2'-甲氧羰基苯基4-胍基苯甲酸酯 | 89022-11-7

• 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: 2'-甲氧羰基苯基4-胍基苯甲酸酯
• 中文别名: 4-((氨基亚氨基甲基)氨基)苯甲酸2-(甲氧基羰基)苯酯；4H-吡啶并[1,2-a]嘧啶-4-酮,9-溴-7-甲基-2-(4-吗啉基)-
• 英文名称: 2'-Carbomethoxyphenyl 4-guanidinobenzoate
• 英文别名: methyl 2-[4-(diaminomethylideneamino)benzoyl]oxybenzoate
• CAS: 89022-11-7
• 化学式: C₁₆H₁₅N₃O₄
• 分子量: 313.313
• InChiKey: QFHVTOHRBHBYIA-UHFFFAOYSA-N

物化性质

• 沸点：
  453.12°C (rough estimate)
• 密度：
  1.2053 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2925290090
• 储存条件：
  库房应保持低温、通风和干燥。

制备方法与用途

类别：有毒物质

毒性分级：中毒

急性毒性：腹腔-小鼠 LD50: 750 毫克/公斤

可燃性危险特性：热分解排出有毒氮氧化物烟雾

储运特性：库房低温通风干燥

灭火剂：水、二氧化碳、干粉、泡沫

反应信息

• 作为产物：
  描述：

  4-胍基苯甲酸盐酸盐 、 水杨酸甲酯 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70%的产率得到2'-甲氧羰基苯基4-胍基苯甲酸酯
  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

• US4423069A
  申请人：——

  公开号：US4423069A

  公开（公告）日：1983-12-27
• Synthesis and inhibition of human acrosin and trypsin and acute toxicity of aryl 4-guanidinobenzoates
  作者：J. M. Kaminski、L. Bauer、S. R. Mack、R. A. Anderson、D. P. Waller、L. J. D. Zaneveld

  DOI：10.1021/jm00154a015

  日期：1986.4

  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.