1-(1H-indol-3-yl)-2-(pyrrolidin-1-yl)ethane-1,2-dione | 16292-55-0

• 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: 1-(1H-indol-3-yl)-2-(pyrrolidin-1-yl)ethane-1,2-dione
• 英文别名: 1-(1H-indol-3-yl)-2-pyrrolidin-1-ylethane-1,2-dione
• CAS: 16292-55-0
• 化学式: C₁₄H₁₄N₂O₂
• mdl: MFCD00442727
• 分子量: 242.277
• InChiKey: YGWYYPSWJRQAGM-UHFFFAOYSA-N

物化性质

• 溶解度：
  >36.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1H-indol-3-yl)-2-(pyrrolidin-1-yl)ethane-1,2-dione 在 lithium aluminium tetrahydride 作用下， 生成 3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole
  参考文献：
  名称：

  Barlow; Khan, British Journal of Pharmacology and Chemotherapy, 1959, vol. 14, p. 99,101

  摘要：

  DOI：
• 作为产物：
  描述：

  吲哚-3-乙醛酰氯 在 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 1-(1H-indol-3-yl)-2-(pyrrolidin-1-yl)ethane-1,2-dione
  参考文献：
  名称：

  Sulfur rich 2-mercaptobenzothiazole and 1,2,3-triazole conjugates as novel antitubercular agents

  摘要：

  A series of benzfused heterocyclic derivatives such as amide conjugates of 2-(benzo[d]thiazol-2-ylthio) acetic acid with aromatic/aliphatic/cyclic secondary amines (5a-5o & 8a-8m); 1,2,3-triazole conjugates of 2-mercaptobenzothiazoles and amide conjugates of indole-3-glyoxalic acid with cyclic secondary amines (14a-14g) have been synthesized and were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth microdilution assay method. Compounds 8b, 8f, 8g and 8l inhibited the growth of the H37Rv strain at concentrations of 8 mu g/mL. These compounds (8b, 8f, 8g and 8l) have been further identified as bactericidal and are completely killing the microbes at 32-64 mu g/mL concentrations. Molecular docking studies of the active compounds reveal that these compounds are targeting DprE1 and may act as DprE1 inhibitors. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.017

文献信息

• Synthesis and evaluation of N1-alkylindole-3-ylalkylammonium compounds as nicotinic acetylcholine receptor ligands
  作者：Edwin G. Pérez、Bruce K. Cassels、Christoph Eibl、Daniela Gündisch

  DOI：10.1016/j.bmc.2012.04.050

  日期：2012.6

  In this study thirty-three novel indole derivatives were designed and synthesized based on the structure of deformylflustrabromine B (1), a metabolite isolated from the marine bryozoan Flustra foliacea L. The syntheses were carried out using standard methodologies and in good yields. The molecules were tested for their affinities for the alpha 4 beta 2*, alpha 3 beta 4*, alpha 7* and (alpha 1)(2)beta 1 gamma delta nicotinic acetylcholine receptor (nAChR) sub-types. Binding assays showed that, among these ligands, compound 7c exhibited the highest affinity with K-i = 136.1, 93.9 and 862.4 nM for the alpha 4 beta 2*, alpha 3 beta 4*, and alpha 7* nAChRs subtypes, respectively. These results indicated that the indole core might be a useful scaffold for the development of new potent and selective nAChR ligands. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of indole-based new scaffolds for antimicrobial activities—Identification of promising candidates
  作者：Palwinder Singh、Puja Verma、Bhawna Yadav、Sneha S. Komath

  DOI：10.1016/j.bmcl.2011.04.001

  日期：2011.6

  Search for new antimicrobial agents led to the synthesis of series of N-1, C-3 and C-5 substituted bis-indoles. Their evaluation for antifungal and antibacterial activities resulted in the optimization of pyrrolidine/morpholine/N-benzyl moiety at the C-3 end and propane/butane/xylidine groups as linkers between two indoles for significant inhibition of microbial growth. Preliminary investigations have identified three highly potent antimicrobial agents. Dockings of these molecules in the active sites of lanosterol demethylase, dihydrofolate reductase and topoisomerase II indicate their strong interactions with these enzymes. (C) 2011 Elsevier Ltd. All rights reserved.
• N-1, C-3 substituted indoles as 5-LOX inhibitors—In vitro enzyme immunoaasay, mass spectral and molecular docking investigations
  作者：Palwinder Singh、Pooja

  DOI：10.1016/j.bmcl.2012.12.068

  日期：2013.3

  Based upon the structures of some known 5-LOX inhibitors, a set of five compounds carrying appropriate substituents at N-1 and C-3 of indole were synthesized and investigated for 5-LOX inhibitory activities. Fifty percent inhibitory concn (IC50) of these compounds ranges from 0.6 to 5 mu M and found to be comparable to that of clinically used 5-LOX inhibitor, zileuton. The compounds under present investigations exhibited appreciable interactions with 5-LOX as apparent from their association constants calculated from the mass spectral data. Compound 5a with a tosyl group at N-1 and pyrolidinyl-1,2-dione substituent at C-3 of indole, exhibiting IC50 0.6 mu M and stoichiometry of 1:7 in the enzyme-compound complex was identified as highly potent 5-LOX inhibitor and seems to be suitable for further investigations. (C) 2012 Elsevier Ltd. All rights reserved.
• Barlow; Khan, British Journal of Pharmacology and Chemotherapy, 1959, vol. 14, p. 99,101
  作者：Barlow、Khan

  DOI：——

  日期：——
• Sulfur rich 2-mercaptobenzothiazole and 1,2,3-triazole conjugates as novel antitubercular agents
  作者：Fauzia Mir、Syed Shafi、M.S. Zaman、Nitin Pal Kalia、Vikrant S. Rajput、Chaitanya Mulakayala、Naveen Mulakayala、Inshad A. Khan、M.S. Alam

  DOI：10.1016/j.ejmech.2014.02.017

  日期：2014.4

  A series of benzfused heterocyclic derivatives such as amide conjugates of 2-(benzo[d]thiazol-2-ylthio) acetic acid with aromatic/aliphatic/cyclic secondary amines (5a-5o & 8a-8m); 1,2,3-triazole conjugates of 2-mercaptobenzothiazoles and amide conjugates of indole-3-glyoxalic acid with cyclic secondary amines (14a-14g) have been synthesized and were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth microdilution assay method. Compounds 8b, 8f, 8g and 8l inhibited the growth of the H37Rv strain at concentrations of 8 mu g/mL. These compounds (8b, 8f, 8g and 8l) have been further identified as bactericidal and are completely killing the microbes at 32-64 mu g/mL concentrations. Molecular docking studies of the active compounds reveal that these compounds are targeting DprE1 and may act as DprE1 inhibitors. (C) 2014 Elsevier Masson SAS. All rights reserved.