5-(3,4-methylenedioxyphenyl)pentanoic acid N-isobutylamide | 5950-13-0

• 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-methylenedioxyphenyl)pentanoic acid N-isobutylamide
• 英文别名: Piperamide-B5:0；5-benzo[1,3]dioxol-5-yl-pentanoic acid isobutylamide；Tetrahydropiperlonguminin；N-(2-Methylpropyl)-1,3-benzodioxole-5-pentanamide；5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)pentanamide
• CAS: 5950-13-0
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: LOPLZZILUGYJAW-UHFFFAOYSA-N

物化性质

• 熔点：
  66 °C
• 沸点：
  462.4±24.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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 sodium hydroxide 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、441.27 kPa 条件下， 反应 5.75h， 生成 5-(3,4-methylenedioxyphenyl)pentanoic acid N-isobutylamide
  参考文献：
  名称：

  Nakamura, Norio; Kiuchi, Fumiyuki; Tsuda, Yoshisuke, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 7, p. 2647 - 2651

  摘要：

  DOI：

文献信息

• Crude Drugs Effective on Visceral Larva Migrans. Part XVIII. Synthesis and Nematocidal Activity of Aralkyl- and Aralkenylamides Related to Piperamide on Second-Stage Larvae of Toxocara canis.
  作者：Fumiyuki KIUCHI、Norio NAKAMURA、Makiko SAITOH、Kazue KOMAGOME、Hirokuni HIRAMATSU、Noriaki TAKIMOTO、Nobuaki AKAO、Kaoru KONDO、Yoshisuke TSUDA

  DOI：10.1248/cpb.45.685

  日期：——

  piperamides (3,4-methylenedioxyphenyl homologues) showed the strongest activity among the homologues tested, methoxy substituent(s) on the aromatic ring did not have much effect on the activity. However, conversion of the methoxy group to a hydroxy group greatly decreased the activity and shortened the chain length giving the strongest activity. Calculated log P values of non-phenolic aryl-piperamides fell

  合成了与哌啶相关的79个芳烷基和芳烯基酰胺，并研究了它们对犬round虫Toxocara canis的第二级幼虫的杀线虫活性。活性很大程度上取决于烷基链的长度和胺部分的性质，但是几乎不受链中是否存在双键的影响。在一系列同系物中表现出最强活性的烷基链长，对于吡咯烷酰胺为m = 11，对于N-甲基哌嗪酰胺为m = 13。尽管在所测试的同系物中，哌啶（3，4-亚甲基二氧苯基同系物）显示出最强的活性，但是芳环上的甲氧基取代基对该活性没有太大影响。然而，甲氧基向羟基的转化大大降低了活性并缩短了链长，从而提供了最强的活性。计算出的非酚芳基哌啶的log P值在3.5至4.5范围内，而羟苯基哌啶的log P值较小，表明酚和非酚化合物的杀线活性涉及不同的机理。
• Piperine analogs as potent Staphylococcus aureus NorA efflux pump inhibitors
  作者：Payare L. Sangwan、Jawahir L. Koul、Surrinder Koul、Mallepally V. Reddy、Niranjan Thota、Inshad A. Khan、Ashwani Kumar、Nitin P. Kalia、Ghulam N. Qazi

  DOI：10.1016/j.bmc.2008.09.042

  日期：2008.11

  Based on our recent findings that piperine is a potent Staphylococcus aureus NorA efflux pump inhibitor (EPI), 38 piperine analogs were synthesized and bioevaluated for their EPI activity. Twenty-five of them were found active with potentiating activity equivalent or more than known EPIs like reserpine, carsonic acid and verapamil. The inhibitory mechanism of the compounds was confirmed by efflux inhibition assay using ethidium bromide as NorA substrate. The present communication describes the synthesis, bioevaluation and structure related activity of these efflux pump inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.
• Adesina; Adebayo; Adesina, Pharmazie, 2002, vol. 57, # 9, p. 622 - 627
  作者：Adesina、Adebayo、Adesina、Groening

  DOI：——

  日期：——
• AROMATIC ALKENOIC ACID DERIVATIVES
  申请人：Symrise AG

  公开号：US20150259319A1

  公开（公告）日：2015-09-17

  What are proposed are primarily aromatic alkenoic acid derivatives of the formula I for use in a therapeutic method as (a) means for reducing appetite and/or (b) means for causing a feeling of satiation and/or as (c) means for reducing energy intake and/or as (d) mood enhancers, and the non-therapeutic use of the aromatic alkenoic acid derivatives of formula I as (a) means for reducing appetite and/or (b) means for causing a feeling of satiation and/or as (c) means for reducing energy intake and/or as (d) mood enhancers.