4-((Aminoiminomethyl)amino)benzoic acid 8-quinolinyl ester hydrochloride | 89022-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-((Aminoiminomethyl)amino)benzoic acid 8-quinolinyl ester hydrochloride
• 英文别名: 8'-Quinolyl 4-guanidinobenzoate hydrochloride；quinolin-1-ium-8-yl 4-(diaminomethylideneamino)benzoate;chloride
• CAS: 89022-10-6
• 化学式: C₁₇H₁₄N₄O₂*ClH
• 分子量: 342.785
• InChiKey: NDYCBIDEOLYARQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-羟基喹啉 以41%的产率得到4-((Aminoiminomethyl)amino)benzoic acid 8-quinolinyl ester hydrochloride
  参考文献：
  名称：

  Contraceptive method

  摘要：

  避孕方法包括在哺乳动物的生殖道中维持4-胍基苯甲酸酯和某些取代酚的浓度，以有效抑制卵子的受精。除了有效抑制受孕所需的酶外，本发明方法中使用的化合物具有低毒性的优点。此外，在动物的生殖道中水解4-胍基苯甲酸酯时可能释放的酚类物质具有低毒性、腐蚀性或刺激性，因此避孕组合物适合长期使用而不会产生不良副作用。

  公开号：

  US04423069A1

文献信息

• 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.
• Contraceptive method
  申请人：University of Illinois Foundation

  公开号：US04423069A1

  公开（公告）日：1983-12-27

  Contraceptive method comprises maintaining in the genital tract of a mammal an ester of 4-guanidinobenzoic acid and certain substituted phenols in a concentration effective to inhibit the fertilization of ova. In addition to effectively inhibiting the enzymes necessary for conception, the compounds used in the method of the invention are advantageous in possessing low toxicity. Further, the phenolic materials which may be liberated on hydrolysis of the 4-guanidinobenzoates in the genital tract of the animal are low in toxic, caustic or irritating properties, so that the contraceptive compositions are suitable for long-term use without adverse side-effects.

  避孕方法包括在哺乳动物的生殖道中维持4-胍基苯甲酸酯和某些取代酚的浓度，以有效抑制卵子的受精。除了有效抑制受孕所需的酶外，本发明方法中使用的化合物具有低毒性的优点。此外，在动物的生殖道中水解4-胍基苯甲酸酯时可能释放的酚类物质具有低毒性、腐蚀性或刺激性，因此避孕组合物适合长期使用而不会产生不良副作用。