1-[(6-methoxy-1H-indole-3-carbonyl)amino]-3-(4-methoxyphenyl)thiourea | 1396744-22-1

• 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-[(6-methoxy-1H-indole-3-carbonyl)amino]-3-(4-methoxyphenyl)thiourea
• CAS: 1396744-22-1
• 化学式: C₁₈H₁₈N₄O₃S
• 分子量: 370.432
• InChiKey: CCWCTBWHZWTXRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(6-methoxy-1H-indole-3-carbonyl)amino]-3-(4-methoxyphenyl)thiourea 在 乙酰氯 作用下， 以55%的产率得到5-(6-methoxy-1H-indol-3-yl)-N-(4-methoxyphenyl)-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 6-methoxyindole-3-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-[(6-methoxy-1H-indole-3-carbonyl)amino]-3-(4-methoxyphenyl)thiourea
  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