2-(5-(naphthalen-1-yl)-3-phenyl-4, 5-dihydro-1 H-pyrazol-1-yl) thiazol-4(5H)-one | 1599445-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(5-(naphthalen-1-yl)-3-phenyl-4, 5-dihydro-1 H-pyrazol-1-yl) thiazol-4(5H)-one
• 英文别名: 2-(3-Naphthalen-1-yl-5-phenyl-3,4-dihydropyrazol-2-yl)-1,3-thiazol-4-one；2-(3-naphthalen-1-yl-5-phenyl-3,4-dihydropyrazol-2-yl)-1,3-thiazol-4-one
• CAS: 1599445-08-5
• 化学式: C₂₂H₁₇N₃OS
• 分子量: 371.462
• InChiKey: ZDKAJODZVYYAAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  70.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(naphthalen-1-yl)-1-phenylprop-2-en-1-one 在 sodium acetate 、 乙酸酐 、 potassium hydroxide 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 2-(5-(naphthalen-1-yl)-3-phenyl-4, 5-dihydro-1 H-pyrazol-1-yl) thiazol-4(5H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents

  摘要：

  A series of compounds which contain pyrazole, thiazole and naphthalene ring (1a-7a, 1b-7b, 1c-7c, 1d-7d) were firstly synthesized and their anti-proliferative activity, EGFR inhibitory activity, cytotoxicity and inhibition to Hela cell migration were evaluated. Compound 2-(3-(3,4-dimethylphenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl) thiazol-4(5H)-one (7d) displayed the most potent inhibitory activity (IC50 = 0.86 mu M for Hela and IC50 = 0.12 mu M for EGFR). Structure-activity relationship (SAR) analysis showed that the anti-proliferative activity was affected by A-ring-substituent (-OCH3 > -CH3 > -H > -Br > -Cl > -F). Docking simulation of compound 7d into EGFR active site showed that naphthalene ring of 7d with LYS721 formed two p-pi bonds, which enhanced antitumor activity. Therefore, compound 7d may be developed as a potential antitumor agent. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.072

文献信息

• Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents
  作者：Ji-Wen Yuan、She-Feng Wang、Zhong-Liang Luo、Han-Yue Qiu、Peng-Fei Wang、Xin Zhang、Yong-An Yang、Yong Yin、Fei Zhang、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2014.03.072

  日期：2014.5

  A series of compounds which contain pyrazole, thiazole and naphthalene ring (1a-7a, 1b-7b, 1c-7c, 1d-7d) were firstly synthesized and their anti-proliferative activity, EGFR inhibitory activity, cytotoxicity and inhibition to Hela cell migration were evaluated. Compound 2-(3-(3,4-dimethylphenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl) thiazol-4(5H)-one (7d) displayed the most potent inhibitory activity (IC50 = 0.86 mu M for Hela and IC50 = 0.12 mu M for EGFR). Structure-activity relationship (SAR) analysis showed that the anti-proliferative activity was affected by A-ring-substituent (-OCH3 > -CH3 > -H > -Br > -Cl > -F). Docking simulation of compound 7d into EGFR active site showed that naphthalene ring of 7d with LYS721 formed two p-pi bonds, which enhanced antitumor activity. Therefore, compound 7d may be developed as a potential antitumor agent. (C) 2014 Elsevier Ltd. All rights reserved.