N-phenylsulfonyl (3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexenecarboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-phenylsulfonyl (3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexenecarboxamide
• 英文别名: (3R,4R,5S)-4-acetamido-N-(benzenesulfonyl)-5-(diaminomethylideneamino)-3-pentan-3-yloxycyclohexene-1-carboxamide
• 化学式: C₂₁H₃₁N₅O₅S
• 分子量: 465.574
• InChiKey: AMAXGSNGTPZEHY-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  174
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3R,4R,5S)-4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid 在 4-二甲氨基吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-phenylsulfonyl (3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexenecarboxamide
  参考文献：
  名称：

  Oseltamivir hydroxamate and acyl sulfonamide derivatives as influenza neuraminidase inhibitors

  摘要：

  Tamiflu, the ethyl ester form of oseltamivir carboxylic acid (OC), is the first orally available anti-influenza drug for the front-line therapeutic option. In this study, the OC-hydroxamates, OC-sulfonamides and their guanidino congeners (GOC) were synthesized. Among them, an OC-hydroxamate 7d bearing an O-(2-indolyl)propyl substituent showed potent NA inhibition (IC50 = 6.4 nM) and good anti-influenza activity (EC50 = 60.1 nM) against the wild-type H1N1 virus. Two GOC-hydroxamates (9b and 9d) and one GOC-sulfonamide (12a) were active to the tamiflu-resistant H275Y virus (EC50 = 2.3-6.9 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.10.005

文献信息

• Oseltamivir hydroxamate and acyl sulfonamide derivatives as influenza neuraminidase inhibitors
  作者：Bei-Tao Hong、Chun-Lin Chen、Jim-Min Fang、Keng-Chang Tsai、Shi-Yun Wang、Wen-I Huang、Yih-Shyun E. Cheng、Chi-Huey Wong

  DOI：10.1016/j.bmc.2014.10.005

  日期：2014.12

  Tamiflu, the ethyl ester form of oseltamivir carboxylic acid (OC), is the first orally available anti-influenza drug for the front-line therapeutic option. In this study, the OC-hydroxamates, OC-sulfonamides and their guanidino congeners (GOC) were synthesized. Among them, an OC-hydroxamate 7d bearing an O-(2-indolyl)propyl substituent showed potent NA inhibition (IC50 = 6.4 nM) and good anti-influenza activity (EC50 = 60.1 nM) against the wild-type H1N1 virus. Two GOC-hydroxamates (9b and 9d) and one GOC-sulfonamide (12a) were active to the tamiflu-resistant H275Y virus (EC50 = 2.3-6.9 mu M). (C) 2014 Elsevier Ltd. All rights reserved.