1-(1H-indol-3-yl)-2-(piperidin-1-yl)ethane-1,2-dione | 92579-89-0

• 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-(piperidin-1-yl)ethane-1,2-dione
• 英文别名: 1-(1H-Indol-3-yl)-2-piperidin-1-yl-ethane-1,2-dione；1-(1H-indol-3-yl)-2-piperidin-1-ylethane-1,2-dione
• CAS: 92579-89-0
• 化学式: C₁₅H₁₆N₂O₂
• mdl: MFCD00433590
• 分子量: 256.304
• InChiKey: RZQPAQOFGPUUOC-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C
• 沸点：
  461.7±37.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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-(piperidin-1-yl)ethane-1,2-dione 在 4-二甲氨基吡啶 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 3-(3-(2-oxo-2-(piperidin-1-yl)acetyl)-1H-indol-1-yl)-N-(4-phenylthiazol-2-yl)propanamide
  参考文献：
  名称：

  噻唑连接的吲哚基-3-乙醛酰胺衍生物作为微管蛋白聚合抑制剂的合成

  摘要：

  合成了一系列噻唑连接的吲哚基-3-乙二醛酰胺衍生物，并通过使用评估了它们对DU145（前列腺），PC-3（前列腺），A549（肺）和HCT-15（结肠）癌细胞系的体外细胞毒活性。 3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物（MTT）测定。在所有合成的化合物中，化合物13d 对DU145癌细胞系的IC 50为93 nM。还对RWPE-1细胞测试了活性最高的化合物13d，与DU145细胞相比，它是安全的。还评估了目标化合物对微管蛋白聚合的抑制活性。此外，化合物13d的处理对DU145细胞的抑制导致细胞迁移能力的抑制。studies啶橙/溴化乙锭（AO / EB），DAPI，膜联蛋白V-FITC /碘化丙锭染色等详细研究表明，化合物13d诱导DU145细胞凋亡。在DU145细胞系上评估了细胞毒性化合物13d对细胞周期分布的影响，表现出在G2 / M期的细胞周期停滞。另外，用化合

  DOI：

  10.1016/j.ejmech.2017.06.025
• 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-(piperidin-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

• Untersuchungen �ber Rauwolfia-Alkaloid-Modelle I
  作者：Thomas N�gr�di

  DOI：10.1007/bf00905400

  日期：——
• 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.
• Synthesis and biological activity of novel mono-indole and mono-benzofuran inhibitors of bacterial transcription initiation complex formation
  作者：Marcin Mielczarek、Ruth V. Thomas、Cong Ma、Hakan Kandemir、Xiao Yang、Mohan Bhadbhade、David StC. Black、Renate Griffith、Peter J. Lewis、Naresh Kumar

  DOI：10.1016/j.bmc.2015.02.037

  日期：2015.4

  Our ongoing research focused on targeting transcription initiation in bacteria has resulted in synthesis of several classes of mono-indole and mono-benzofuran inhibitors that targeted the essential protein-protein interaction between RNA polymerase core and sigma(70)/sigma(A) factors in bacteria. In this study, the reaction of indole-2-, indole-3-, indole-7- and benzofuran-2-glyoxyloyl chlorides with amines and hydrazines afforded a variety of glyoxyloylamides and glyoxyloylhydrazides. Similarly, condensation of 2- and 7-trichloroacetylindoles with amines and hydrazines delivered amides and hydrazides. The novel molecules were found to inhibit the RNA polymerase-sigma(70)/sigma(A) interaction as measured by ELISA, and also inhibited the growth of both Gram-positive and Gram-negative bacteria in culture. Structure-activity relationship (SAR) studies of the mono-indole and mono-benzofuran inhibitors suggested that the hydrophilic-hydrophobic balance is an important determinant of biological activity. (C) 2015 Elsevier Ltd. All rights reserved.
• ENV POLYPEPTIDE COMPLEXES AND METHODS OF USE
  申请人：Novartis Vaccines and Diagnostics, Inc.

  公开号：EP1773880A2

  公开（公告）日：2007-04-18
• EP1773880A4
  申请人：——

  公开号：EP1773880A4

  公开（公告）日：2009-09-09