2-(2-(1H-indol-3-yl)acetyl)-N-(4-methoxyphenyl)hydrazinecarbothioamide | 1024522-99-3

• 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: 2-(2-(1H-indol-3-yl)acetyl)-N-(4-methoxyphenyl)hydrazinecarbothioamide
• 英文别名: 1-[[2-(1H-indol-3-yl)acetyl]amino]-3-(4-methoxyphenyl)thiourea
• CAS: 1024522-99-3
• 化学式: C₁₈H₁₈N₄O₂S
• 分子量: 354.433
• InChiKey: PNLHBEAFOAYELH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 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：
  110
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-(1H-indol-3-yl)acetyl)-N-(4-methoxyphenyl)hydrazinecarbothioamide 在 乙酰氯 作用下， 以65%的产率得到5-(1H-indol-3-ylmethyl)-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：

  吲哚-3-醋酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(2-(1H-indol-3-yl)acetyl)-N-(4-methoxyphenyl)hydrazinecarbothioamide
  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

• A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents
  作者：Dalip Kumar、N. Maruthi Kumar、Brett Noel、Kavita Shah

  DOI：10.1016/j.ejmech.2012.06.047

  日期：2012.9

  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.
• Tryptophan and thiosemicarbazide derivatives: design, synthesis, and biological evaluation as potential β-d-galactosidase and β-d-glucosidase inhibitors
  作者：Reema Abu Khalaf、Ahmed Mutanabbi Abdula、Mohammad S. Mubarak、Mutasem O. Taha

  DOI：10.1007/s00044-014-1314-4

  日期：2015.6

  Glycosidases, including beta-d-galactosidase and beta-d-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several beta-d-galactosidase and beta-d-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as beta-d-galactosidase and beta-d-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 A mu M) and 4d (49 % inhibition at 100 A mu M) exhibited the best inhibitory bioactivities against beta-d-galactosidase and beta-d-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.