(2-(4-methylphenyl)methylene)hydrazolyl-1,3-thiazolidin-4-one | 36951-41-4

• 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: (2-(4-methylphenyl)methylene)hydrazolyl-1,3-thiazolidin-4-one
• 英文别名: 4-methyl-benzaldehyde (4-oxo-thiazolidin-2-ylidene)-hydrazone；(2E)-2-[(4-methylphenyl)methylidenehydrazinylidene]-1,3-thiazolidin-4-one
• CAS: 36951-41-4
• 化学式: C₁₁H₁₁N₃OS
• mdl: MFCD00730755
• 分子量: 233.294
• InChiKey: DSOCMEHEONDHCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-methyl-4-(4-methylene-7-phenylhepta-1,6-dien-1-yl)benzene 在 sodium acetate 作用下， 反应 3.17h， 生成 (2-(4-methylphenyl)methylene)hydrazolyl-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Badawy, Mohammed A.; Abdel-Hady, Sayed A.; Ibrahim, Yehia A., Liebigs Annalen der Chemie, 1990, # 4, p. 393 - 395

  摘要：

  DOI：

文献信息

• An Environmentally Benign One Pot Synthesis of Pyrazole Substituted-2- hydrazolyl-4-thiazolidinones
  作者：Manisha R. Bhosle、Lalit D. Khillare、Sambhaji T. Dhumal、Ramrao A. Mane

  DOI：10.2174/1570178613666151203212817

  日期：2016.2.9

  displayed an increased spectrum of biological activities. There are several synthetic routes for the synthesis of thiazolidinone molecules but are having certain lacunas like, need of catalysts and desiccants, higher reaction temperature, longer reaction time, organic solvents and tedious work up procedure. Methods: Here an ultrasound promoted one pot multicomponent protocol is developed for 2-[(1-phenyl-3-(substituted

  背景：噻唑烷酮和吡唑是很有前途的杂环系统，极大地促进了药物化学，当吡唑核掺入其他生物动力杂环时，所得分子显示出更高的生物活性谱。噻唑烷酮分子的合成有几种合成途径，但是存在某些缺陷，例如需要催化剂和干燥剂，更高的反应温度，更长的反应时间，有机溶剂和繁琐的后处理程序。 方法：在这里开发了一种超声促进的一锅多组分方案，用于2-[（（1-苯基-3-（取代的苯基）-吡唑-4-基）]]亚甲基肼基-4-噻唑烷酮（6a-g）。在此，将新制备的底物3-（4-取代的苯基）-1-苯基-1H-吡唑-4-甲醛（5a-g）在表面活性剂的水乳液中与硫代氨基脲（2）和醋酸乙基溴（3）缩合。 ，CTAB在超声作用下。 结果：在我们的研究中，使用20摩尔％CTAB水性乳液，以良好至极佳的收率获得了标题化合物2-[（（1-苯基-3-（取代的苯基）-吡唑-4-基）]亚甲基肼基-4-噻唑烷酮在60°C的超声波照射下。 结论：我们首
• Conformational Properties and Putative Bioactive Targets for Novel Thiosemicarbazone Derivatives
  作者：Nikitas Georgiou、Antigoni Cheilari、Danai Karta、Eleni Chontzopoulou、Janez Plavec、Demeter Tzeli、Stamatia Vassiliou、Thomas Mavromoustakos

  DOI：10.3390/molecules27144548

  日期：——

  spectra an exo structure was established for both of the analogs. This experimental results were confirmed by theoretical mechanistic studies, as the lowest minima conformations derived through DFT calculations were compatible with the spatial correlations observed in the 2D-NOESY and 2D-ROESY spectra. Finally, molecular binding experiments were performed to detect the potential targets for DKI21 and DKI24

  氨基硫脲DKI21和DKI24的结构分配和构象分析通过同核和异核二维核磁共振 (NMR) 光谱（2D-COSY、2D-NOESY、2D-ROESY、2D-HSQC 和 2D-​​HMBC）进行和量子力学 (QM) 计算，使用泛函密度理论 (DFT)。此外，利用 2D-NOESY 和 2D-​​ROESY 光谱的组合为这两种类似物建立了结构。该实验结果通过理论机理研究得到证实，因为通过 DFT 计算得出的最低最小构象与在 2D-NOESY 和 2D-​​ROESY 光谱中观察到的空间相关性兼容。最后，进行分子结合实验以检测源自 SwissADMe的DKI21和DKI24的潜在靶标。计算机上的分子结合实验表明，大多数所研究的酶具有良好的结合能值。使用 preADMET 和 pKCSm 软件进行的 ADMET 计算表明，这两种分子似乎是可能的药物先导物。
• Thiocyanoacetate. III. The Synthesis of 2-Hydrazono-4-thiazolidinone Derivatives
  作者：Satoshi Kambe、Toshio Hayashi

  DOI：10.1246/bcsj.45.952

  日期：1972.3
• 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.