus multiplication.
Journal of Medicinal Chemistry ( IF 6.8 ) Pub Date : 1980-04-01 , DOI: 10.1021/jm00178a004
J. H. Wikel , C. J. Paget , D. C. DeLong , J. D. Nelson , C. Y. E. Wu , J. W. Paschal , A. Dinner , R. J. Templeton , M. O. Chaney

The synthesis and antirhinovirus activity of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine (4 and 5) are reported. The structural assignments of 4 and 5 are based upon 13C NMR spectra of both isomers and also X-ray analysis of 5. The anti-isomer 5 was more potent than the syn-isomer 4 when compared as an inhibitor of rhinovirus multiplication in vitro. Both isomers inhibited multiplication of 15 different serotypes of rhinovirus.

中文翻译:

6-[[[(羟基亚氨基)苯基]甲基] -1-[(1-甲基乙基)磺酰基] -1H-苯并咪唑-2-胺的正反异构体的合成。鼻病毒繁殖抑制剂。

报道了6-[[[(羟基亚氨基)苯基]甲基] -1-[(1-甲基乙基)磺酰基] -1H-苯并咪唑-2-胺(4和5)的顺式和反式异构体的合成和抗鼻病毒活性。4和5的结构分配基于两种异构体的13 C NMR光谱以及5的X射线分析。与之相比,抗异构体5在体外作为鼻病毒繁殖抑制剂比同型异构体4更有效。两种异构体均抑制了15种不同血清型的鼻病毒的繁殖。
更新日期:2019-11-01
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