N-isobutyl-9-(3,4-methylenedioxyphenyl)nonanamide | 83029-42-9

• 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: N-isobutyl-9-(3,4-methylenedioxyphenyl)nonanamide
• 英文别名: hexahydroretrofractamide A；1,3-Benzodioxole-5-nonanamide, N-(2-methylpropyl)-；9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nonanamide
• CAS: 83029-42-9
• 化学式: C₂₀H₃₁NO₃
• 分子量: 333.471
• InChiKey: GNOSQACJJSYDEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  9'-(3,4-methylenedioxy-phenyl)-nonanoic acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 N-isobutyl-9-(3,4-methylenedioxyphenyl)nonanamide
  参考文献：
  名称：

  在犬第二代幼虫中与哌酰胺有关的芳烷基和芳烯基酰胺的合成和杀线活性。

  摘要：

  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。

  DOI：

  10.1248/cpb.45.685

文献信息

• Structural and synthetic studies on the retrofractamides—amide constituents of Piper retrofractum
  作者：Avijit Banerji、Debabrata Bandyopadhyay、Manjusha Sarkar、Arup K. Siddhanta、Sudhir C. Pal、Somnath Ghosh、Koshy Abraham、James N. Shoolery

  DOI：10.1016/s0031-9422(00)83537-2

  日期：1985.2

  C, were isolated from the total above-ground parts of Piper retrofractum . Retrofractamide A was shown to be N -isobutyl-9(3′,4′-methylenedioxyphenyl)2 E ,4 E ,8 E -nonatrienamide from spectroscopic and chemical investigations. The structure 6 for retrofractamide C was suggested from spectroscopic and chemical studies and was confirmed by a total stereoselective synthesis. The presence of sesamin and

  摘要 从Piper retrofractum 的全部地上部分分离得到两种新的不饱和酰胺，retrofractamides A 和C。光谱和化学研究表明 Retrofractamide A 是 N-isobutyl-9(3',4'-methylenedioxyphenyl)2 E,4 E,8 E-nonatrienamide。反曲霉胺 C 的结构 6 是从光谱和化学研究中提出的，并通过全立体选择性合成得到证实。芝麻素和3,4,5-三甲氧基二氢肉桂酸以及retrofractamide A 的两个高级同系物的存在，即。证明了哌啶（retrofractamide B）和retrofractamide D。也实现了哌啶的合成。
• Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells
  作者：Ahmed Aboul-Fotouh Mourad、Seikou Nakamura、Tsubasa Ueno、Takahiro Minami、Takanari Yagi、Haruka Yasue、Ryoko Komatsu、Masayuki Yoshikawa、Ashraf Mohamed Taye、Mohamed Ahmed El-Moselhy、Mohamed Montaser Khalifa、Hisashi Matsuda

  DOI：10.1016/j.bmcl.2013.06.101

  日期：2013.9

  In a previous study, retrofractamide A from the fruit of Piper chaba was shown to promote adipogenesis in 3T3-L1 cells. In the present study, retrofractamide A and its derivatives were synthesized, and their adipogenetic effects in 3T3-L1 cells were examined. Among the tested compounds, an amide composed of 9-(3',4'-methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid and an n-butyl or n-pentyl amine showed strongest activity. Moreover, the amide with the n-pentyl amine moiety significantly increased the uptake of 2-deoxyglucose into the cells, and also increased the mRNA levels of adiponectin, peroxisome proliferator-activated receptor gamma 2 (PPAR gamma 2), glucose transporter 4 (GLUT4), fatty acid-binding protein (aP2), and CCAAT/enhancer-binding protein (C/EBP) alpha and beta in a similar manner as the PPAR gamma agonist troglitazone, although it had less agonistic activity against PPAR gamma. (C) 2013 Elsevier Ltd. All rights reserved.
• Pring, Brian G., Journal of the Chemical Society. Perkin transactions I, 1982, p. 1493 - 1498
  作者：Pring, Brian G.

  DOI：——

  日期：——
• 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。