N-(4-acetyl-5-(2-chloro-7-methylquinolin-3-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)-acetamide | 1266333-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(4-acetyl-5-(2-chloro-7-methylquinolin-3-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)-acetamide
• 英文别名: N-[3-acetyl-2-(2-chloro-7-methylquinolin-3-yl)-2H-1,3,4-thiadiazol-5-yl]acetamide
• CAS: 1266333-03-2
• 化学式: C₁₆H₁₅ClN₄O₂S
• 分子量: 362.84
• InChiKey: HVMNZFLPJJLELS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-acetyl-5-(2-chloro-7-methylquinolin-3-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)-acetamide 在 sodium azide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 以70%的产率得到N-(4-acetyl-4,5-dihydro-5-(8-methyl-tetrazolo[1,5-a]quinolin-4-yl)-1,3,4-thiadiazol-2-yl)acetamide
  参考文献：
  名称：

  Facile synthesis of novel quinoline derivatives as anticancer agents

  摘要：

  Convenient and efficient synthesis of novel N-(4-acetyl-4,5-dihydro-5-(7,8,9-substituted-tetrazolo[1,5-a]-quinolin-4-yl)-1,3,4-thiadiazol-2-yl)acetamides 4a-j and their in vitro anticancer activity against two cell lines viz., human breast cancer cell line MCF7 and human cervix cancer cell line HeLa were carried out. GI50, LC50, TGI values were evaluated. Two of the compounds 4e and 4i with halogen substituent at 7th position of the target molecules have shown potent activity against human cervix cancer cell line HeLa. DNA cleavage studies revealed that most of these compounds show partial cleavage and few of them show complete cleavage of DNA.

  DOI：

  10.1007/s00044-013-0855-2
• 作为产物：
  描述：

  2-氯-7-甲基-3-喹啉甲醛 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 N-(4-acetyl-5-(2-chloro-7-methylquinolin-3-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)-acetamide
  参考文献：
  名称：

  An efficient one-pot cyclization of quinoline thiosemicarbazones to quinolines derivatized with 1,3,4-thiadiazole as anticancer and anti-tubercular agents

  摘要：

  A series of 6,7,8-substituted thiosemicarbazones (2a-j) of 2-chloro-3-formyl-quinoline derivatives were cyclized to the title compounds (3a-j) using acetic anhydride. The structures of the final compounds (3a-j) were confirmed by elemental and spectral (IR, H-1 NMR and MS) analysis. Some of the title compounds have shown promising anticancer and antitubercular activities.

  DOI：

  10.1007/s00044-010-9522-z