(Z)-5-(acridin-9-ylmethylene)-3-(4-chlorobenzyl)thiazolidine-2,4-dione | 675868-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (Z)-5-(acridin-9-ylmethylene)-3-(4-chlorobenzyl)thiazolidine-2,4-dione
• 英文别名: (5Z)-5-(acridin-9-ylmethylidene)-3-[(4-chlorophenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 675868-74-3
• 化学式: C₂₄H₁₅ClN₂O₂S
• 分子量: 430.914
• InChiKey: GMCUOUPIWVXCTM-XKZIYDEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  75.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[(4-氯苯基)甲基]-1,3-噻唑烷-2,4-二酮 、 9-[ethyl (2-cyano)-acrylate]-acridine 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以51%的产率得到(Z)-5-(acridin-9-ylmethylene)-3-(4-chlorobenzyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and cytotoxic activity of new acridine-thiazolidine derivatives

  摘要：

  Although their exact role in controlling tumour growth and apoptosis in humans remains undefined, acridine and thiazolidine compounds have been shown to act as tumour suppressors in most cancers. Based on this finding, a series of novel hybrid 5-acridin-9-ylmethylene-3-benzyl-thiazolidine-2,4-diones were synthesised via N-alkylation and Michael reaction. The cell viability was analysed using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, and DNA interaction assays were performed using electrochemical techniques. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.007

文献信息

• [EN] MOLECULES WITH ANTITUMOR ACTIVITY AND CHEMICAL SYNTHESIS<br/>[FR] MOLECULES A ACTIVITE ANTITUMORALE, ET PROCEDE DE SYNTHESE CHIMIQUE
  申请人：CONSELHO NACIONAL CNPQ

  公开号：WO2004024058A2

  公开（公告）日：2004-03-25

  Synthesis and structure of news acridine-thiazolidine-thiazacridine and acridine-imidaziolidine-imidazacridine compounds with antitumor activity and their therapeutic use as anticancer agents.
• Synthesis and cytotoxic activity of new acridine-thiazolidine derivatives
  作者：Francisco W.A. Barros、Teresinha Gonçalves Silva、Marina Galdino da Rocha Pitta、Daniel P. Bezerra、Letícia V. Costa-Lotufo、Manoel Odorico de Moraes、Cláudia Pessoa、Maria Aline F.B. de Moura、Fabiane C. de Abreu、Maria do Carmo Alves de Lima、Suely Lins Galdino、Ivan da Rocha Pitta、Marilia O.F. Goulart

  DOI：10.1016/j.bmc.2012.04.007

  日期：2012.6

  Although their exact role in controlling tumour growth and apoptosis in humans remains undefined, acridine and thiazolidine compounds have been shown to act as tumour suppressors in most cancers. Based on this finding, a series of novel hybrid 5-acridin-9-ylmethylene-3-benzyl-thiazolidine-2,4-diones were synthesised via N-alkylation and Michael reaction. The cell viability was analysed using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, and DNA interaction assays were performed using electrochemical techniques. (C) 2012 Elsevier Ltd. All rights reserved.