Ethyl 1-oxo-2,3-dihydro-1H-indene-4-carbimidothioate | 138764-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: Ethyl 1-oxo-2,3-dihydro-1H-indene-4-carbimidothioate
• 英文别名: ethyl 1-oxo-2,3-dihydroindene-4-carboximidothioate
• CAS: 138764-35-9
• 化学式: C₁₂H₁₃NOS
• 分子量: 219.307
• InChiKey: XUVBAGQQIUMTMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 1-oxo-2,3-dihydro-1H-indene-4-carbimidothioate 在 盐酸 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 40.0h， 生成 2-(4-aminoiminomethyl)-2,3-dihydro-1H-inden-1-ylidene dihydrochloride
  参考文献：
  名称：

  4-Amidinoindan-1-one 2'-amidinohydrazone: a new potent and selective inhibitor of S-adenosylmethionine decarboxylase

  摘要：

  Two isomeric amidino-2-acetylpyridine amidinohydrazones, 11 and 12, and 4-amidinoindanone amidinohydrazone, 17, have been synthesized and tested for inhibition of S-adenosylmethionine decarboxylase (SAMDC) and diamine oxidase and for antiproliferative activity against T24 human bladder carcinoma cells. Compound 11 inhibited SAMDC with an IC50 of 10 nM and was 140- and >500-fold more potent than methylglyoxal bis(guanylhydrazone) (MGBG) and 12, respectively. The difference in potency between 11 and 12 was interpreted with the help of molecular modeling and appeared to be associated with two different low-energy conformations of the compounds. Compound 17 which represents a conformationally constrained analogue of 11, was superior to the latter and MGBG with respect to selective inhibition of SAMDC and antiproliferative activity, and is of interest as a potential anticancer agent and a drug for the treatment of protozoal and Pneumocystis carinii infections.

  DOI：

  10.1021/jm00067a014
• 作为产物：
  描述：

  2,3-二氢-1-氧代-1H-茚-4-甲腈 在 吡啶 、 硫化氢 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 35.0h， 生成 Ethyl 1-oxo-2,3-dihydro-1H-indene-4-carbimidothioate
  参考文献：
  名称：

  4-Amidinoindan-1-one 2'-amidinohydrazone: a new potent and selective inhibitor of S-adenosylmethionine decarboxylase

  摘要：

  Two isomeric amidino-2-acetylpyridine amidinohydrazones, 11 and 12, and 4-amidinoindanone amidinohydrazone, 17, have been synthesized and tested for inhibition of S-adenosylmethionine decarboxylase (SAMDC) and diamine oxidase and for antiproliferative activity against T24 human bladder carcinoma cells. Compound 11 inhibited SAMDC with an IC50 of 10 nM and was 140- and >500-fold more potent than methylglyoxal bis(guanylhydrazone) (MGBG) and 12, respectively. The difference in potency between 11 and 12 was interpreted with the help of molecular modeling and appeared to be associated with two different low-energy conformations of the compounds. Compound 17 which represents a conformationally constrained analogue of 11, was superior to the latter and MGBG with respect to selective inhibition of SAMDC and antiproliferative activity, and is of interest as a potential anticancer agent and a drug for the treatment of protozoal and Pneumocystis carinii infections.

  DOI：

  10.1021/jm00067a014

文献信息

• J. Med. Chem. 1993, 36, 2168-2171
  作者：

  DOI：——

  日期：——