5-(3,4-methylenedioxy phenyl)-pentanoic acid cyclohexyl amide

• 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: 5-(3,4-methylenedioxy phenyl)-pentanoic acid cyclohexyl amide
• 英文别名: 5-(3,4-Methylenedioxy phenyl)-pentanoic acid cyclohexylamide；5-(1,3-benzodioxol-5-yl)-N-cyclohexylpentanamide
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: ZNIBAGOSRYBJPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  胡椒碱 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 6.5h， 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

文献信息

• Treatment of skin conditions
  申请人：BTG International Limited

  公开号：US20020168369A1

  公开（公告）日：2002-11-14

  The present invention provides piperine and analogues or derivatives thereof for the treatment of skin conditions treatable by stimulation of melanocyte proliferation, such as vitiligo, and also for treating skin cancer. The piperine and analogues or derivatives thereof may also be used to cosmetically promote or enhance the natural coloration of the skin.

  本发明提供了辣椒碱及其类似物或衍生物，用于治疗可通过刺激黑色素细胞增殖来治疗的皮肤状况，如白癜风，并且用于治疗皮肤癌。辣椒碱及其类似物或衍生物也可用于美容促进或增强皮肤的自然着色。
• Compounds for use in the treatment of skin conditions
  申请人：——

  公开号：US20040254165A1

  公开（公告）日：2004-12-16

  The present invention provides compounds of formula (I) and analogues or derivatives thereof for the treatment of skin conditions, such as Vitiligo, which are treatable by the stimulation of melanocyte proliferation and also for treating skin cancer. The compounds may also be used to cosmetically enhance the natural coloration of the skin. 1

  本发明提供了式（I）化合物及其类似物或衍生物，用于治疗可通过刺激黑色素细胞增殖治疗的皮肤病症，例如白癜风，并用于治疗皮肤癌。这些化合物还可用于美容，增强皮肤的自然色彩。
• COMPOUNDS FOR USE IN THE TREATMENT OF SKIN CONDITIONS
  申请人：BTG INTERNATIONAL LIMITED

  公开号：EP1377571A1

  公开（公告）日：2004-01-07
• US6680391B2
  申请人：——

  公开号：US6680391B2

  公开（公告）日：2004-01-20
• US7122561B2
  申请人：——

  公开号：US7122561B2

  公开（公告）日：2006-10-17