N-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine | 1258974-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine
• CAS: 1258974-13-8
• 化学式: C₁₈H₁₉N₃O₃S
• 分子量: 357.433
• InChiKey: NOKKFEOBEYABLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(p-tolyl)-2-(3,4,5-trimethoxybenzylidene)hydrazine carbothioamide 在 ammonium iron(III) sulfate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  One-pot synthesis and anticancer studies of 2-arylamino-5-aryl-1,3,4-thiadiazoles

  摘要：

  A series of 2-arylamino-5-aryl-1,3,4-thiadiazoles 1a-j were synthesized and screened for their anticancer activity against various human cancer cell lines. The novel one-pot synthesis of 1,3,4-thiadiazoles was achieved by refluxing aryl aldehydes, hydrazine hydrate, and aryl isothiocyanates in methanol followed by oxidative cyclization with ferric ammonium sulfate. The compounds 1g-j with trimethoxyphenyl at the C-5 position displayed extremely potent anticancer activity with at least twofold selectivity (IC(50): 4.3-9.2 mu M). The nature of substituent on the C-2 arylamino ring may be critical in opting for the selectivity towards a particular cancer cell. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.083