N-(3-hydroxypropionyl)hexadecananamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(3-hydroxypropionyl)hexadecananamide
• 英文别名: N-(3-hydroxypropanoyl)hexadecanamide
• 化学式: C₁₉H₃₇NO₃
• 分子量: 327.508
• InChiKey: NWJBJUZMWBPJRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  十六胺 、 3-羟基丙酸 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.67h， 以42%的产率得到N-(3-hydroxypropionyl)hexadecananamide
  参考文献：
  名称：

  Development of new inhibitors for N-acylethanolamine-hydrolyzing acid amidase as promising tool against bladder cancer

  摘要：

  The endocannabinoid system is a signaling system involved in a wide range of biological effects. Literature strongly suggests the endocannabinoid system role in the pathogenesis of cancer and that its pharmacological activation produces therapeutic benefits. Last research promotes the endocannabinoid system modulation by inhibition of endocannabinoids hydrolytic enzymes instead of direct activation of endocannabinoid receptors to avoid detrimental effects on cognition and motor control. Here we report the identification of N-acylethanolamine-hydrolyzing acid amidase (NAAA) inhibitors able to reduce cell proliferation and migration and cause cell death on different bladder cancer cell lines. These molecules were designed, synthesized and characterized and active compounds were selected by a fluorescence high-throughput screening method set-up on human recombinant NAAA that also allows to characterize the mechanism of inhibition. Together our results suggest an important role for NAAA in cell migration and in inducing tumor cell death promoting this enzyme as pharmacological target against bladder cancer. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.12.042

文献信息

• OMEGA-CYCLOHEXYLALKAN-1-OLES AND USE THEREOF AS ANTIMICROBIAL ACTIVES TO COMBAT BODY ODOR
  申请人：Symrise AG

  公开号：EP2424829B1

  公开（公告）日：2015-01-07
• [EN] OMEGA-CYCLOHEXYLALKAN-1-OLES AND USE THEREOF AS ANTIMICROBIAL ACTIVES TO COMBAT BODY ODOR<br/>[FR] OMÉGA-CYCLOHEXYLALCAN-1-OLES ET LEUR UTILISATION COMME ANTIMICROBIENS ACTIFS POUR LUTTER CONTRE LES ODEURS CORPORELLES
  申请人：SYMRISE GMBH & CO KG

  公开号：WO2009101216A2

  公开（公告）日：2009-08-20

  The present invention relates to antimicrobially active ω-cyclohexylalkan-1-oles of the following Formula (I), to a method for producing said compounds and to the use thereof as antimicrobial agents for treating body odor, wherein R1 to R6 independently of one another denote hydrogen or a linear or branched alkyl radical having 1 to 12 carbon atoms, Ra and Rb independently of one another denote hydrogen, a linear or branched alkyl radical having 1 to 6 carbon atoms or a linear or branched alkoxyradical having 1 to 4 carbon atoms, and x is 0 or 1, wherein preferably the total number of carbon atoms in R1 to R6 is 18 or less.