7,8-dimethoxy-1-oxo-1H-isothiochromene-3-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异硫色烯
• 英文名称: 7,8-dimethoxy-1-oxo-1H-isothiochromene-3-carboxylic acid methyl ester
• 英文别名: 7,8-dimethoxy-1-oxo-1H-isothiochromene-3-carboxylic acid methyl ester；7,8-Dimethoxy-1-oxo-1H-isothiochromen-3-carbonsaeure-methylester；Methyl 7,8-dimethoxy-thioisocumarin-3-carboxylat；methyl 7,8-dimethoxy-1-oxo-1H-isothiochromene-3-carboxylate；methyl 7,8-dimethoxy-1-oxoisothiochromene-3-carboxylate
• 化学式: C₁₃H₁₂O₅S
• 分子量: 280.301
• InChiKey: ROGSFUVOCHXWGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-羧基-3,4-二甲氧基苯甲醛 在 氯化亚砜 、 sodium acetate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 7,8-dimethoxy-1-oxo-1H-isothiochromene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Isothiocoumarin-3-carboxylic acid derivatives: Synthesis, anticancer and antitrypanosomal activity evaluation

  摘要：

  A series of new isothiocoumarin-3-carboxylic acids derivatives had been obtained based on the 5-arylidenerhodanines hydrolysis. Anticancer activity screening allowed identification of 7,8-dimethoxyl-oxo-1H-isothiochromene-3-carboxylic acid (4-phenylthiazol-2-yl)-amide (30) with the highest level of antimitotic activity (GI(50) NCI-H322MINSC Lung Cancer = 1.28 mu M). Evaluation of the antitrypanosomal activity against Trypanosoma brucei brucei showed that investigated compounds did not exhibit significant antiparasitic effects. Additionally, the most pharmacologically attractive compounds were nontoxic and well tolerated by the experimental animals. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.028

文献信息

• 271. 1 : 2-Dihydro-2-thianaphthalene derivatives. Part I. Preparation and reactions of 1 : 2-dihydro-1-keto-2-thianaphthalenes
  作者：D. J. Dijksman、G. T. Newbold

  DOI：10.1039/jr9510001213

  日期：——
• Isothiocoumarin-3-carboxylic acid derivatives: Synthesis, anticancer and antitrypanosomal activity evaluation
  作者：Danylo Kaminskyy、Anna Kryshchyshyn、Ihor Nektegayev、Olexandr Vasylenko、Philippe Grellier、Roman Lesyk

  DOI：10.1016/j.ejmech.2014.01.028

  日期：2014.3

  A series of new isothiocoumarin-3-carboxylic acids derivatives had been obtained based on the 5-arylidenerhodanines hydrolysis. Anticancer activity screening allowed identification of 7,8-dimethoxyl-oxo-1H-isothiochromene-3-carboxylic acid (4-phenylthiazol-2-yl)-amide (30) with the highest level of antimitotic activity (GI(50) NCI-H322MINSC Lung Cancer = 1.28 mu M). Evaluation of the antitrypanosomal activity against Trypanosoma brucei brucei showed that investigated compounds did not exhibit significant antiparasitic effects. Additionally, the most pharmacologically attractive compounds were nontoxic and well tolerated by the experimental animals. (C) 2014 Elsevier Masson SAS. All rights reserved.