(5Z)-5-(3-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one | 23622-20-0

• 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: (5Z)-5-(3-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
• 英文别名: 5-(3-chloro-benzylidene)-2-thioxo-thiazolidin-4-one；5-(3-Chlor-benzyliden)-2-thioxo-thiazolidin-4-on；5-[(3-chlorophenyl)methylene]-2-thioxo-4-thiazolidinone；(5Z)-5-(3-chlorobenzylidene)-2-sulfanyl-1,3-thiazol-4(5H)-one；(5Z)-5-[(3-chlorophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 23622-20-0
• 化学式: C₁₀H₆ClNOS₂
• mdl: MFCD04969009
• 分子量: 255.749
• InChiKey: RUBMOEKDIMPMHT-YVMONPNESA-N

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

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (5Z)-5-(3-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 33.17h， 生成 (Z)-2-(5-(3-chlorobenzyliden)-4-oxo-4,5-dihydrothiazol-2-ylamino)-4-methyl-N-tosylpentanamide
  参考文献：
  名称：

  Structure-based design of rhodanine-based acylsulfonamide derivatives as antagonists of the anti-apoptotic Bcl-2 protein

  摘要：

  A series of novel rhodanine-based acylsulfonamide derivatives were designed, synthesized, and evaluated as small-molecule inhibitors of anti-apoptotic Bcl-2 protein. These compounds exhibit potent antiproliferative activity in three human tumor cell lines (Hep G2, PC-3 and B16-F10). Among them, the most potent compounds 10 and 11 bind to Bcl-2 with a K-i of 20 and 25 nM, respectively. Docking studies demonstrated that these two compounds orient similarly at the binding site of Bcl-2, and the calculated binding affinities (Glide XP score) of compound 10 is more negative than that of compound 11. The binding interactions of compounds with high binding affinity to Bcl-2 protein were analyzed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.079
• 作为产物：
  描述：

  罗丹宁 、 3-氯苯甲醛 在 氨 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以76%的产率得到(5Z)-5-(3-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and Characterization of (Z)-5-Arylmethylidene-rhodanines with Photosynthesis-Inhibiting Properties

  摘要：

  一系列硫代酮衍生物被制备。展示了所有合成化合物的合成方法、分析及光谱数据。通过反相高效液相色谱法（RP-HPLC）分析了所有讨论的硫代酮衍生物的亲脂性。对这些化合物在菠菜（Spinacia oleracea L.）叶 chloroplasts 中抑制光合电子传递（PET）的能力以及在淡水藻类小球藻（Chlorella vulgaris）中降低叶绿素含量进行了测试。讨论了评估化合物的化学结构、物理性质与生物活性之间的构效关系。在大多数测试化合物中，化合物的亲脂性而非R1取代基的电子性质是决定PET抑制活性的关键。最强效的PET抑制剂是(5Z)-5-(4-溴苯甲叉基)-2-硫代-1,3-噻唑烷-4-酮（IC50 = 3.0 μmol/L），而最高的抗藻活性则由(5Z)-5-(4-氯苯甲叉基)-2-硫代-1,3-噻唑烷-4-酮（IC50 = 1.3 μmol/L）表现。

  DOI：

  10.3390/molecules16065207

文献信息

• Synthesis and Characterization of (Z)-5-Arylmethylidene-rhodanines with Photosynthesis-Inhibiting Properties
  作者：Veronika Opletalova、Jan Dolezel、Katarina Kralova、Matus Pesko、Jiri Kunes、Josef Jampilek

  DOI：10.3390/molecules16065207

  日期：——

  A series of rhodanine derivatives was prepared. The synthetic approach, analytical and spectroscopic data of all synthesized compounds are presented. Lipophilicity of all the discussed rhodanine derivatives was analyzed using the RP-HPLC method. The compounds were tested for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts and reduce chlorophyll content in freshwater alga Chlorella vulgaris. Structure-activity relationships between the chemical structure, physical properties and biological activities of the evaluated compounds are discussed. For majority of the tested compounds the lipophilicity of the compound and not electronic properties of the R1 substituent were decisive for PET-inhibiting activity. The most potent PET inhibitor was (5Z)-5-(4-bromobenzylidene)-2-thioxo-1,3-thiazolidin-4-one (IC50 = 3.0 μmol/L) and the highest antialgal activity was exhibited by (5Z)-5-(4-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one (IC50 = 1.3 μmol/L).

  一系列硫代酮衍生物被制备。展示了所有合成化合物的合成方法、分析及光谱数据。通过反相高效液相色谱法（RP-HPLC）分析了所有讨论的硫代酮衍生物的亲脂性。对这些化合物在菠菜（Spinacia oleracea L.）叶 chloroplasts 中抑制光合电子传递（PET）的能力以及在淡水藻类小球藻（Chlorella vulgaris）中降低叶绿素含量进行了测试。讨论了评估化合物的化学结构、物理性质与生物活性之间的构效关系。在大多数测试化合物中，化合物的亲脂性而非R1取代基的电子性质是决定PET抑制活性的关键。最强效的PET抑制剂是(5Z)-5-(4-溴苯甲叉基)-2-硫代-1,3-噻唑烷-4-酮（IC50 = 3.0 μmol/L），而最高的抗藻活性则由(5Z)-5-(4-氯苯甲叉基)-2-硫代-1,3-噻唑烷-4-酮（IC50 = 1.3 μmol/L）表现。
• Thiazolidinone derivatives as hypoglycemic agents and for treating Alzheimer's disease
  申请人：ELI LILLY AND COMPANY

  公开号：EP0587377A2

  公开（公告）日：1994-03-16

  Provided are methods for treating hyperglycemia and Alzheimer's disease utilizing certain rhodanine derivatives. Certain of the rhodanine derivatives utilized in the instant methods are novel and, accordingly, such compounds, process for preparing same and pharmaceutical formulations thereof, are also provided.

  本发明提供了利用某些罗丹宁衍生物治疗高血糖和阿尔茨海默病的方法。在本方法中使用的某些罗丹宁衍生物是新颖的，因此还提供了此类化合物、其制备工艺和药物制剂。
• Compounds useful as hypoglycemic agents and for treating Alzheimer's disease
  申请人：ELI LILLY AND COMPANY

  公开号：EP0915090A1

  公开（公告）日：1999-05-12

  Provided are methods for treating hyperglycemia and Alzheimer's disease utilizing certain rhodanine derivatives. Certain of the rhodanine derivatives utilized in the instant methods are novel and, accordingly, such compounds, process for preparing same and pharmaceutical formulations thereof, are also provided.

  本发明提供了利用某些罗丹宁衍生物治疗高血糖和阿尔茨海默病的方法。在本方法中使用的某些罗丹宁衍生物是新颖的，因此还提供了此类化合物、其制备工艺和药物制剂。
• SHUKLA, J. S.;SHUKLA, ROLI, J. INDIAN CHEM. SOC., 66,(1989) N, C. 209-210
  作者：SHUKLA, J. S.、SHUKLA, ROLI

  DOI：——

  日期：——
• US5523314A
  申请人：——

  公开号：US5523314A

  公开（公告）日：1996-06-04