5-(2-chlorobenzylidene)-4-thioxo-thiazolidin-2-one | 197515-00-7

• 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: 5-(2-chlorobenzylidene)-4-thioxo-thiazolidin-2-one
• 英文别名: 4-thioxo-5-(2-chlorobenzylidene)thiazolidin-2-one；(5Z)-5-[(2-chlorophenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
• CAS: 197515-00-7
• 化学式: C₁₀H₆ClNOS₂
• 分子量: 255.749
• InChiKey: BTOPTHJGPJTBAT-YVMONPNESA-N

物化性质

• 熔点：
  166-167 °C
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2-chlorobenzylidene)-4-thioxo-thiazolidin-2-one 、 2-溴-4-苯基乙酰苯 在 氢氧化钾 作用下， 反应 20.0h， 以76%的产率得到3-(4-phenylphenacyl)-4-thioxo-5-(2-chlorobenzylidene)thiazolidin-2-one
  参考文献：
  名称：

  Chantegrel; Albuquerque; Guarda, Annales Pharmaceutiques Francaises, 2002, vol. 60, # 6, p. 403 - 409

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯甲醛 、 4-硫代噻唑烷-2-酮 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 5-(2-chlorobenzylidene)-4-thioxo-thiazolidin-2-one
  参考文献：
  名称：

  Chantegrel; Albuquerque; Guarda, Annales Pharmaceutiques Francaises, 2002, vol. 60, # 6, p. 403 - 409

  摘要：

  DOI：

文献信息

• Anticancer thiopyrano[2,3-d][1,3]thiazol-2-ones with norbornane moiety. Synthesis, cytotoxicity, physico-chemical properties, and computational studies
  作者：Roman Lesyk、Borys Zimenkovsky、Dmytro Atamanyuk、Frank Jensen、Katarzyna Kieć-Kononowicz、Andrzej Gzella

  DOI：10.1016/j.bmc.2006.03.053

  日期：2006.8

  A series of novel 9-substituted-3,7-dithia-5-azatetracyclo[9.2.1.0(2,10).O-4,O-8]tetradecen-4(8)-ones-6 have been synthesized by a stereoselective hetero-Diels-Alder reaction of 5-ylidene-4-thioxo-2-thiazolidone derivatives with norbornene-2. All the compounds have been evaluated for antitumor activity in in vitro human tumor cell lines, and 10 of them possessed significant and selective cytotoxicity (MGM logGI(50) similar to -4.17 to -4.98, for individual cell lines logGI(50) up to -8). COMPARE analyses of differential growth inhibition patterns of compounds at the GI(50) level showed high correlations with some of the antitubulin agents. The lipophilicity of the compounds was studied by RP-TLC and found to correlate well with calculated log P values. Docking and structure-activity relationship studies produced seven QSAR models with 2 or 3 variables, with correlation coefficients r(2) > 0.9 and leave-one-out cross-validation correlation coefficients, q(2) > 0.8. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, antimicrobial and cytotoxic activities of some 5-arylidene-4-thioxo-thiazolidine-2-ones
  作者：Frederico L. Gouveia、Renata M.B. de Oliveira、Tatiane B. de Oliveira、Ivanildo M. da Silva、Silene C. do Nascimento、Kêsia X.F.R. de Sena、Julianna F.C. de Albuquerque

  DOI：10.1016/j.ejmech.2008.10.006

  日期：2009.5

  Several 5-arylidene-4-thioxo-thiazolidine-2-ones (3a-n) were synthesized and evaluated as antimicrobial agents against representative strains, including multidrug-resistant strains of clinical isolates. Also, the antiproliferative activity was evaluated against two human carcinoma cell lines (NCI-H292 and HEp-2). The compounds containing the 5-arylidene subunit presented greater antimicrobial activities against Gram positive bacteria, including the multidrug-resistant clinical isolates, than the 4-thioxo-thiazolidine-2-one. Important SAR information was also gathered, such as the contribution of thiocarbonyl attached at 4-position on the thiazolidine heterocyclic for antimicrobial properties. None of the derivatives exhibited significant anti proliferative activity against the human carcinoma cell lines. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Chantegrel; Albuquerque; Guarda, Annales Pharmaceutiques Francaises, 2002, vol. 60, # 6, p. 403 - 409
  作者：Chantegrel、Albuquerque、Guarda、Perrissin、Lima、Galdino、Brandao、Thomasson、Pitta、Luu-Duc

  DOI：——

  日期：——