1-[[2-(2-甲基-1H-吲哚-3-基)乙酰基]氨基]-3-(4-甲基苯基)硫脲 | 54648-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-[[2-(2-甲基-1H-吲哚-3-基)乙酰基]氨基]-3-(4-甲基苯基)硫脲
• 英文名称: 1-(2-methylindolyl-3-acetyl)-4-p-tolylthiosemicarbazide
• 英文别名: 1H-Indole-3-acetic acid, 2-methyl-, 2-(((4-methylphenyl)amino)thioxomethyl)hydrazide；1-[[2-(2-methyl-1H-indol-3-yl)acetyl]amino]-3-(4-methylphenyl)thiourea
• CAS: 54648-92-9
• 化学式: C₁₉H₂₀N₄OS
• 分子量: 352.46
• InChiKey: HZPBBRJUUBLHHI-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C(Solv: ethanol (64-17-5))
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[[2-(2-甲基-1H-吲哚-3-基)乙酰基]氨基]-3-(4-甲基苯基)硫脲 在 sodium hydroxide 作用下， 反应 0.5h， 以84%的产率得到2,4-Dihydro-5-((2-methyl-1H-indol-3-yl)methyl)-4-(4-methylphenyl)-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2,4-triazole

  摘要：

  3-[ (2-Methyl-1H-3-indolyl)methyl]-4-aryl-4, 5-dihydro-1H-1,2,4-triazole-5-thiones 6a-c and their respective N-{5-[ (2-methyl-1H-3-indolyl) methyl] -1,3,4-thiadiazol-2-yl}-N-arylamines 7a,b have been prepared. The antidepressant profile of 6a,c and 7a was studied on mice with respect to that of the analogous 3-(1H-1-indolylmethyl)-4-aryl-4,5-dihydro-1H-1,2,4-triazole-5-thiones 1a-c and the respective N-{5-[ (2-methyl-1H-3-indolyl) methyl ]-1,3,4-thiadiazol-2-yl}-N-arylamines 2a-c, the synthesis and antimicrobial potency of which we have recently reported. Behavioral effects, induced by the members of both series,in conjunction with their activity in some specific tests (forced swim, pentetrazole convulsions) on mice, show that these derivatives cross the blood-brain barrier and could develop an antidepressant activity comparable to that of imipramine. Blood-brain barrier penetration is also supported by the lipophilicity data obtained for all analogs. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00024-x
• 作为产物：
  描述：

  (2-甲基-吲哚-3-基)-乙酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 1-[[2-(2-甲基-1H-吲哚-3-基)乙酰基]氨基]-3-(4-甲基苯基)硫脲
  参考文献：
  名称：

  Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2,4-triazole

  摘要：

  3-[ (2-Methyl-1H-3-indolyl)methyl]-4-aryl-4, 5-dihydro-1H-1,2,4-triazole-5-thiones 6a-c and their respective N-{5-[ (2-methyl-1H-3-indolyl) methyl] -1,3,4-thiadiazol-2-yl}-N-arylamines 7a,b have been prepared. The antidepressant profile of 6a,c and 7a was studied on mice with respect to that of the analogous 3-(1H-1-indolylmethyl)-4-aryl-4,5-dihydro-1H-1,2,4-triazole-5-thiones 1a-c and the respective N-{5-[ (2-methyl-1H-3-indolyl) methyl ]-1,3,4-thiadiazol-2-yl}-N-arylamines 2a-c, the synthesis and antimicrobial potency of which we have recently reported. Behavioral effects, induced by the members of both series,in conjunction with their activity in some specific tests (forced swim, pentetrazole convulsions) on mice, show that these derivatives cross the blood-brain barrier and could develop an antidepressant activity comparable to that of imipramine. Blood-brain barrier penetration is also supported by the lipophilicity data obtained for all analogs. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00024-x

文献信息

• Kadry; Badawy; Hanna, Pharmazie, 1986, vol. 41, # 8, p. 558 - 559
  作者：Kadry、Badawy、Hanna

  DOI：——

  日期：——
• Sengupta, Anil K.; Gupta, Anurag Ateet, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 3, p. 263 - 266
  作者：Sengupta, Anil K.、Gupta, Anurag Ateet

  DOI：——

  日期：——
• SENGUPTA, A.;GUPTA, A. A., INDIAN J. CHEM., 1983, 22, N 3, 263-266
  作者：SENGUPTA, A.、GUPTA, A. A.

  DOI：——

  日期：——
• KADRY AZZA M.; BADAWY MOHAMED A.; HANNA H. R., PHARMAZIE, 41,(1986) N 8, 558-559
  作者：KADRY AZZA M.、 BADAWY MOHAMED A.、 HANNA H. R.

  DOI：——

  日期：——
• Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2,4-triazole
  作者：Athanasia Varvaresou、Theodora Siatra-Papastaikoudi、Andrew Tsotinis、Anna Tsantili-Kakoulidou、Alexandre Vamvakides

  DOI：10.1016/s0014-827x(98)00024-x

  日期：1998.5

  3-[ (2-Methyl-1H-3-indolyl)methyl]-4-aryl-4, 5-dihydro-1H-1,2,4-triazole-5-thiones 6a-c and their respective N-5-[ (2-methyl-1H-3-indolyl) methyl] -1,3,4-thiadiazol-2-yl}-N-arylamines 7a,b have been prepared. The antidepressant profile of 6a,c and 7a was studied on mice with respect to that of the analogous 3-(1H-1-indolylmethyl)-4-aryl-4,5-dihydro-1H-1,2,4-triazole-5-thiones 1a-c and the respective N-5-[ (2-methyl-1H-3-indolyl) methyl ]-1,3,4-thiadiazol-2-yl}-N-arylamines 2a-c, the synthesis and antimicrobial potency of which we have recently reported. Behavioral effects, induced by the members of both series,in conjunction with their activity in some specific tests (forced swim, pentetrazole convulsions) on mice, show that these derivatives cross the blood-brain barrier and could develop an antidepressant activity comparable to that of imipramine. Blood-brain barrier penetration is also supported by the lipophilicity data obtained for all analogs. (C) 1998 Elsevier Science S.A. All rights reserved.