2-(2-cyclopentylidenehydrazono)thiazolidin-4-one | 14675-89-9

• 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-cyclopentylidenehydrazono)thiazolidin-4-one
• 英文别名: (2Z)-2-(cyclopentylidenehydrazinylidene)-1,3-thiazolidin-4-one
• CAS: 14675-89-9
• 化学式: C₈H₁₁N₃OS
• mdl: MFCD00990828
• 分子量: 197.261
• InChiKey: JNYICZVILLPPLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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-cyclopentylidenehydrazono)thiazolidin-4-one 、 3-氯苄溴 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3-(3-chlorobenzyl)-2-(2-cyclopentylidenehydrazono)thiazolidin-4-one
  参考文献：
  名称：

  Identification of new anti-Candida compounds by ligand-based pharmacophore virtual screening

  摘要：

  Candida albicans represents the most prevalent microbial population in mucosal and systemic infections, usually confined to severely immunocompromised people. Considering the increase of resistant strains and the demand for new antifungal drugs endowed with innovative mechanism of action, we performed a ligand-based virtual screening in order to identify new anti-Candida compounds. Starting from a large library of natural/semisynthetic products and several published synthesized compounds, three coumarin derivatives were discovered in silico as new hit compounds and submitted to the in vitro assay in order to confirm their predicted biological activity.

  DOI：

  10.3109/14756366.2016.1156103
• 作为产物：
  描述：

  环戊酮 在 盐酸 、 三乙胺 作用下， 以 水 为溶剂， 反应 0.34h， 生成 2-(2-cyclopentylidenehydrazono)thiazolidin-4-one
  参考文献：
  名称：

  Dry Grinding Synthesis and Docking Study of Cyclopentanone-Sulfur Containing Compounds with Anti-Proliferative Activity for HepG-2 and A-549 Cancer Cell Lines

  摘要：

  背景： 干磨法是一种高效有机合成的绿色技术，具有许多优点，如温和的反应条件、环境可接受性、简单的分离和精制、以及升高的选择性和效率。 目标：本研究的目的是设计和合成环戊基亚甲基-肼)-噻唑类衍生物，使用干磨条件研究它们对两种细胞系（HepG-2和A-549）的抗肿瘤活性。 方法：在这种情况下，我们通过肼酰基和2-环戊基亚甲基肼-1-氨基甲酸酯-2-乙氧基-N-芳基-2-氧代乙酰肼基硫酸酐在几分钟内使用干磨法合成了一系列噻唑并环戊烷，产率良好。 结果：所有光谱数据都证实了所提出的结构。除了抗肿瘤活性研究外，还进行了分子对接研究，使用宏噬细胞迁移抑制因子（Pdb: 4k9g）和溶菌酶C（Pdb: 2f4a）进行了分子对接研究，它们是人类肝癌细胞（HepG-2）和肺癌细胞系（A-549）中过度表达的蛋白质。 结论：两种衍生物，9b和9d，对两种细胞系HepG-2和A-549显示出最高的抗肿瘤活性。此外，对接结果显示，与结晶配体的能量得分-4.118 Kcal/mol相比，与宏噬细胞迁移抑制因子（Pdb: 4k9g）的能量得分范围为-7.1590至-5.9364 Kcal/mol更高。此外，测试的衍生物对溶菌酶C（Pdb: 2f4a）的能量得分在-6.0802至-4.5503 Kcal/mol之间变化。

  DOI：

  10.2174/1573406418666220324155119

文献信息

• Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: Enzyme and cellular studies
  作者：Simone Carradori、Dante Rotili、Celeste De Monte、Alessia Lenoci、Melissa D'Ascenzio、Veronica Rodriguez、Patrizia Filetici、Marco Miceli、Angela Nebbioso、Lucia Altucci、Daniela Secci、Antonello Mai

  DOI：10.1016/j.ejmech.2014.04.042

  日期：2014.6

  thiazolidines and pyrimidin-4(3H)-ones, and we tested the whole library existing in our lab against human p300 and PCAF HAT enzymes. Some compounds (1x, 1c', 1d', 1i' and 2m) were more efficient than CPTH2 and CPTH6 in inhibiting the p300 HAT enzyme. When tested in human leukemia U937 and colon carcinoma HCT116 cells (100 μM, 30 h), 1x, 1i' and 2m gave higher (U937 cells) or similar (HCT116 cells) apoptosis

  最近，我们描述了一些（噻唑-2-基）azo作为抗原生动物，抗真菌和抗MAO试剂以及Gcn5 HAT抑制剂。在这些最后的化合物中，CPTH2和CPTH6在细胞中显示出HAT抑制作用和广泛的抗癌特性。为了鉴定比两个原型更有效的HAT抑制剂，我们合成了几种新的（噻唑-2-基）azo酮，包括一些相关的噻唑烷和嘧啶4（3 H）-酮，并测试了我们现有的整个文库针对人p300和PCAF HAT酶的实验室。某些化合物（1x，1c '，1d '，1i '和2m）在抑制p300 HAT酶方面比CPTH2和CPTH6更有效。在人白血病U937和结肠癌HCT116细胞（100μM，30小时）中进行测试时，1x，1i '和2m产生的凋亡（U937细胞）或类似细胞（HCT116细胞）高于CPTH6，并且在诱导细胞分化方面比CPTH6更有效（U937细胞）。
• Synthesis, biological evaluation and quantitative structure-active relationships of 1,3-thiazolidin-4-one derivatives. A promising chemical scaffold endowed with high antifungal potency and low cytotoxicity
  作者：Simone Carradori、Bruna Bizzarri、Melissa D'Ascenzio、Celeste De Monte、Rossella Grande、Daniela Rivanera、Alessanda Zicari、Emanuela Mari、Manuela Sabatino、Alexandros Patsilinakos、Rino Ragno、Daniela Secci

  DOI：10.1016/j.ejmech.2017.09.026

  日期：2017.11

  hundred compounds characterized by a 1,3-thiazolidin-4-one nucleus derivatised at the C2 with a hydrazine bridge linked to (cyclo)aliphatic or hetero(aryl) moieties, and their N-benzylated derivatives. These molecules were assayed as potential anti-Candida agents and they were shown to possess comparable, and in some cases higher biological activity than well-established topical and systemic antimycotic drugs

  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。
• 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.