4'-乙酰氨基苯基 4-胍基苯甲酸酯盐酸盐 | 79119-49-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 4'-乙酰氨基苯基 4-胍基苯甲酸酯盐酸盐
• 中文别名: 4'-乙酰氨基苯基4-胍基苯甲酸酯盐酸盐
• 英文名称: 4-((Aminoiminomethyl)amino)benzoic acid 4-(acetylamino)phenyl ester hydrochloride
• 英文别名: 4'-Acetamidophenyl 4-guanidinobenzoate hydrochloride；[4-(4-acetamidophenoxy)carbonylphenyl]-(diaminomethylidene)azanium;chloride
• CAS: 79119-49-6
• 化学式: C₁₆H₁₆N₄O₃*ClH
• 分子量: 348.789
• InChiKey: CBYYAOPEHXAUHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对乙酰氨基酚 、 4-胍基苯甲酸盐酸盐 在 吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到4'-乙酰氨基苯基 4-胍基苯甲酸酯盐酸盐
  参考文献：
  名称：

  Synthesis and inhibition of human acrosin and trypsin and acute toxicity of aryl 4-guanidinobenzoates

  摘要：

  The aryl 4-guanidinobenzoate, 4'-nitrophenyl 4-guanidinobenzoate (NPGB), is a potent inhibitor of sperm acrosin, an enzyme with an essential function in the fertilization process. NPGB prevents fertilization in a number of animal species and is a good lead compound for the development of contraceptive agents. In order to assess the efficacy of other aryl 4-guanidinobenzoates as acrosin inhibitors, 24 of these compounds were synthesized. Their inhibitory activity toward human acrosin was determined and compared with their activity toward human pancreatic trypsin in order to assess whether inhibitor sensitivity differed between these similar enzymes. Nine of the inhibitors were synthesized from phenols approved by the FDA for therapeutic use. The acute toxicity of these inhibitors in mice was determined and compared to that of nonoxynol-9, the most commonly used active ingredient in today's vaginal contraceptive preparations. All of the compounds proved to be potent inhibitors of human acrosin although 3 orders of magnitude difference were observed between the most and least effective inhibitors. Little specificity was present in regard to their inhibition of acrosin and trypsin. All the aryl 4-guanidinobenzoates synthesized from FDA-approved phenols were less toxic than nonoxynol-9, and it is concluded that these 4-guanidinobenzoates are of interest for further development and testing as nonhormonal contraceptive agents.

  DOI：

  10.1021/jm00154a015

文献信息

• KAMINSKI, J. M.;BAUER, L.;ZANEVELD, L.
  作者：KAMINSKI, J. M.、BAUER, L.、ZANEVELD, L.

  DOI：——

  日期：——
• US4423069A
  申请人：——

  公开号：US4423069A

  公开（公告）日：1983-12-27