2-(2-cyclohexylidenehydrazono)thiazolidin-4-one | 71299-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-(2-cyclohexylidenehydrazono)thiazolidin-4-one
• 英文别名: 2-Cyclohexylidenehydrazono-4-oxo-thiazolidine；thiazolidine-2,4-dione 2-cyclohexylidenehydrazone；Thiazolidin-2,4-dion-2-cyclohexylidenhydrazon；(2E)-2-(cyclohexylidenehydrazono)thiazolidin-4-one；(2E)-2-(cyclohexylidenehydrazinylidene)-1,3-thiazolidin-4-one
• CAS: 71299-80-4
• 化学式: C₉H₁₃N₃OS
• mdl: MFCD00824887
• 分子量: 211.288
• InChiKey: VUXBJWFSWFTRJX-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C
• 沸点：
  347.2±25.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  79.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-cyclohexylidenehydrazono)thiazolidin-4-one 、 4-丁氧基苯甲醛 在 哌啶 作用下， 以 四氢呋喃 为溶剂， 生成 4-butoxy-benzaldehyde (4-oxo-thiazolidin-2-ylidene)-hydrazone
  参考文献：
  名称：

  Murza,M.M. et al., Journal of Organic Chemistry USSR (English Translation), 1979, vol. 15, p. 959 - 961

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-(2-cyclohexylidenehydrazono)thiazolidin-4-one
  参考文献：
  名称：

  1,3-噻唑烷丁-4-酮衍生物的合成，生物学评估和定量构效关系。具有高抗真菌效力和低细胞毒性的有前途的化学支架

  摘要：

  参考有关噻唑烷酮支架各种生物学特性的最新研究报告，我们合成了一百多种化合物，这些化合物的特征是1,2噻唑烷酮-4-酮核在C2处衍生化，并带有与（环）脂族连接的肼桥。或杂（芳基）部分，以及它们的N-苄基衍生物。这些分子被作为潜在的抗念珠菌药物进行了分析，显示它们具有与成熟的局部和全身性抗真菌药物（即克霉唑，氟康唑，酮康唑，咪康唑，噻康唑，两性霉素B）相当的生物活性，在某些情况下具有更高的生物学活性。具有最低MIC的化合物进行了进一步测试，以评估其细胞毒性作用（CC 50）在Hep2细胞上，证明了其相对安全性。最后，使用QSAR和3-D QSAR模型预测1,3-噻唑烷丁-4-酮支架的假定化学修饰，以设计针对念珠菌的新的和潜在的更具活性的化合物。

  DOI：

  10.1016/j.ejmech.2017.09.026

文献信息

• Synthesis of novel N‐substitutedphenyl‐6‐oxo‐3‐phenylpyridazine derivatives as cyclooxygenase‐2 inhibitors
  作者：Abida Khan、Anupama Diwan、Hamdy K Thabet、Mohd Imran

  DOI：10.1002/ddr.21655

  日期：2020.8

  N‐substitutedphenyl‐6‐oxo‐3‐phenylpyridazines as COX‐2 inhibitors have been developed (Supplementary material Appendix 1). The novel aldehyde 3 was prepared by reacting 6‐phenylpyridazin‐3(2H)‐one with 4‐fluorobenzaldehyde. The aldehyde 3 was reacted with different hydrazines and thiazolidin‐4‐ones to obtain the novel N‐substitutedphenyl‐6‐oxo‐3‐phenylpyridazine derivatives. These were assessed for their anti‐inflammatory

  一些新型的非致溃疡性 N-取代苯基-6-氧代-3-苯基哒嗪作为 COX-2 抑制剂被开发出来（补充材料附录 1）。通过 6-苯基哒嗪-3( 2H )-one 与 4-氟苯甲醛反应制备了新型醛3。醛3与不同的肼和噻唑啉-4-酮反应得到新型N-取代苯基-6-氧代-3-苯基哒嗪衍生物。评估了它们的抗炎潜力和胃溃疡形成作用。还进行了分子对接研究。光谱数据与化合物的分配结构一致。化合物4a (IC 50 = 17.45 nm；p < .05)，4b (IC 50 = 17.40 nm; p < .05)、5a (IC 50 = 16.76 nm; p < .05) 和10 (IC 50 = 17.15 nm; p < .05) 比塞来昔布（IC 50 = 17.79 nm；p < .05）。这些发现与4a、4b、5a和10的分子对接研究一致。在体内的抗炎轮廓图4a，图4b，图5a，和10也优于塞来昔
• Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 kinase inhibitors
  作者：Peng-Cheng Lv、Chang-Fang Zhou、Jin Chen、Peng-Gang Liu、Kai-Rui Wang、Wen-Jun Mao、Huan-Qiu Li、Ying Yang、Jing Xiong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2009.10.051

