6-methoxyindole-3-carbothioamide | 265111-06-6

• 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: 6-methoxyindole-3-carbothioamide
• 英文别名: 6-methoxyindole-3-thiocarboxamide；6-methoxy-1H-indole-3-carbothioamide
• CAS: 265111-06-6
• 化学式: C₁₀H₁₀N₂OS
• 分子量: 206.268
• InChiKey: GKXQPJPFARHRIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxyindole-3-carbothioamide 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到3,5-bis(6-methoxy-1H-indol-3-yl)-1,2,4-thiadiazole
  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
• 作为产物：
  描述：

  6-甲氧基吲哚 在 吡啶 、 盐酸 、 盐酸羟胺 、 sodium acetate 、 乙酸酐 、 硫代乙酰胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 6-methoxyindole-3-carbothioamide
  参考文献：
  名称：

  植物病原性真菌Camalexins，其生物等排体和类似物在植物病原性真菌Alternaria braciicicola中的代谢

  摘要：

  据报道，铜绿链霉菌对植物抗毒素camalexin（1），1-甲基camalexin（10）和6-甲氧基camalexin（11）的代谢及其抗真菌活性。这项工作建立了camalexins缓慢地生物转化（约六天）为相应的吲哚-3-硫代羧酰胺，然后将其进一步转化为吲哚-3-羧酸。这些代谢物对油菜曲霉的抑制作用远小于亲本卡莱姆毒素，表明这些酶介导的转化是解毒作用。此外，分析了卡莱姆毒素的合成异构体和生物异构体的代谢（1）表明噻唑环中的甘氨毒素的异构体没有被代谢。基于这些结果，提出了导致吲哚-3-硫代羧酰胺形成的潜在中间体。

  DOI：

  10.1016/j.bmc.2013.05.026

文献信息

• Syntheses and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone and bis(indolyl)pyrazine: analogues of cytotoxic marine bis(indole) alkaloid
  作者：Biao Jiang、Xiao-Hui Gu

  DOI：10.1016/s0968-0896(99)00290-4

  日期：2000.2

  2,4-Bis(3'-indolyl)thiazoles, 3,5-bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis(3'-indolyl)pyrazine were synthesized and evaluated for cytotoxic activity against diverse human cancer cell lines by the National Cancer Institute. These compounds demonstrated significant inhibitory effects in the growth of a range of cancer cell lines. 2,4-Bis(3'-indolyl)thiazole displayed selective cytotoxicity against certain leukemia cell lines with GI(50) values in the low micromolar range while the substituted derivatives showed a broad spectrum of cytotoxic activity. 3,5-Bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis[3'-(N-methyl-indolyl)]pyrazine possessed strong inhibitory activity against a wide range of human tumor cell lines. The mechanism of action remained unknown. The results suggested that 2,4-bis(3'-indolyl)thiazoles, 3,5-bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis[3'-(N-methyl-indolyl)] pyrazine offer potential as lead compounds for the discovery of anticancer agents. (C) 2000 Elsevier Science 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.
• Metabolism of the phytoalexins camalexins, their bioisosteres and analogues in the plant pathogenic fungus Alternaria brassicicola
  作者：M. Soledade C. Pedras、Abbas Abdoli

  DOI：10.1016/j.bmc.2013.05.026

  日期：2013.8

  The metabolism of the phytoalexins camalexin (1), 1-methylcamalexin (10) and 6-methoxycamalexin (11) by Alternaria brassicicola and their antifungal activity is reported. This work establishes that camalexins are slowly biotransformed (ca. six days) to the corresponding indole-3-thiocarboxamides, which are further transformed to the indole-3-carboxylic acids. These metabolites are substantially less

  据报道，铜绿链霉菌对植物抗毒素camalexin（1），1-甲基camalexin（10）和6-甲氧基camalexin（11）的代谢及其抗真菌活性。这项工作建立了camalexins缓慢地生物转化（约六天）为相应的吲哚-3-硫代羧酰胺，然后将其进一步转化为吲哚-3-羧酸。这些代谢物对油菜曲霉的抑制作用远小于亲本卡莱姆毒素，表明这些酶介导的转化是解毒作用。此外，分析了卡莱姆毒素的合成异构体和生物异构体的代谢（1）表明噻唑环中的甘氨毒素的异构体没有被代谢。基于这些结果，提出了导致吲哚-3-硫代羧酰胺形成的潜在中间体。