5-acetyl-3-(4-anisyl)-2-(4-(2,3-dimethyl-1-phenyl-5-oxo-pyrazol-4-yl)thiazol-2-ylimino)-1,3,4-thiadiazole | 1519975-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-acetyl-3-(4-anisyl)-2-(4-(2,3-dimethyl-1-phenyl-5-oxo-pyrazol-4-yl)thiazol-2-ylimino)-1,3,4-thiadiazole
• 英文别名: 4-[2-[[5-Acetyl-3-(4-methoxyphenyl)-1,3,4-thiadiazol-2-ylidene]amino]-1,3-thiazol-4-yl]-1,5-dimethyl-2-phenylpyrazol-3-one；4-[2-[[5-acetyl-3-(4-methoxyphenyl)-1,3,4-thiadiazol-2-ylidene]amino]-1,3-thiazol-4-yl]-1,5-dimethyl-2-phenylpyrazol-3-one
• CAS: 1519975-27-9
• 化学式: C₂₅H₂₂N₆O₃S₂
• 分子量: 518.62
• InChiKey: SCGSRYXFALNFCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  96.3
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  2-氨基-4-(1,2-二氢-1,5-二甲基-2-苯基-3-氧代-3H-吡唑-4-基)噻唑 在 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 5-acetyl-3-(4-anisyl)-2-(4-(2,3-dimethyl-1-phenyl-5-oxo-pyrazol-4-yl)thiazol-2-ylimino)-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents

  摘要：

  N-(4-(Pyrazol-4-yl)thiazol-2-y1)-N'-phenylthiourea derivative 2 was synthesized and then treated with variety of hydrazonoyl chlorides under basic condition at reflux to afford the corresponding 2-(4-(pyrazol-4-yl)thiazol-2-ylimino)-1,3,4-thiadiazole derivatives 6, 10a-e and 17a-e. Reaction of 2 with ethyl chloroacetate and with 3-chloro-2,4-pentanedione gave the thiazolidin-4-one 22 and 1,3-thiazole 25 derivatives, respectively. Condensation of thiazolidin-4-one 22 with aldehydes gave their 5-arylidene derivatives 23a-f. Most of the synthesized compounds were tested for anticancer activity against human hepatocelluar carcinoma HepG2, human breast cancer MCF-7 and human lung cancer A549. Their SAR was studied and variously affected by the electronic factor of electron donating and withdrawing groups. Many of the tested compounds showed moderate to high anticancer activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.042