(Z)-5-(((Z)-9-chloro-6,7-dihydro-5H-benzo[7]annulen-8-yl)methylene)thiazolidine-2,4-dione | 1558039-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-5-(((Z)-9-chloro-6,7-dihydro-5H-benzo[7]annulen-8-yl)methylene)thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[(5-chloro-8,9-dihydro-7H-benzo[7]annulen-6-yl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1558039-23-8
• 化学式: C₁₅H₁₂ClNO₂S
• 分子量: 305.785
• InChiKey: GVMDTOFZNFIJMT-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-(((Z)-9-chloro-6,7-dihydro-5H-benzo[7]annulen-8-yl)methylene)thiazolidine-2,4-dione 、 2-溴苯乙酮 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (Z)-5-((9-chloro-6,7-dihydro-5H-benzo[7]annulen-8-yl)methylene)-3-(2-oxo-2-phenylethyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Studies on the synthetic and structural aspects of benzosuberones bearing 2, 4-thiazolidenone moiety as potential anti-cancer agents

  摘要：

  Novel representative of the important group of biologically active benzosuberones bearing 2, 4-thiazolidenone moiety was synthesized as potential anticancer agents (6a-j). These compounds were synthesized in good yields from Knoevenagel condensation of compounds 2a-b with thiazolidenone derivatives 3a-e in the presence of sodium acetate and glacial acetic acid. The in vitro cytotoxicity of these compounds was evaluated against different human cancer cell lines (A549, HeLa, MDA-MB-231, MCF-7) and normal cell line, HEK293. Compound 6a exhibited promising cytotoxicity with IC50 values ranging from 2.98 to 13.34 mu M against all the tested cancer cell lines, Hela, A549, MCF-7 and MDA-MB-231, while compound 6g showed potent cytotoxicity against human breast adenocarcinoma cell line (MCF-7, IC50 value of 1.91 mu M). (C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.10.078
• 作为产物：
  描述：

  1-苯并环庚酮 在 sodium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 以 溶剂黄146 为溶剂， 反应 15.25h， 生成 (Z)-5-(((Z)-9-chloro-6,7-dihydro-5H-benzo[7]annulen-8-yl)methylene)thiazolidine-2,4-dione
  参考文献：
  名称：

  Studies on the synthetic and structural aspects of benzosuberones bearing 2, 4-thiazolidenone moiety as potential anti-cancer agents

  摘要：

  Novel representative of the important group of biologically active benzosuberones bearing 2, 4-thiazolidenone moiety was synthesized as potential anticancer agents (6a-j). These compounds were synthesized in good yields from Knoevenagel condensation of compounds 2a-b with thiazolidenone derivatives 3a-e in the presence of sodium acetate and glacial acetic acid. The in vitro cytotoxicity of these compounds was evaluated against different human cancer cell lines (A549, HeLa, MDA-MB-231, MCF-7) and normal cell line, HEK293. Compound 6a exhibited promising cytotoxicity with IC50 values ranging from 2.98 to 13.34 mu M against all the tested cancer cell lines, Hela, A549, MCF-7 and MDA-MB-231, while compound 6g showed potent cytotoxicity against human breast adenocarcinoma cell line (MCF-7, IC50 value of 1.91 mu M). (C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.10.078

文献信息

• Studies on the synthetic and structural aspects of benzosuberones bearing 2, 4-thiazolidenone moiety as potential anti-cancer agents
  作者：Lingaiah Nagarapu、Bandi Yadagiri、Rajashaker Bantu、C. Ganesh Kumar、Sujitha Pombala、Jagadesh Nanubolu

  DOI：10.1016/j.ejmech.2013.10.078

  日期：2014.1

  Novel representative of the important group of biologically active benzosuberones bearing 2, 4-thiazolidenone moiety was synthesized as potential anticancer agents (6a-j). These compounds were synthesized in good yields from Knoevenagel condensation of compounds 2a-b with thiazolidenone derivatives 3a-e in the presence of sodium acetate and glacial acetic acid. The in vitro cytotoxicity of these compounds was evaluated against different human cancer cell lines (A549, HeLa, MDA-MB-231, MCF-7) and normal cell line, HEK293. Compound 6a exhibited promising cytotoxicity with IC50 values ranging from 2.98 to 13.34 mu M against all the tested cancer cell lines, Hela, A549, MCF-7 and MDA-MB-231, while compound 6g showed potent cytotoxicity against human breast adenocarcinoma cell line (MCF-7, IC50 value of 1.91 mu M). (C) 2013 Published by Elsevier Masson SAS.