(5Z)-5-[(3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one | 6301-12-8

• 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-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• 英文别名: 2-Mercapto-5-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-thiazol-4-one
• CAS: 6301-12-8
• 化学式: C₁₀H₆N₂O₃S₂
• 分子量: 266.3
• InChiKey: AVXJAQDWWJILLN-YVMONPNESA-N

物化性质

• 熔点：
  258 °C (decomp)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 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：
  132
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-氯-5,6-二苯基-1,2,4-三嗪 、 (5Z)-5-[(3-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one 在 potassium carbonate 作用下， 反应 4.0h， 以90%的产率得到2-(5,6-Diphenyl-[1,2,4]triazin-3-ylsulfanyl)-5-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-thiazol-4-one
  参考文献：
  名称：

  Abdel-Rahman, R. M.; Ghareib, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 496 - 500

  摘要：

  DOI：

文献信息

• Molecular modeling of drug-pathophysiological Mtb protein targets: Synthesis of some 2-thioxo-1, 3-thiazolidin-4-one derivatives as anti-tubercular agents
  作者：K.M. Noorulla、Ayyadurai Jerad Suresh、Vinod Devaraji、Bijo Mathew、Devi Umesh

  DOI：10.1016/j.molstruc.2017.07.009

  日期：2017.11

  novel 2 - thioxo - 1 , 3 - thiazolidin - 4 - one derivatives ( 5a - 5t ) were synthesized and evaluated for their antitubercular activity. The structure of the compounds was confirmed by IR, NMR and Mass Spectroscopy methods. In addition, single-crystal X-ray diffraction was performed for compound 5a . All the synthesized compounds were screened for their in - vitro antimycobacterial activity against

  摘要 合成了20种新型2-thioxo-1,3-thiazolidin-4-one衍生物(5a-5t)并评价了它们的抗结核活性。化合物的结构通过红外、核磁共振和质谱方法确认。此外，对化合物5a进行了单晶X射线衍射。所有合成的化合物均通过 Alamar Blue 测定法筛选其对 MTB（H37RV，ATCC 编号：27294）的体外抗分枝杆菌活性。化合物5r、5k、5t显示出最有效的体外活性，MIC分别为0.05、0.1、0.2μg/ml浓度，其比标准品更有效。进行分子对接和动力学模拟以找出标题化合物的合理机制。
• 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。
• Benzoxazolyl linked benzylidene based rhodanine and analogs as novel antidiabetic agents: synthesis, molecular docking, and in vitro studies
  作者：Varinder Singh、Amanjot Singh、Gagandeep Singh、Raman K. Verma、Rajiv Mall

  DOI：10.1007/s00044-021-02781-y

  日期：2021.10

  Benzoxazolyl linked meta- and para-substituted new chemical entities (5a–5h) featuring thiazolidinedione, rhodanine, hydantoin, and thiohydantoin moieties were synthesized and characterized by 1H NMR, 13C NMR, FT-IR, and HRMS spectral studies. In addition, all compounds were screened for α-glucosidase inhibitory activity and further supported by molecular docking studies carried out at the active site

  合成了具有噻唑烷二酮、罗丹宁、乙内酰脲和硫代乙内酰脲部分的苯并恶唑连接的间位和对位取代的新化学实体 ( 5a – 5h )，并通过1 H NMR、13 C NMR、FT-IR 和 HRMS 光谱研究表征。此外，与用作标准药物的阿卡波糖相比，所有化合物都筛选了 α-葡萄糖苷酶抑制活性，并得到了在 α-葡萄糖苷酶活性位点（PDB 代码：3TOP）的分子对接研究的进一步支持。在八种测试化合物中，发现5d是最有效的 α-葡萄糖苷酶抑制剂 (IC 50 = 9.48 ± 0.36 µM)，在苯环的间位取代了罗丹宁部分。
• 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。