2-(3-methoxy-4-hydroxyphenyl)-5-(4-nitrophenylamino)-1,3,4-thiadiazole | 1300713-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(3-methoxy-4-hydroxyphenyl)-5-(4-nitrophenylamino)-1,3,4-thiadiazole
• 英文别名: 2-Methoxy-4-[5-(4-nitroanilino)-1,3,4-thiadiazol-2-yl]phenol；2-methoxy-4-[5-(4-nitroanilino)-1,3,4-thiadiazol-2-yl]phenol
• CAS: 1300713-17-0
• 化学式: C₁₅H₁₂N₄O₄S
• 分子量: 344.351
• InChiKey: XTKVLKWRQGBCKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 ammonium iron(III) sulfate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-(3-methoxy-4-hydroxyphenyl)-5-(4-nitrophenylamino)-1,3,4-thiadiazole
  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

文献信息

• One-pot synthesis and anticancer studies of 2-arylamino-5-aryl-1,3,4-thiadiazoles
  作者：Dalip Kumar、Buchi Reddy Vaddula、Kuei-Hua Chang、Kavita Shah

  DOI：10.1016/j.bmcl.2011.02.083

  日期：2011.4

  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.