5-methoxy-1H-indole-3-carbothioamide | 1338059-26-9

• 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: 5-methoxy-1H-indole-3-carbothioamide
• CAS: 1338059-26-9
• 化学式: C₁₀H₁₀N₂OS
• 分子量: 206.268
• InChiKey: OYWGRGJUTWNTKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  51.04
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-methoxy-1H-indole-3-carbothioamide 在 氧气 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 36.67h， 生成 3,5-bis[1-[(4-chlorophenyl)methyl]-5-methoxyindole-3-yl]-1,2,4-thiadiazole
  参考文献：
  名称：

  好氧可见光诱导分子间 S-N 键构建：在无光敏剂条件下由硫代酰胺合成 1,2,4-噻二唑

  摘要：

  在无光敏剂的条件下，通过可见光诱导硫代酰胺的氧化环化，开发了一种伴随合成 1,2,4-噻二唑的 S-N 构建的绿色方法。

  DOI：

  10.1002/ejoc.202100440
• 作为产物：
  描述：

  5-甲氧基吲哚-3-甲醛 在 sodium hydrogen sulfide 、 甲酸 、 magnesium(II) chloride hexahydrate 、 盐酸羟胺 、 sodium formate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-methoxy-1H-indole-3-carbothioamide
  参考文献：
  名称：

  Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles

  摘要：

  A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.089

文献信息

• 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.
• Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles
  作者：Dalip Kumar、N. Maruthi Kumar、Kuei-Hua Chang、Ritika Gupta、Kavita Shah

  DOI：10.1016/j.bmcl.2011.07.089

  日期：2011.10

  A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Aerobic Visible‐Light Induced Intermolecular S−N Bond Construction: Synthesis of 1,2,4‐Thiadiazoles from Thioamides under Photosensitizer‐Free Conditions
  作者：Liang Zhuo、Shihua Xie、Hui Wang、Hongjun Zhu

  DOI：10.1002/ejoc.202100440

  日期：2021.6.21

  A green approach for S−N construction with concomitant synthesis of1,2,4-thiadiazoles was developed by visible-light induced oxidative cyclization of thioamides under photosensitizer-free conditions.

  在无光敏剂的条件下，通过可见光诱导硫代酰胺的氧化环化，开发了一种伴随合成 1,2,4-噻二唑的 S-N 构建的绿色方法。