1-[(1-Methylindole-3-carbonyl)amino]-3-phenylthiourea | 894231-51-7

• 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
• 英文名称: 1-[(1-Methylindole-3-carbonyl)amino]-3-phenylthiourea
• 英文别名: 1-[(1-methylindole-3-carbonyl)amino]-3-phenylthiourea
• CAS: 894231-51-7
• 化学式: C₁₇H₁₆N₄OS
• 分子量: 324.406
• InChiKey: PBRAHDJDURMVNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(1-Methylindole-3-carbonyl)amino]-3-phenylthiourea 在 乙酰氯 作用下， 以75%的产率得到5-(1-methylindol-3-yl)-N-phenyl-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents

  摘要：

  A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v were prepared and studied for their anticancer activity against selected human cancer cell lines. The reaction of indolylhydrazides 3a-h with a variety of aryl isothiocyanates 4 afforded the key intermediate thiosemicarbazides 5a-v, which upon treatment with acetyl chloride produced the 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v in good yields. Most of the synthesized compounds showed selective cytotoxicity towards human breast cancer cell line (MDA-MB-231). Of the synthesized 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles, compound 6f is the most potent towards tested cancer cell lines (IC50 = 0.15-1.18 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.047
• 作为产物：
  描述：

  ethyl 1-methyl-1H-indole-3-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 1-[(1-Methylindole-3-carbonyl)amino]-3-phenylthiourea
  参考文献：
  名称：

  A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents

  摘要：

  A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v were prepared and studied for their anticancer activity against selected human cancer cell lines. The reaction of indolylhydrazides 3a-h with a variety of aryl isothiocyanates 4 afforded the key intermediate thiosemicarbazides 5a-v, which upon treatment with acetyl chloride produced the 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v in good yields. Most of the synthesized compounds showed selective cytotoxicity towards human breast cancer cell line (MDA-MB-231). Of the synthesized 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles, compound 6f is the most potent towards tested cancer cell lines (IC50 = 0.15-1.18 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.047

文献信息

• Electrochemical Synthesis of N-Substituted 5-(1H-Indol-3-yl)-1,3,4-oxadiazole-2-amines: A Mild and Green Approach
  作者：Tarun M. Patel、Khushbu G. Patel、Parasar Modh

  DOI：10.1134/s1070363223110403

  日期：2023.11