2-(1H-indol-3-yl)thiazole-4-carboxylic acid

• 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: 2-(1H-indol-3-yl)thiazole-4-carboxylic acid
• 英文别名: 2-(1H-indol-3-yl)-1,3-thiazole-4-carboxylic acid
• 化学式: C₁₂H₈N₂O₂S
• 分子量: 244.274
• InChiKey: FTPLYXUNUZSEFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1H-indol-3-yl)thiazole-4-carboxylic acid 、 3,4-二甲氧基苯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 以79%的产率得到N-(3,4-dimethoxyphenyl)-2-(1H-indol-3-yl)thiazole-4-carboxamide
  参考文献：
  名称：

  2-(3′-Indolyl)-N-arylthiazole-4-carboxamides: Synthesis and evaluation of antibacterial and anticancer activities

  摘要：

  A new series of 2-(3'-indolyl)-N-arylthiazole-4-carboxamides 17a-p has been designed and synthesized. Initial reaction of readily available thioamides 15 with bromopyruvic acid under refluxing conditions produced different thiazole carboxylic acids 16 which upon coupling with arylamines by using EDCI.HCl and HOBt afforded diverse arylthiazole-4-carboxamides 17a-p in 78-87% yields. Antibacterial activity evaluation against Gram-positive and Gram-negative bacterial strains led to compounds 17i-k and 17o as potent and selectively (Gram-negative) antibacterial agents. The cytotoxicity of thiazole carboxamides 17a-p was also evaluated on a panel of human cancer cell lines. Among the tested derivatives, compounds 17i (IC50 = 8.64 mu M; HEK293T) and 17l (IC50 = 3.41 mu M; HeLa) were identified as the most potent analogues of the series. Preliminary mechanism of action studies of thiazole carboxamide 17i suggested that its cytotoxicity against HeLa cells involves the induction of cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.105
• 作为产物：
  描述：

  1H-吲哚-3-羰基羧酸酰铵 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 15.0h， 生成 2-(1H-indol-3-yl)thiazole-4-carboxylic acid
  参考文献：
  名称：

  甲氧基Camalexins和相关化合物：合成，抗真菌活性和抑制油菜素氧化酶

  摘要：

  植物抗毒素xin camalexin是一种竞争性的油菜花青素氧化酶抑制剂，它是一种对植物油菜青素黄铜素进行解毒的酶，由具有重要经济意义的植物病原体产生。因此，camalexin支架指导了花青素解毒抑制剂的设计。为了进一步了解camalexin相关化合物的结构-活性关系，进行了单甲氧基和二甲氧基camalexins的合成。使用Ayer's方法由相应的甲氧基吲哚制备四种单甲氧基Camalexins以及4,6-二甲氧基和5,7-二甲氧基Camalexin。使用Hantzsch反应由相应的二甲氧基吲哚-3-硫代羧酰胺制备二甲氧基衍生物。但是，该方法不适用于4,6-二甲氧基和5的合成 由于相应的吲哚-3-硫代羧酰胺的反应性较低，因此存在7-二甲氧基Camalexins。研究了所有甲氧基camalexins和十种camalexin相关化合物的抗真菌活性和brastinin氧化酶抑制活性。在所评估的20

  DOI：

  10.1016/j.bmc.2018.07.030

文献信息

• Methoxycamalexins and related compounds: Syntheses, antifungal activity and inhibition of brassinin oxidase
  作者：M. Soledade C. Pedras、Abbas Abdoli

  DOI：10.1016/j.bmc.2018.07.030

  日期：2018.8

  reaction; however, this method did not work for the syntheses of 4,6-dimethoxy and 5,7-dimethoxycamalexins due to the lower reactivities of the corresponding indole-3-thiocarboxamides. The antifungal activity and brassinin oxidase inhibitory activity of all methoxycamalexins and ten camalexin related compounds were investigated. Among the 20 compounds evaluated, monomethoxycamalexins were stronger antifungals

  植物抗毒素xin camalexin是一种竞争性的油菜花青素氧化酶抑制剂，它是一种对植物油菜青素黄铜素进行解毒的酶，由具有重要经济意义的植物病原体产生。因此，camalexin支架指导了花青素解毒抑制剂的设计。为了进一步了解camalexin相关化合物的结构-活性关系，进行了单甲氧基和二甲氧基camalexins的合成。使用Ayer's方法由相应的甲氧基吲哚制备四种单甲氧基Camalexins以及4,6-二甲氧基和5,7-二甲氧基Camalexin。使用Hantzsch反应由相应的二甲氧基吲哚-3-硫代羧酰胺制备二甲氧基衍生物。但是，该方法不适用于4,6-二甲氧基和5的合成 由于相应的吲哚-3-硫代羧酰胺的反应性较低，因此存在7-二甲氧基Camalexins。研究了所有甲氧基camalexins和十种camalexin相关化合物的抗真菌活性和brastinin氧化酶抑制活性。在所评估的20
• 2-(3′-Indolyl)-N-arylthiazole-4-carboxamides: Synthesis and evaluation of antibacterial and anticancer activities
  作者：Mukund P. Tantak、Jing Wang、Rajnish Prakash Singh、Anil Kumar、Kavita Shah、Dalip Kumar

  DOI：10.1016/j.bmcl.2015.07.105

  日期：2015.10

  A new series of 2-(3'-indolyl)-N-arylthiazole-4-carboxamides 17a-p has been designed and synthesized. Initial reaction of readily available thioamides 15 with bromopyruvic acid under refluxing conditions produced different thiazole carboxylic acids 16 which upon coupling with arylamines by using EDCI.HCl and HOBt afforded diverse arylthiazole-4-carboxamides 17a-p in 78-87% yields. Antibacterial activity evaluation against Gram-positive and Gram-negative bacterial strains led to compounds 17i-k and 17o as potent and selectively (Gram-negative) antibacterial agents. The cytotoxicity of thiazole carboxamides 17a-p was also evaluated on a panel of human cancer cell lines. Among the tested derivatives, compounds 17i (IC50 = 8.64 mu M; HEK293T) and 17l (IC50 = 3.41 mu M; HeLa) were identified as the most potent analogues of the series. Preliminary mechanism of action studies of thiazole carboxamide 17i suggested that its cytotoxicity against HeLa cells involves the induction of cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.