N-[1-(4-methoxybenzyl)-1H-indol-3-ylcarbonyl]-N''-4-methoxyphenylthiosemicarbazide | 1396744-16-3

• 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: N-[1-(4-methoxybenzyl)-1H-indol-3-ylcarbonyl]-N''-4-methoxyphenylthiosemicarbazide
• 英文别名: 1-(4-Methoxyphenyl)-3-[[1-[(4-methoxyphenyl)methyl]indole-3-carbonyl]amino]thiourea
• CAS: 1396744-16-3
• 化学式: C₂₅H₂₄N₄O₃S
• 分子量: 460.557
• InChiKey: NRRLOZRABFSMGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[1-(4-methoxybenzyl)-1H-indol-3-ylcarbonyl]-N''-4-methoxyphenylthiosemicarbazide 在 乙酰氯 作用下， 以55%的产率得到N-(4-methoxyphenyl)-5-[1-[(4-methoxyphenyl)methyl]indol-3-yl]-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：

  吲哚-3-甲酸乙酯 在 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.25h， 生成 N-[1-(4-methoxybenzyl)-1H-indol-3-ylcarbonyl]-N''-4-methoxyphenylthiosemicarbazide
  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

• Synthesis of New PMB-Substituted Indoles Containing 1,3,4-Oxadiazole and 1,2,4-Triazole Units
  作者：Abdel-Rahman Farghaly、Norbert Haider、Duck-Hyung Lee

  DOI：10.1002/jhet.864

  日期：2012.7

  A series of new indolyl‐1,3,4‐oxadiazole derivatives 3, 4, 5, 6, 7 and 10, indolyl‐1,2,4‐triazole derivatives 14 and 15 was prepared, using 1‐(4‐methoxybenzyl)‐1H‐indole‐3‐carbohydrazide (2) as a key intermediate. Some of the new compounds were evaluated for their antineoplastic activity.

  一系列新的吲哚基1,3,4-恶二唑衍生物的3，4，5，6，7和10，吲哚基-1,2,4-三唑衍生物14和15制备，使用1-（4-甲氧基苄基） ‐1 H ‐吲哚-3-碳酰肼（2）作为关键中间体。对一些新化合物的抗肿瘤活性进行了评估。