(Z)-5-(2-chlorobenzylidene)-2-thioxothiazolidin-4-one | 81154-08-7

• 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: (Z)-5-(2-chlorobenzylidene)-2-thioxothiazolidin-4-one
• 英文别名: 5-(2-Chlorobenzylidene)-2-thioxo-1,3-thiazolan-4-one；(5Z)-5-[(2-chlorophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 81154-08-7
• 化学式: C₁₀H₆ClNOS₂
• mdl: MFCD04969006
• 分子量: 255.749
• InChiKey: AAIBSXUAGRXSIQ-YVMONPNESA-N

物化性质

• 熔点：
  180-181 °C(Solv: ethanol (64-17-5))
• 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：

  (Z)-5-(2-chlorobenzylidene)-2-thioxothiazolidin-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-(2-chlorobenzyliden)-4-oxo-4,5-dihydrothiazol-2-ylamino)-3-phenyl-N-tosylpropanamide
  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 、 2-氯苯甲醛 在 Fe₃O₄/SiO₂-NH₂/Cu(II) 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以94%的产率得到(Z)-5-(2-chlorobenzylidene)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  铜（II）-复合官能化磁铁矿纳米粒子：一种高效的多相纳米催化剂，用于合成 5-arylidenthiazolidine-2,4-diones 和 5-arylidene-2-thioxothiazolidin-4-one

  摘要：

  磁铁矿纳米颗粒 (MNPs) 已被证明是多相催化的有用载体。我们已经合成了用铜 (II) 络合物功能化的 Fe3O4 MNP，并测试了所得材料作为非均相纳米催化剂。对该催化剂进行了脂肪族/芳香族醛与若丹宁或噻唑烷-2,4-二酮（TZD）衍生物在乙醇中回流的羟醛缩合反应测试，得到了高产率的目标产物。环境友好的化学、反应时间短、后处理简单、产率高以及新型纳米催化剂的可重复使用性是本研究的有益特征。通过扫描电子显微镜、振动样品磁强计、热重法、X 射线衍射和能量色散 X 射线分析表征纳米催化剂。

  DOI：

  10.1007/s11243-017-0159-3

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。
• A facile synthesis of (Z)-5-(substituted)-2-(methylthio)thiazol-4(5H)-one using microwave irradiation and conventional method
  作者：Dattatraya N. Pansare、Devanand B. Shinde

  DOI：10.1016/j.tetlet.2013.12.113

  日期：2014.1

  A new effective approach to the synthesis of some new (Z)-5-(substituted)-2-thioxothiazolidin-4-one 3a–l and (Z)-5-(substituted)-2-(methylthio)thiazol-4(5H)-one 5a–l is reported under microwave irradiation as well as conventional conditions.

  一种新的有效合成一些新的（Z）-5-（取代）-2-硫代噻唑啉酮-4-one 3a - 1和（Z）-5-（取代）-2-（甲硫基）噻唑-4（据报道，在微波辐射以及常规条件下，5 H）-1 5a - l。
• Pharmaceutical Preparations Comprising Insulin, Zinc Ions and Zinc-Binding Ligand
  申请人：Kaarsholm Niels Christian

  公开号：US20090123563A1

  公开（公告）日：2009-05-14

  Novel preparations comprising branched ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The preparations have a prolonged action designed for flexible injection regimes.

  这段话的中文翻译如下：使用分支配体的新型制备物，用于R-状态胰岛素六聚体的HisB10 Zn2+位点。这些制备物具有长效作用，旨在为灵活的注射方案设计。
• Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family
  作者：Carole J.R. Bataille、Méabh B. Brennan、Simon Byrne、Stephen G. Davies、Matthew Durbin、Oleg Fedorov、Kilian V.M. Huber、Alan M. Jones、Stefan Knapp、Gu Liu、Anna Nadali、Camilo E. Quevedo、Angela J. Russell、Roderick G. Walker、Robert Westwood、Graham M. Wynne

  DOI：10.1016/j.bmc.2017.02.056

  日期：2017.5

  The PIM family of serine/threonine kinases have become an attractive target for anti-cancer drug development, particularly for certain hematological malignancies. Here, we describe the discovery of a series of inhibitors of the PIM kinase family using a high throughput screening strategy. Through a combination of molecular modeling and optimization studies, the intrinsic potencies and molecular properties of this series of compounds was significantly improved. An excellent pan-PIM isoform inhibition profile was observed across the series, while optimized examples show good selectivity over other kinases. Two PIM-expressing leukemic cancer cell lines, MV4-11 and 1(562, were employed to evaluate the in vitro anti-proliferative effects of selected inhibitors. Encouraging activities were observed for many examples, with the best example (44) giving an IC55 of 0.75 mu M against the K562 cell line. These data provide a promising starting point for further development of this series as a new cancer therapy through PIM kinase inhibition. (C) 2017 Elsevier Ltd. All rights reserved.
• OMAR M. T.; SHERIF F. A., J. PRAKT. CHEM., 1980, 322, NO 5, 835-842
  作者：OMAR M. T.、 SHERIF F. A.

  DOI：——

  日期：——