5-bromoindole-3-carbothioamide | 265111-05-5

• 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-bromoindole-3-carbothioamide
• 英文别名: 1H-5-bromoindole-3-carbothioamide；5-bromo-1H-indole-3-thiocarboxamide；5-bromo-1H-indole-3-carbothioamide
• CAS: 265111-05-5
• 化学式: C₉H₇BrN₂S
• 分子量: 255.138
• InChiKey: SMQZOWAHENSVDM-UHFFFAOYSA-N

物化性质

• 沸点：
  450.7±48.0 °C(Predicted)
• 密度：
  1.764±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromoindole-3-carbothioamide 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 、 1,4-二氧六环 为溶剂， 反应 12.5h， 生成 2-(5-bromo-1H-indol-3-yl)-N-(3,4,5-trimethoxyphenyl)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：

  5-溴吲哚 在 sodium hydrogen sulfide 、 magnesium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 5-bromoindole-3-carbothioamide
  参考文献：
  名称：

  含噻唑和恶唑部分的诺托普汀类似物的优化，构效关系和作用方式

  摘要：

  植物病害严重危害植物健康，很难控制。设计，合成和评估了一系列降钙素原类似物的抗病毒活性和杀真菌活性。这些化合物大多数显示出比病毒唑更高的抗病毒活性。具有优异抗病毒活性的化合物1d，1e和12a出现为新型抗病毒先导化合物，其中1e被选择用于进一步的抗病毒机制研究。机制研究结果表明，这些化合物可能通过聚集病毒颗粒来阻止其在植物中的移动，从而发挥抗病毒作用。进一步的杀真菌活性测试表明，降钙素原类似物具有广谱杀真菌活性。与商业杀菌剂多菌灵和百菌清相比，化合物2p和2f表现出更高的抗黑斑病菌的抗真菌活性。当前的研究为降钙素原类似物在植物保护中的应用奠定了基础。

  DOI：

  10.1021/acs.jafc.9b04093

文献信息

• Discovery of Phytoalexin Camalexin and Its Derivatives as Novel Antiviral and Antiphytopathogenic-Fungus Agents
  作者：Ancai Liao、Lin Li、Tienan Wang、Aidang Lu、Ziwen Wang、Qingmin Wang

  DOI：10.1021/acs.jafc.1c07805

  日期：2022.3.2

  varieties of botanical pesticides based on allelochemicals is one of the important ways to create efficient and green pesticides. Here, a series of camalexin derivatives based on a phytoalexin camalexin scaffold were designed, synthesized, and assessed for their antiviral and fungicidal activities systematically. Most of these camalexin derivatives exhibited better antiviral activities against tobacco mosaic

  为了应对植物病毒和病原真菌的入侵，高等植物会产生防御性化感物质。基于化感化学物质寻找植物源农药候选品种是打造高效绿色农药的重要途径之一。在这里，设计、合成了一系列基于植物抗毒素camalexin 支架的camalexin 衍生物，并系统地评估了它们的抗病毒和杀真菌活性。这些camalexin衍生物中的大多数对烟草花叶病毒（TMV）表现出比对照抗病毒剂利巴韦林更好的抗病毒活性。在相同的试验条件下，化合物3d、5a、5d和10f - 10h的抗TMV活性发现与宁南霉素相当或优于宁南霉素，这是一种具有优异保护作用的农用胞嘧啶核苷抗生素。抗病毒机制研究表明，化合物5a可引起20S CP盘融合解体，从而影响病毒颗粒的组装。分子对接结果表明化合物3d、5a、10f与TMV CP之间存在明显的氢键。化合物5a和10f与 TMV CP的结合常数也使用荧光滴定法计算。这些 camalexin 衍生物还具有广
• 植保素camalexin衍生物及其制备方法和用途
  申请人：河北工业大学

  公开号：CN114380815A

  公开（公告）日：2022-04-22

  本发明为植保素camalexin衍生物及其制备方法和用途。所述植保素camalexin衍生物的结构通式如I所示，该衍生物在生物碱camalexin的基础上引入了新的取代基团，将天然产物camalexin的核心骨架吲哚结构单元中5位引入溴原子且在噻唑结构单元中4位引入酰肼腙官能团，生成系列camalexin衍生物。本发明的生物碱植保素camalexin衍生物具有很好的抗植物病毒活性和广谱的杀植物病原菌活性。
• 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.
• 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.