3-(1H-indol-3-yl)-2-[2-(1H-indol-3-yl)-2-oxo-acetylamino]propionic acid methyl ester | 1257308-32-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(1H-indol-3-yl)-2-[2-(1H-indol-3-yl)-2-oxo-acetylamino]propionic acid methyl ester
• 英文别名: methyl (2R)-3-(1H-indol-3-yl)-2-[[2-(1H-indol-3-yl)-2-oxoacetyl]amino]propanoate
• CAS: 1257308-32-9
• 化学式: C₂₂H₁₉N₃O₄
• 分子量: 389.411
• InChiKey: HIFDOUATSGPYEI-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1H-indol-3-yl)-2-[2-(1H-indol-3-yl)-2-oxo-acetylamino]propionic acid methyl ester 在 水 、 氯甲酸乙酯 、 sodium hydride 、 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 0.5h， 生成 2-[[(2R)-3-(1H-indol-3-yl)-2-[[2-[1-(4-methylphenyl)sulfonylindol-3-yl]-2-oxoacetyl]amino]propanoyl]amino]acetic acid
  参考文献：
  名称：

  Indole based peptidomimetics as anti-inflammatory and anti-hyperalgesic agents: Dual inhibition of 5-LOX and COX-2 enzymes

  摘要：

  The indoles bearing a tosyl group at N-1 and a dipeptide substituent at C-3 were screened for anti-inflammatory and anti-hyperalgesic activities. Some of the compounds made significant reduction in the dextran induced swelling and capsaicin induced pain in the albino mice. About 95% reversal in capsaicin induced pain occurred in the presence of 5 mg kg(-1) of compound 7b, 7d and 7h while diclofenac showed 90% reversal when its 10 mg kg(-1) dose was used. In order to examine the mode of action of these compounds; COX-1, COX-2 and 5-LOX enzyme immunoassays were performed. The IC50 of compound 7b for COX-2 and 5-LOX were in the nM range: 5-LOX, IC50 = 2.0 nM; COX-2, IC50 = 6.3 nM, selectivity for COX-2 over COX-1 was 351. The interactions of the compounds with COX-2 and 5-LOX were supported by the physical parameters including K-i, K-a and Delta G. The most potent compounds 7b, 7d and 7h showed no toxicity to the animals and were identified as the promising leads for anti-inflammatory drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.044
• 作为产物：
  描述：

  吲哚 在 potassium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 3-(1H-indol-3-yl)-2-[2-(1H-indol-3-yl)-2-oxo-acetylamino]propionic acid methyl ester
  参考文献：
  名称：

  Indole based peptidomimetics as anti-inflammatory and anti-hyperalgesic agents: Dual inhibition of 5-LOX and COX-2 enzymes

  摘要：

  The indoles bearing a tosyl group at N-1 and a dipeptide substituent at C-3 were screened for anti-inflammatory and anti-hyperalgesic activities. Some of the compounds made significant reduction in the dextran induced swelling and capsaicin induced pain in the albino mice. About 95% reversal in capsaicin induced pain occurred in the presence of 5 mg kg(-1) of compound 7b, 7d and 7h while diclofenac showed 90% reversal when its 10 mg kg(-1) dose was used. In order to examine the mode of action of these compounds; COX-1, COX-2 and 5-LOX enzyme immunoassays were performed. The IC50 of compound 7b for COX-2 and 5-LOX were in the nM range: 5-LOX, IC50 = 2.0 nM; COX-2, IC50 = 6.3 nM, selectivity for COX-2 over COX-1 was 351. The interactions of the compounds with COX-2 and 5-LOX were supported by the physical parameters including K-i, K-a and Delta G. The most potent compounds 7b, 7d and 7h showed no toxicity to the animals and were identified as the promising leads for anti-inflammatory drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.044

文献信息

• Synthesis and biological evaluation of indolyl glyoxylamides as a new class of antileishmanial agents
  作者：Shikha S. Chauhan、Leena Gupta、Monika Mittal、Preeti Vishwakarma、Suman Gupta、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2010.08.119

  日期：2010.11

  A series of indolylglyoxylamide derivatives have been synthesized and evaluated in vitro against amastigote form of Leishmania donovani. Compound 8c has been identified as the most active analog of the series with IC(50) value of 5.17 mu M and SI value of 31.48, and is several folds more potent than the standard drugs sodium stilbogluconate and pentamidine. (C) 2010 Elsevier Ltd. All rights reserved.
• Indole based peptidomimetics as anti-inflammatory and anti-hyperalgesic agents: Dual inhibition of 5-LOX and COX-2 enzymes
  作者：Palwinder Singh、Parteek Prasher、Parvirti Dhillon、Rajbir Bhatti

  DOI：10.1016/j.ejmech.2015.04.044

  日期：2015.6

  The indoles bearing a tosyl group at N-1 and a dipeptide substituent at C-3 were screened for anti-inflammatory and anti-hyperalgesic activities. Some of the compounds made significant reduction in the dextran induced swelling and capsaicin induced pain in the albino mice. About 95% reversal in capsaicin induced pain occurred in the presence of 5 mg kg(-1) of compound 7b, 7d and 7h while diclofenac showed 90% reversal when its 10 mg kg(-1) dose was used. In order to examine the mode of action of these compounds; COX-1, COX-2 and 5-LOX enzyme immunoassays were performed. The IC50 of compound 7b for COX-2 and 5-LOX were in the nM range: 5-LOX, IC50 = 2.0 nM; COX-2, IC50 = 6.3 nM, selectivity for COX-2 over COX-1 was 351. The interactions of the compounds with COX-2 and 5-LOX were supported by the physical parameters including K-i, K-a and Delta G. The most potent compounds 7b, 7d and 7h showed no toxicity to the animals and were identified as the promising leads for anti-inflammatory drugs. (C) 2015 Elsevier Masson SAS. All rights reserved.