2-(2-(3,5-dichloro-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one | 416884-13-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-(3,5-dichloro-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one
• 英文别名: (2E)-2-[(3,5-dichloro-2-hydroxyphenyl)methylidenehydrazinylidene]-1,3-thiazolidin-4-one
• CAS: 416884-13-4
• 化学式: C₁₀H₇Cl₂N₃O₂S
• 分子量: 304.156
• InChiKey: BBFZNAMYBDLSGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-dichlorosalicylaldehyde thiosemicarbazone 、 溴乙酸乙酯 在 sodium acetate 作用下， 以 乙醇 为溶剂， 以77%的产率得到2-(2-(3,5-dichloro-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 kinase inhibitors

  摘要：

  Two series of thiazolidinone derivatives designing for potential EGFR and HER-2 kinase inhibitors have been discovered. Some of them exhibited significant EGFR and HER-2 inhibitory activity. Compound 2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one (12) displayed the most potent inhibitory activity (IC50 = 0.09 mu M for EGFR and IC50 = 0.42 mu M for HER-2), comparable to the positive control erlotinib. Docking simulation was performed to position compound 12 into the EGFR active site to determine the probable binding model. Antiproliferative assay results indicating that some of the thiazolidinone derivatives own high antiproliferative activity against MCF-7. Compound 12 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.051

文献信息

• Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 kinase inhibitors
  作者：Peng-Cheng Lv、Chang-Fang Zhou、Jin Chen、Peng-Gang Liu、Kai-Rui Wang、Wen-Jun Mao、Huan-Qiu Li、Ying Yang、Jing Xiong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2009.10.051

  日期：2010.1

  Two series of thiazolidinone derivatives designing for potential EGFR and HER-2 kinase inhibitors have been discovered. Some of them exhibited significant EGFR and HER-2 inhibitory activity. Compound 2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one (12) displayed the most potent inhibitory activity (IC50 = 0.09 mu M for EGFR and IC50 = 0.42 mu M for HER-2), comparable to the positive control erlotinib. Docking simulation was performed to position compound 12 into the EGFR active site to determine the probable binding model. Antiproliferative assay results indicating that some of the thiazolidinone derivatives own high antiproliferative activity against MCF-7. Compound 12 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent. (C) 2009 Elsevier Ltd. All rights reserved.