4-Guanidino benzoic acid 4-t-butylphenyl ester | 99966-55-9

• 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
• 英文名称: 4-Guanidino benzoic acid 4-t-butylphenyl ester
• 英文别名: (4-tert-butylphenyl) 4-(diaminomethylideneamino)benzoate
• CAS: 99966-55-9
• 化学式: C₁₈H₂₁N₃O₂
• 分子量: 311.384
• InChiKey: QKIICUBVSHYYQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  90.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-叔丁基苯酚 、 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58%的产率得到4-Guanidino benzoic acid 4-t-butylphenyl ester
  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

• CURABLE COMPOSITION
  申请人：Kaneka Corporation

  公开号：EP1990371A1

  公开（公告）日：2008-11-12

  The present invention has its object to provide a curable composition which comprises a reactive silyl group-containing organic polymer, does not contain, as a silanol condensation catalyst, any organotin type curing catalyst currently of concern because of the toxic feature thereof, is excellent in surface curability and depth curability and, further, can provide cured products excellent in adhesiveness; the above obj ect can be achieved by a curable composition which comprises: an organic polymer (A) containing a silicon-containing group capable of crosslinking under siloxane bond formation; and a guanidine compound (B-1), as a silanol condensation catalyst (B), represented by the general formula (1):         R1N=C(NR12)2     (1) (wherein one of the five R1s is an aryl group and the other four R1s each independently is a hydrogen atom or a hydrocarbon group in which the carbon atom at position 1 is saturated).

  本发明的目的是提供一种可固化组合物，该组合物包括含活性硅烷基团的有机聚合物，作为硅烷醇缩合催化剂，不含任何目前因其毒性特征而受到关注的有机锡类固化催化剂，具有优异的表面固化性和深度固化性，而且，可提供具有优异粘合性的固化产品；上述目的可通过一种可固化组合物来实现，该组合物包括：含硅烷基团的有机聚合物(A)；作为硅烷醇缩合催化剂(B)的胍化合物(B-1)：一种有机聚合物 (A)，其中含有能在硅氧烷键形成下交联的含硅基团；和一种胍化合物 (B-1)，作为硅醇缩合催化剂 (B)，由通式 (1) 表示： R1N=C(NR12)2 (1) (其中五个 R1s 中的一个为芳基，另外四个 R1s 分别独立地为氢原子或碳原子位于第 1 位为饱和的烃基）。
• US7960459B2
  申请人：——

  公开号：US7960459B2

  公开（公告）日：2011-06-14
• 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.