| 1400584-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1400584-12-4
• 化学式: C₂₀H₁₉ClN₂OS
• 分子量: 370.903
• InChiKey: ABCHDNIRQCIPSM-JLZFKDTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.67
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-(2-甲基丙基)-N'-苯基硫脲 在 哌啶 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis, characterization and structure optimization of a series of thiazolidinone derivatives as Entamoeba histolytica inhibitors

  摘要：

  A series of thiazolidinone derivatives were synthesized by sodium acetate assisted cyclization of 1-isobutyl-3-phenylthiourea with chloroacetic acid followed by the piperidine facilitated substitution of the resulting thiazolidinone with different substituted aldehydes. The ethene and imine double bonds adopt (Z,Z) configuration as indicated by H-1-H-1 COSY and 2D-NOESY H-1 NMR and further confirmed by the crystal structure studies. The in vitro antiamoebic activity of these compounds was evaluated against HM1:IMSS strain of Entamoeba histolytica. Eight compounds exhibited promising activity with IC50 values (0.11-0.172 mu M) lower than the standard drug metronidazole (IC50 1.64 mu M). In vitro cytotoxicity results revealed low cytotoxic up to the concentration of 25 mu M. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.052

文献信息

• Molecular structure and biological activities of 4-thiazolidinone derivatives: a combined theoretical and experimental study
  作者：Md. Mushtaque、Fernando Avecilla、Abdulmohsen Khalaf Dhahi Alsukaibi、Subash S. Pingale、Kirtee M. Kamble、M. Moshahid A. Rizvi

  DOI：10.1080/10426507.2022.2134371

  日期：2023.2.1

  Abstract In this study, we report the structural and biological characterization of (2Z,5Z)-5-(4-methyl benzylidene)-3-(2-methylpropyl)-2-(phenylimino)-1,3-thiazolin-4-one (6a) and (2Z,5Z)-5-(3-chlorobenzylidene)-3-(2-methylpropyl)-2-(phenylimino)-1,3-thiazolin-4-one (6b). These compounds were synthesized following the reported method and the molecular structures were confirmed by single-crystal X-ray

  摘要 在这项研究中，我们报告了 (2 Z ,5Z)-5-(4-甲基亚苄基)-3-(2-甲基丙基)-2-(苯基亚氨基)-1,3-噻唑啉-4-的结构和生物学特性一个 ( 6a ) 和 (2 Z ,5 Z )-5-(3-chlorobenzylidene)-3-(2-methylpropyl)-2-(phenylimino)-1,3-thiazolin-4-one ( 6b )。这些化合物是按照报道的方法合成的，分子结构通过单晶 X 射线衍射研究得到证实。进行密度泛函理论（DFT）计算以补充结构和光谱特征。体外使用 MTT 测定法测试化合物对癌性（SW-480 和 MCF-7）和正常（HEK-293）细胞系的细胞毒性。结果表明，化合物的环外亚甲基质子和环外氮均采用(Z,Z)-构型。据观察，化合物6a（对 SW-480 的IC 50 = 190 ± 0.23 μg/mL，对 MCF-7 的 IC 50
• Synthesis, characterization and structure optimization of a series of thiazolidinone derivatives as Entamoeba histolytica inhibitors
  作者：Md. Mushtaque、Fernando Avecilla、Amir Azam

  DOI：10.1016/j.ejmech.2012.06.052

  日期：2012.9

  A series of thiazolidinone derivatives were synthesized by sodium acetate assisted cyclization of 1-isobutyl-3-phenylthiourea with chloroacetic acid followed by the piperidine facilitated substitution of the resulting thiazolidinone with different substituted aldehydes. The ethene and imine double bonds adopt (Z,Z) configuration as indicated by H-1-H-1 COSY and 2D-NOESY H-1 NMR and further confirmed by the crystal structure studies. The in vitro antiamoebic activity of these compounds was evaluated against HM1:IMSS strain of Entamoeba histolytica. Eight compounds exhibited promising activity with IC50 values (0.11-0.172 mu M) lower than the standard drug metronidazole (IC50 1.64 mu M). In vitro cytotoxicity results revealed low cytotoxic up to the concentration of 25 mu M. (C) 2012 Elsevier Masson SAS. All rights reserved.