ethyl 4-methyl-2-[(E)-2-(1-phenylethylidene)hydrazin-1-yl]-1,3-thiazole-5-carboxylate | 109406-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-methyl-2-[(E)-2-(1-phenylethylidene)hydrazin-1-yl]-1,3-thiazole-5-carboxylate
• 英文别名: 4-methyl-2-[(1-phenyl-ethylidene)-hydrazino]-thiazole-5-carboxylic acid ethyl ester；4-Methyl-2-[(1-phenyl-aethyliden)-hydrazino]-thiazol-5-carbonsaeure-aethylester；ethyl 4-methyl-2-[(2E)-2-(1-phenylethylidene)hydrazino]thiazole-5-carboxylate；ethyl 4-methyl-2-[(2E)-2-(1-phenylethylidene)hydrazinyl]-1,3-thiazole-5-carboxylate
• CAS: 109406-75-9
• 化学式: C₁₅H₁₇N₃O₂S
• 分子量: 303.385
• InChiKey: HSJDULXAYHDAAN-LICLKQGHSA-N

物化性质

• 沸点：
  432.3±37.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯乙酮 以 乙醇 为溶剂， 反应 6.0h， 生成 ethyl 4-methyl-2-[(E)-2-(1-phenylethylidene)hydrazin-1-yl]-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  取代（E）-2-（2-苄叉肼基）-4-甲基噻唑-5-羧酸酯作为15-脂氧合酶和碳酸酐酶II的双重抑制剂：合成，生化评估和对接研究。

  摘要：

  15-Lipoxygenase（15-LOX）在许多炎症性肺病（包括慢性阻塞性肺病（COPD），哮喘和慢性支气管炎）中起主要作用。15-LOX的过表达与某些特定的癌症有关，包括胰腺癌，胃癌和脑癌。类似地，在碳酸酐酶（CA）的不同同工酶之间，CA II在胰腺癌，胃癌以及脑肿瘤中表达。因此，需要新的有效的15-LOX和CA II抑制剂来进一步探索这些酶的作用并促进药物发现。为此，通过FTIR，1H和13C NMR光谱设计，合成和表征了一系列苄基二甲基-肼基取代的噻唑衍生物。然后评估衍生物抑制15-LOX和牛碳酸酐酶II（bCA II）的潜力。这些化合物大多数对15-LOX表现出极好的抑制潜能，IC50为0.12±0.002至0.69±0.5μM，对bCA II表现出中等抑制力，其中化合物5h最具活性（IC50 = 1.26±0.24μM）。最有效的化合物5a作为两种酶的双重抑制剂出现，对15-LOX的选择性是bCA

  DOI：

  10.1016/j.bbrc.2016.11.028

文献信息

• 2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies
  作者：Parameshwar Makam、Ramakrishna Kankanala、Amresh Prakash、Tharanikkarasu Kannan

  DOI：10.1016/j.ejmech.2013.08.054

  日期：2013.11

  In an attempt to discover new potent inhibitors for Mycobacterium tuberculosis (Mtb), a series of 2-(2hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were designed by considering Lipinski rule. The designed compounds were synthesized, characterized and evaluated for their inhibitory potential against Mtb, H(37)Rv, by in vitro assay. The compounds, ethyl-4methyl-2-[(E)-24]-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and ethyl-2[(E)-2-[(2-hydroxyphenyl)methylidenelhydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate, 2i showed noticeable inhibitory activity against Mtb, H37Rv with minimum inhibitory concentration (MIC) of 12.5 pM and 25 1.1M respectively. An attempt has been made to understand the mechanism of action by binding interactions of these molecules with 0-ketoacyl-ACP synthase protein through docking studies. The inhibition constants for compounds 4d and 2i were found to be 1.46 pM and 0.177 pM respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Beyer; Wolter, Chemische Berichte, 1956, vol. 89, p. 1652,1656
  作者：Beyer、Wolter

  DOI：——

  日期：——