(Z)-5-((9-chloro-2,3-dimethyl-6,7-dihydro-5H-benzo[7]annulen-8-yl)methylene)-3-(2-(4-chlorophenyl)-2-oxoethyl)thiazolidine-2,4-dione | 1558039-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-5-((9-chloro-2,3-dimethyl-6,7-dihydro-5H-benzo[7]annulen-8-yl)methylene)-3-(2-(4-chlorophenyl)-2-oxoethyl)thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[(5-chloro-2,3-dimethyl-8,9-dihydro-7H-benzo[7]annulen-6-yl)methylidene]-3-[2-(4-chlorophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione
• CAS: 1558039-21-6
• 化学式: C₂₅H₂₁Cl₂NO₃S
• 分子量: 486.419
• InChiKey: LJBMTEDZYGCQKE-UUYOSTAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二甲基-6,7,8,9-四氢苯并[7]轮烯-5-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-((9-chloro-2,3-dimethyl-6,7-dihydro-5H-benzo[7]annulen-8-yl)methylene)-3-(2-(4-chlorophenyl)-2-oxoethyl)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.