  日期：2010.1

  Two series of thiazolidinone derivatives designing for potential EGFR and HER-2 kinase inhibitors have been discovered. Some of them exhibited significant EGFR and HER-2 inhibitory activity. Compound 2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one (12) displayed the most potent inhibitory activity (IC50 = 0.09 mu M for EGFR and IC50 = 0.42 mu M for HER-2), comparable to the positive control erlotinib. Docking simulation was performed to position compound 12 into the EGFR active site to determine the probable binding model. Antiproliferative assay results indicating that some of the thiazolidinone derivatives own high antiproliferative activity against MCF-7. Compound 12 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent. (C) 2009 Elsevier Ltd. All rights reserved.
• Anti-Candida activity and cytotoxicity of a large library of new N-substituted-1,3-thiazolidin-4-one derivatives
  作者：Celeste De Monte、Simone Carradori、Bruna Bizzarri、Adriana Bolasco、Federica Caprara、Adriano Mollica、Daniela Rivanera、Emanuela Mari、Alessandra Zicari、Atilla Akdemir、Daniela Secci

  DOI：10.1016/j.ejmech.2015.10.048

  日期：2016.1

  On the basis of the recent findings about the biological properties of thiazolidinones and taking into account the encouraging results about the antifungal activity of some (thiazol-2-yl)hydrazines, new N-substituted heterocyclic derivatives were designed combining the thiazolidinone nucleus with the hydrazonic portion. In details, 1,3-thiazolidin-4-ones bearing (cyclo)aliphatic or (hetero)aromatic moieties linked to the N1-hydrazine at C2 were synthesized and classified into three series according to the aromatic or bicyclic rings connected to the lactam nitrogen of the thiazolidinone. These molecules were assayed for their anti-Candida effects in reference to the biological activity of the conventional topic (clotrimazole, miconazole, tioconazole) and systemic drugs (fluconazole, ketoconazole, amphotericin B). Finally, we investigated the selectivity against fungal cells by testing the compounds endowed with the best MICs on Hep2 cells in order to assess their cell toxicity (CC50) and we noticed that two derivatives were less cytotoxic than the reference drug clotrimazole. Moreover, a preliminary molecular modelling approach has been performed against lanosterol 14-alpha demethylase (CYP51A1) to rationalize the activity of the tested compounds and to specify the target protein or enzyme. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii
  作者：Melissa D'Ascenzio、Bruna Bizzarri、Celeste De Monte、Simone Carradori、Adriana Bolasco、Daniela Secci、Daniela Rivanera、Nathan Faulhaber、Claudia Bordón、Lorraine Jones-Brando

  DOI：10.1016/j.ejmech.2014.08.046

  日期：2014.10

  We designed and synthesized a large number of novel thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii activity. This scaffold was functionalized at the N1-hydrazine portion with aliphatic, cycloaliphatic and (hetero)aromatic moieties. Then, a benzyl pendant was introduced at the lactamic NH of the core nucleus to evaluate the influence of this chemical modification on biological activity. The compounds were subjected to several in vitro assays to assess their anti-parasitic efficacy, cytotoxicity on fibroblasts, inhibition of tachyzoite invasion/attachment and replication after treatment. Results showed that fourteen of these thiazole-based compounds compare favorably to control compound trimethoprim in terms of parasite growth inhibition. (c) 2014 Elsevier Masson SAS. All rights reserved.
• MURZA M. M.; KUVATOV Z. X.; MINLIBAEVA A. N., ZH. ORGAN. XIMII, 1979, 15, HO 5, 1074-1076,
  作者：MURZA M. M.、 KUVATOV Z. X.、 MINLIBAEVA A. N.

  DOI：——

  日期：——