methyl (2S)-2-[[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]amino]-3-(1H-indol-3-yl)propanoate | 1239493-03-8

• 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: methyl (2S)-2-[[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 1239493-03-8
• 化学式: C₂₄H₂₂N₂O₅
• 分子量: 418.449
• InChiKey: SXIIKHLIAMPADS-DBLONPDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]amino]-3-(1H-indol-3-yl)propanoate 在 potassium fluoride on basic alumina 、 盐酸 作用下， 以 水 为溶剂， 以76%的产率得到2-[[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]amino]-3-(1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  Synthesis and Antileishmanial activity of Piperoyl-Amino Acid Conjugates

  摘要：

  Based on reported antileishmanial activity of naturally occurring alkaloid piperine and amino acid esters, their conjugates were synthesized by the hydrolysis of piperine to piperic acid followed by reaction with amino acid methyl esters. These conjugates were further converted to compounds with free carboxyl group and those with reduced double bonds. The synthesized compounds were evaluated for activity against promastigote and amastigote forms of L. donovani in vitro. All the compounds showed better activity than either piperine or the amino acid methyl esters. Piperoyl-valine methyl ester was the most active compound showing an IC(50) of 0.075 mM against the amastigotes. Two active compounds were evaluated for in vivo activity in golden hamster model of leishmaniasis. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.033
• 作为产物：
  描述：

  L-色氨酸甲酯 、 piperic acid mesylate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S)-2-[[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]amino]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Synthesis and Antileishmanial activity of Piperoyl-Amino Acid Conjugates

  摘要：

  Based on reported antileishmanial activity of naturally occurring alkaloid piperine and amino acid esters, their conjugates were synthesized by the hydrolysis of piperine to piperic acid followed by reaction with amino acid methyl esters. These conjugates were further converted to compounds with free carboxyl group and those with reduced double bonds. The synthesized compounds were evaluated for activity against promastigote and amastigote forms of L. donovani in vitro. All the compounds showed better activity than either piperine or the amino acid methyl esters. Piperoyl-valine methyl ester was the most active compound showing an IC(50) of 0.075 mM against the amastigotes. Two active compounds were evaluated for in vivo activity in golden hamster model of leishmaniasis. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.033

文献信息

• Synthesis and Antileishmanial activity of Piperoyl-Amino Acid Conjugates
  作者：Inder Pal Singh、Shreyans Kumar Jain、Amandeep Kaur、Sukhvinder Singh、Rajender Kumar、Prabha Garg、Shyam Sundar Sharma、Sunil Kumar Arora

  DOI：10.1016/j.ejmech.2010.04.033

  日期：2010.8

  Based on reported antileishmanial activity of naturally occurring alkaloid piperine and amino acid esters, their conjugates were synthesized by the hydrolysis of piperine to piperic acid followed by reaction with amino acid methyl esters. These conjugates were further converted to compounds with free carboxyl group and those with reduced double bonds. The synthesized compounds were evaluated for activity against promastigote and amastigote forms of L. donovani in vitro. All the compounds showed better activity than either piperine or the amino acid methyl esters. Piperoyl-valine methyl ester was the most active compound showing an IC(50) of 0.075 mM against the amastigotes. Two active compounds were evaluated for in vivo activity in golden hamster model of leishmaniasis. (C) 2010 Elsevier Masson SAS. All rights reserved.