piperic acid mesylate | 700359-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: piperic acid mesylate
• CAS: 700359-91-7
• 化学式: C₁₃H₁₂O₆S
• 分子量: 296.301
• InChiKey: AFAOODAEKSJHJR-ZUVMSYQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  piperic acid mesylate 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 4.0h， 生成 5-(3,4-methylenedioxy phenyl)-pentanoic acid cyclohexyl amide
  参考文献：
  名称：

  Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation

  摘要：

  A wide range of piperine analogues has been synthesised in order to undertake a structure-activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential for this activity. A number of highly active piperine analogues have been identified, for instance 1-(3,4-methylenedioxyphenyl)-penta-2E,4E-dienoic acid methyl ester (3a), 1-E,E-piperinoyl-isobutylamine (4f) and 1-(3,4-methylenedioxyphenyl)-pentanoic acid cyclohexyl amide (20). A selection of analogues has also been evaluated for their effect on melanocyte morphology and melanogenesis. The piperine analogues altered cell morphology by increasing dendrite formation leading to bi-, tri- and quadripolar cells. These same analogues were found to increase total melanin in cell cultures, although melanin content per cell was not significantly altered from control in the presence of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.036
• 作为产物：
  描述：

  胡椒碱 在 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 93.0h， 生成 piperic acid mesylate
  参考文献：
  名称：

  Disruption of redox homeostasis with synchronized activation of apoptosis highlights the antifilarial efficacy of novel piperine derivatives: An in vitro mechanistic approach

  摘要：

  DOI：

  10.1016/j.freeradbiomed.2021.04.026

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.