2-[N'-(4-methoxybenzylidene)hydrazino]-4-methylthiazole-5-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[N'-(4-methoxybenzylidene)hydrazino]-4-methylthiazole-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-[2-[(4-methoxyphenyl)methylidene]hydrazinyl]-4-methyl-1,3-thiazole-5-carboxylate；ethyl 2-[2-[(4-methoxyphenyl)methylidene]hydrazinyl]-4-methyl-1,3-thiazole-5-carboxylate
• 化学式: C₁₅H₁₇N₃O₃S
• 分子量: 319.384
• InChiKey: GLONTBYWQCQJPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 2-[N'-(4-methoxybenzylidene)hydrazino]-4-methylthiazole-5-carboxylic acid ethyl ester 以 二氯甲烷 为溶剂， 反应 0.5h， 以72%的产率得到
  参考文献：
  名称：

  Synthesis, Anticancer Activity, and Genome Profiling of Thiazolo Arene Ruthenium Complexes

  摘要：

  Sixteen hydrazinyl-thiazolo arene ruthenium complexes of the general formula [(eta(6)-p-cymene)Ru(N,Mhydrazinyl-thiazolo)Cl]Cl were synthesized. All complexes were tested in vitro for their antiproliferative activity on three tumor cell lines (HeLa, A2780, and A2780cisR) and on a noncancerous cell line (HFL-1). A superior cytotoxic activity of the ruthenium complexes as compared to cisplatin and oxaliplatin, on both cisplatin-sensitive and cisplatin resistant ovarian cancer cells, was observed. In addition, the biological activity of two selected derivatives was evaluated using microarray gene expression assay and ingenuity pathway analysis. p53 signaling was identified as an important pathway modulated by both arene ruthenium compounds. New activated molecules such as FAS, ZMAT3, PRMT2, BBC3/PUMA, and PDCD4, whose overexpressions are correlated with overcoming resistance to cisplatin therapy, were also identified as potential targets. Moreover, the arene ruthenium complexes can be used in association with cisplatin to prevent cisplatin resistance development and synergistically to induce cell death in ovarian cancer cells.

  DOI：

  10.1021/acs.jmedchem.5b00855
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 2-[N'-(4-methoxybenzylidene)hydrazino]-4-methylthiazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  In vitro and in silico antimalarial activity of 2-(2-hydrazinyl)thiazole derivatives

  摘要：

  A series of 2-(2-hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were synthesized, characterized and evaluated their inhibitory potentials against plasmodium falciparum, NF54, by in vitro blood stage assay. The compounds, ethyl-4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and 1-(4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidenelhydrazin-1-yl]-mu 3-thiazol-5-yliethan-1-one, 5d showed significant antimalarial activity with IC50 values of 0.725 mu M and 0.648 mu M respectively. To understand the mechanism, the binding interactions between 2-(2-hydrazinyl)thiazole derivatives and trans-2-enoyl acyl carrier protein reductase of P. falciparum were studied through docking studies. The half maximal inhibitory concentration (IC50) through docking studies for the compounds, 4d and 5d were found to be 22.88 mu M and 631.84 mu M respectively. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2013.11.001

文献信息

• Facial one-pot, three-component synthesis of thiazole compounds by the reactions of aldehyde/ketone, thiosemicarbazide and chlorinated carboxylic ester derivatives
  作者：Ma Xiabing、Keyume Ablajan、Mamateli Obul、Mengnisa Seydimemet、Reyhangul Ruzi、Li Wenbo

  DOI：10.1016/j.tet.2016.03.053

  日期：2016.5

  An efficient, clean and environmentally benign reaction process was developed for the convenient and cheap synthesis of hydrazone derivatives. A series of novel thiazole compounds were synthesized via one-pot three-component reaction of aldehyde/ketone, thiosemicarbazide, and chlorinated β-keto ester catalyzed by anhydrous sodium acetate. The reactions had excellent yields in EtOH solvent. The synthetic

  为了方便和廉价地合成衍生物，开发了一种有效，清洁和环境友好的反应方法。通过醛/酮，硫代氨基脲和无水乙酸钠催化的氯化β-酮酯的一锅三组分反应合成了一系列新型噻唑化合物。该反应在EtOH溶剂中具有优异的产率。讨论了合成方法和反应机理。