Glyceryl novinamide | 143827-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Glyceryl novinamide
• 英文别名: N-[[4-(2,3-Dihydroxypropoxy)-3-methoxyphenyl]methyl]nonanamide
• CAS: 143827-57-0
• 化学式: C₂₀H₃₃NO₅
• 分子量: 367.486
• InChiKey: IXIJDXIJDOJTTP-UHFFFAOYSA-N

物化性质

• 沸点：
  592.6±50.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香草壬酰胺 、 3-氯-1,2-丙二醇 在 sodium hydroxide 作用下， 反应 1.0h， 以64%的产率得到Glyceryl novinamide
  参考文献：
  名称：

  Hypotensive and antinociceptive effects of ether-linked and relatively non-pungent analogues of N-nonanoyl vanillylamide

  摘要：

  N-nonanoyl vanillylamide (1) is a synthetic substitute of capsaicin (2), a pungent principle in red pepper. 1 was reacted with succinic anhydride, 3-chloro-1,2-propanediol, sodium chloroacetate, and 2-chloroethanol to furnish N-nonanoyl vanillylamide-4-succinyl ester (3), N-nonanoyl vanillylamide-4-glyceryl ether (4), sodium N-nonanoyl vanillylamide-4-0-acetate (5) and N-nonanoyl vanillylamide-4-glycol ether (6), respectively. A 3,4-methylenedioxy derivative of 1, N-nonanoyl piperonylamide (7), was synthesized from piperonylamine HCl and nonanoyl chloride. The ether analogues 4-6 all demonstrated marked antinociceptive and hypotensive effects without producing any overt irritation. In addition, these compounds revealed no untoward vagus reflex or transient hypertensive effect as previously found in 1 or 2.

  DOI：

  10.1016/0223-5234(92)90002-i

文献信息

• ION CHANNEL ACTIVATORS AND METHODS OF USE
  申请人：Flex Pharma, Inc.

  公开号：EP3131541A1

  公开（公告）日：2017-02-22
• US5221692A
  申请人：——

  公开号：US5221692A

  公开（公告）日：1993-06-22
• [EN] METHODS AND FORMULATIIONS OF CAPSAICINOIDS AND CAPSINOIDS<br/>[FR] PROCÉDÉS ET FORMULATIONS DE CAPSAÏCINOÏDES ET CAPSINOÏDES
  申请人：FLEX PHARMA INC

  公开号：WO2015160842A1

  公开（公告）日：2015-10-22

  The present invention relates to compositions of capsaicinoids, capsinoids, or related analogs or combinations thereof, and methods of preparation, formulation, and the medical use of these compositions. In one aspect, the present invention features a composition formulated for oral administration, said composition comprising an effective amount of a capsaicinoid, capsinoid, or related analog or combination thereof.
• [EN] ION CHANNEL ACTIVATORS AND METHODS OF USE<br/>[FR] ACTIVATEURS DES CANAUX IONIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：FLEX PHARMA INC

  公开号：WO2015160843A1

  公开（公告）日：2015-10-22

  The present invention relates to compositions of ion channel activators and methods of preparation, formulation, and the medical use of these compositions. In one aspect, the present invention features a composition formulated for oral administration, said composition comprising an effective amount of an ion channel activator (e.g., a TRPV1 channel activator, a TRPA1 channel activator, an ASIC channel activator, or combination thereof).
• Hypotensive and antinociceptive effects of ether-linked and relatively non-pungent analogues of N-nonanoyl vanillylamide
  作者：IJ Chen、JM Yang、JL Yeh、BN Wu、YC Lo、SJ Chen

  DOI：10.1016/0223-5234(92)90002-i

  日期：1992.4

  N-nonanoyl vanillylamide (1) is a synthetic substitute of capsaicin (2), a pungent principle in red pepper. 1 was reacted with succinic anhydride, 3-chloro-1,2-propanediol, sodium chloroacetate, and 2-chloroethanol to furnish N-nonanoyl vanillylamide-4-succinyl ester (3), N-nonanoyl vanillylamide-4-glyceryl ether (4), sodium N-nonanoyl vanillylamide-4-0-acetate (5) and N-nonanoyl vanillylamide-4-glycol ether (6), respectively. A 3,4-methylenedioxy derivative of 1, N-nonanoyl piperonylamide (7), was synthesized from piperonylamine HCl and nonanoyl chloride. The ether analogues 4-6 all demonstrated marked antinociceptive and hypotensive effects without producing any overt irritation. In addition, these compounds revealed no untoward vagus reflex or transient hypertensive effect as previously found in 1 or 2.