(S)-methyl 2-((2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienamido)-3-phenylpropanoate | 1239492-96-6

• 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: (S)-methyl 2-((2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienamido)-3-phenylpropanoate
• 英文别名: methyl (2S)-2-[[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]amino]-3-phenylpropanoate
• CAS: 1239492-96-6
• 化学式: C₂₂H₂₁NO₅
• 分子量: 379.412
• InChiKey: BRAUMBYHJTYHKU-XVOSZGLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-((2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienamido)-3-phenylpropanoate 在 potassium fluoride on basic alumina 、 盐酸 作用下， 以 水 为溶剂， 以78%的产率得到2-[[(2E, 4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]amino]-3-phenyl-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：

  胡椒碱 在 甲醇 、 硼酸 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 (S)-methyl 2-((2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienamido)-3-phenylpropanoate
  参考文献：
  名称：

  胡椒碱-氨基酸酯缀合物的合成及其对人癌细胞系的细胞毒活性研究

  摘要：

  摘要在温和的条件下合成了一系列胡椒碱-氨基酸酯结合物（4a - 4r），并筛选了它们对一组人类癌细胞系（IMR-32，MCF-7，PC-3，DU-145， Colo-205和Hep-2）。亲本化合物胡椒碱缺乏显着活性，但类似物对所有测试的人类癌细胞系均有效。通过肽键将d-和l-氨基酸侧链引入胡椒碱显着增加了细胞毒活性。在测试的缀合物中，4p对具有IC 50的DU-145细胞系显示出显着的细胞毒活性为21μM。合成方案适合于产生具有各种结构基序的胡椒碱衍生物，以探索所需的活性。 图形概要在温和的条件下合成了一系列胡椒碱-氨基酸酯缀合物（4a - 4r），并筛选了它们对一组人类癌细胞系（IMR-32，MCF-7，PC-3，DU-145， Colo-205和Hep-2）。

  DOI：

  10.1007/s00044-010-9500-5

文献信息

• Synthesis of piperine–amino acid ester conjugates and study of their cytotoxic activities against human cancer cell lines
  作者：V. Rama Subba Rao、G. Suresh、R. Ranga Rao、K. Suresh Babu、G. Chashoo、A. K. Saxena、J. Madhusudana Rao

  DOI：10.1007/s00044-010-9500-5

  日期：2012.1

  piperine–amino acid ester conjugates (4a–4r) were synthesized under mild conditions and screened for their cytotoxic activities against a panel of human cancer cell lines (IMR-32, MCF-7, PC-3, DU-145, Colo-205, and Hep-2). The parent compound piperine lacked significant activity but the analogues were effective to in all tested human cancer cell lines. The introduction of d- and l-amino acid side chain

  摘要在温和的条件下合成了一系列胡椒碱-氨基酸酯结合物（4a - 4r），并筛选了它们对一组人类癌细胞系（IMR-32，MCF-7，PC-3，DU-145， Colo-205和Hep-2）。亲本化合物胡椒碱缺乏显着活性，但类似物对所有测试的人类癌细胞系均有效。通过肽键将d-和l-氨基酸侧链引入胡椒碱显着增加了细胞毒活性。在测试的缀合物中，4p对具有IC 50的DU-145细胞系显示出显着的细胞毒活性为21μM。合成方案适合于产生具有各种结构基序的胡椒碱衍生物，以探索所需的活性。 图形概要在温和的条件下合成了一系列胡椒碱-氨基酸酯缀合物（4a - 4r），并筛选了它们对一组人类癌细胞系（IMR-32，MCF-7，PC-3，DU-145， Colo-205和Hep-2）。
• 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.