ethyl 2-[(E)-2-(1H-indol-3-ylmethylidene)hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate | 1489265-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 2-[(E)-2-(1H-indol-3-ylmethylidene)hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
• 英文别名: (E)-ethyl 2-(2-((1H-indol-3-yl)methylene)hydrazinyl)-4-methylthiazole-5-carboxylate；ethyl 2-[(2E)-2-(1H-indol-3-ylmethylidene)hydrazinyl]-4-methyl-1,3-thiazole-5-carboxylate
• CAS: 1489265-21-5
• 化学式: C₁₆H₁₆N₄O₂S
• 分子量: 328.395
• InChiKey: TXEVAFMZVNPKTA-GIJQJNRQSA-N

物化性质

• 沸点：
  536.9±58.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 在 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 ethyl 2-[(E)-2-(1H-indol-3-ylmethylidene)hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  Synthesis of hybrids thiazole–quinoline, thiazole–indole and their analogs: in vitro anti-proliferative effects on cancer cell lines, DNA binding properties and molecular modeling

  摘要：

  合成了喹啉-噻唑混合物，对HL-60细胞系显示出细胞毒性。电化学和光谱实验表明DNA是生物靶标。

  DOI：

  10.1039/d1nj02105b

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.
• Synthesis of hybrids thiazole–quinoline, thiazole–indole and their analogs: <i>in vitro</i> anti-proliferative effects on cancer cell lines, DNA binding properties and molecular modeling
  作者：Paulo Fernando da S. Santos-Junior、Igor José dos S. Nascimento、Edjan Carlos D. da Silva、Kadja Luana C. Monteiro、Johnnatan D. de Freitas、Samaysa de Lima Lins、Thamilla Maria S. Maciel、Bruno C. Cavalcanti、José de Brito V. Neto、Fabiane C. de Abreu、Isis M. Figueiredo、Josué Carinhanha C. Santos、Claudia do Ó Pessoa、Edeildo F. da Silva-Júnior、João X. de Araújo-Júnior、Thiago M. de Aquino

  DOI：10.1039/d1nj02105b

  日期：——

  A quinoline–thiazole hybrid was synthesized, which showed cytotoxicity against the HL-60 cell line. Electrochemical and spectroscopic experiments suggested DNA as the biological target.

  合成了喹啉-噻唑混合物，对HL-60细胞系显示出细胞毒性。电化学和光谱实验表明DNA是生物靶标。