N-(2-(1H-indol-3-yl)ethyl)thiophene-2-carboxamide | 345992-25-8

• 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: N-(2-(1H-indol-3-yl)ethyl)thiophene-2-carboxamide
• 英文别名: N-[2-(1H-indol-3-yl)ethyl]thiophene-2-carboxamide
• CAS: 345992-25-8
• 化学式: C₁₅H₁₄N₂OS
• mdl: MFCD00120127
• 分子量: 270.355
• InChiKey: XPABVAIADVEYBD-UHFFFAOYSA-N

物化性质

• 沸点：
  574.6±35.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-(1H-indol-3-yl)ethyl)thiophene-2-carboxamide 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以95%的产率得到N-[2-(1H-indol-3-yl)-2-oxoethyl]thiophene-2-carboxamide
  参考文献：
  名称：

  首先报道丙基磷酸酐（T3P ®）介导的罗宾逊-加布里埃尔环。天然和非天然的5-（3-吲哚基）恶唑的合成

  摘要：

  在目前的工作中，丙基膦酸酐（T3P ®）辅助的罗宾逊-加布里埃尔环化Ñ酰基-β-oxotryptamines为2-取代-5-（3-吲哚基）恶唑已经开发的合成。在微波辐射下，反应在乙腈中顺利进行，产物的分离仅需萃取并随后结晶。无需层析。以良好至优异的产率获得了所需的产物。

  DOI：

  10.1016/j.tetlet.2019.04.024
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 色胺 在 三乙胺 作用下， 反应 1.0h， 以80%的产率得到N-(2-(1H-indol-3-yl)ethyl)thiophene-2-carboxamide
  参考文献：
  名称：

  Tryptamine derivatives disarm colistin resistance in polymyxin-resistant gram-negative bacteria

  摘要：

  The last three decades have seen a dwindling number of novel antibiotic classes approved for clinical use and a concurrent increase in levels of antibiotic resistance, necessitating alternative methods to combat the rise of multi-drug resistant bacteria. A promising strategy employs antibiotic adjuvants, non-toxic molecules that disarm antibiotic resistance. When co-dosed with antibiotics, these compounds restore antibiotic efficacy in drug-resistant strains. Herein we identify derivatives of tryptamine, a ubiquitous biochemical scaffold containing an indole ring system, capable of disarming colistin resistance in the Gram-negative bacterial pathogens Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli while having no inherent bacterial toxicity. Resistance was overcome in strains carrying endogenous chromosomally-encoded colistin resistance machinery, as well as resistance conferred by the mobile colistin resistance-1 (mcr-1) plasmid-borne gene. These compounds restore a colistin minimum inhibitory concentration (MIC) below the Clinical & Laboratory Sciences Institute (CLSI) breakpoint in all resistant strains.

  DOI：

  10.1016/j.bmc.2019.03.019

文献信息

• An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y
  作者：Suresh Babu Meruva、Akula Raghunadh、Raghavendra Rao Kamaraju、U K Syam Kumar、P K Dubey

  DOI：10.3762/bjoc.10.45

  日期：——

  A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation–Bischler–Napieralski reaction conditions using tryptamine and 2,2-dibromo-1-phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids.

  一种新的合成方法已经开发出来，用于合成二氢-β-咔啉衍生物，采用氧化酰胺化-Bischler-Napieralski反应条件，使用色胺和2,2-二溴-1-苯乙酮作为关键起始材料。使用这种方法，合成了多种二氢-β-咔啉衍生物，收率在中等到良好之间。尝试将这些二氢-β-咔啉转化为天然存在的尤地斯托明生物碱。
• Tryptamine derivatives disarm colistin resistance in polymyxin-resistant gram-negative bacteria
  作者：William T. Barker、Courtney E. Chandler、Roberta J. Melander、Robert K. Ernst、Christian Melander

  DOI：10.1016/j.bmc.2019.03.019

  日期：2019.5

  The last three decades have seen a dwindling number of novel antibiotic classes approved for clinical use and a concurrent increase in levels of antibiotic resistance, necessitating alternative methods to combat the rise of multi-drug resistant bacteria. A promising strategy employs antibiotic adjuvants, non-toxic molecules that disarm antibiotic resistance. When co-dosed with antibiotics, these compounds restore antibiotic efficacy in drug-resistant strains. Herein we identify derivatives of tryptamine, a ubiquitous biochemical scaffold containing an indole ring system, capable of disarming colistin resistance in the Gram-negative bacterial pathogens Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli while having no inherent bacterial toxicity. Resistance was overcome in strains carrying endogenous chromosomally-encoded colistin resistance machinery, as well as resistance conferred by the mobile colistin resistance-1 (mcr-1) plasmid-borne gene. These compounds restore a colistin minimum inhibitory concentration (MIC) below the Clinical & Laboratory Sciences Institute (CLSI) breakpoint in all resistant strains.
• First reported propylphosphonic anhydride (T3P®) mediated Robinson–Gabriel cyclization. Synthesis of natural and unnatural 5-(3-indolyl)oxazoles
  作者：Tímea Szabó、András Dancsó、Péter Ábrányi-Balogh、Balázs Volk、Mátyás Milen

  DOI：10.1016/j.tetlet.2019.04.024

  日期：2019.5

  In the present work, a propylphosphonic anhydride (T3P®) assisted Robinson–Gabriel cyclization of N-acyl-β-oxotryptamines for the synthesis of 2-substituted-5-(3-indolyl)oxazoles has been developed. The reactions proceeded smoothly in acetonitrile under microwave irradiation, and the product isolation required only an extraction and subsequent crystallization; no chromatography was necessary. The desired

  在目前的工作中，丙基膦酸酐（T3P ®）辅助的罗宾逊-加布里埃尔环化Ñ酰基-β-oxotryptamines为2-取代-5-（3-吲哚基）恶唑已经开发的合成。在微波辐射下，反应在乙腈中顺利进行，产物的分离仅需萃取并随后结晶。无需层析。以良好至优异的产率获得了所需的产物。