tetradecanoyl bromide | 83228-43-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: tetradecanoyl bromide
• 英文别名: n-Tetradecanoyl bromide
• CAS: 83228-43-7
• 化学式: C₁₄H₂₇BrO
• 分子量: 291.272
• InChiKey: PYLHQFUYUMDOMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tetradecanoyl bromide 、 N-6 benzyl-L-lysine 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以82%的产率得到N-2-tetradecanoyl-N'-6-benzyl-L-lysine
  参考文献：
  名称：

  化合物N-2-烷酰基-N-6-苄基-L-赖氨酸及其合成方法

  摘要：

  本发明涉及一种新的化合物N‑2‑烷酰基‑N‑6‑苄基‑L‑赖氨酸(以下简称化合物1)及其合成方法。本发明提供了从丁酰基，戊酰基，直到二十烷酰基等一系列的N‑2‑烷酰基‑N‑6‑苄基‑L‑赖氨酸化合物。结构式如式(3)所示化合物N‑2‑烷酰基‑N‑6‑苄基‑L‑赖氨酸：其中n＝0～18的直链烷基。

  公开号：

  CN109704986A

文献信息

• The cationic amphiphile 3,4-bis(tetradecyloxy)benzylamine inhibits LPS signaling by competing with endotoxin for CD14 binding
  作者：Matteo Piazza、Valentina Calabrese、Chiara Baruffa、Theresa Gioannini、Jerrold Weiss、Francesco Peri

  DOI：10.1016/j.bcp.2010.06.019

  日期：2010.12

  The identification of the bacterial endotoxin receptors for innate immunity, most notably the Toll-like receptor 4 (TLR4), has sparked great interest in therapeutic manipulation of innate immune system. We have recently developed synthetic molecules that have been shown to inhibit TLR4 activation in vitro and in vivo. Here we present the synthesis and the biological characterization of a new molecule, the cationic amphiphile 3,4-bis(tetradecyloxy)benzylamine, with a structure strictly related to the previously developed TLR4 modulators. This compound is able to inhibit in a dose-dependent manner the LPS-stimulated TLR4 activation in HEK cells. In order to characterize the mechanism of action of this compound, we investigated possible interactions with the extracellular components that bind and shuttle LPS to TLR4, namely LBP, CD14, and MD-2. This compound inhibited LBP/CD14-dependent LPS transfer to MD-2.TLR4, resulting in reduced formation of a (LPS-MD-2-TLR4)(2) complex. This effect was due to inhibition of the transfer of LPS from aggregates in solution to sCD14 with little or no effect on LPS shuttling from LPS/CD14 to MD-2. This compound also inhibited transfer of LPS monomer from full-length CD14 to a truncated, polyhistidine tagged CD14. Taken together, our findings strongly suggest that this compound inhibits LPS-stimulated TLR4 activation by competitively occupying CD14 and thereby reducing the delivery of activating endotoxin to MD-2.TLR4. (C) 2010 Elsevier Inc. All rights reserved.
• US4614546A
  申请人：——

  公开号：US4614546A

  公开（公告）日：1986-09-30
• 化合物N-2-烷酰基-N-6-苄基-L-赖氨酸及其合成方法
  申请人：浙江华贝药业有限责任公司

  公开号：CN109704986A

  公开（公告）日：2019-05-03

  本发明涉及一种新的化合物N‑2‑烷酰基‑N‑6‑苄基‑L‑赖氨酸(以下简称化合物1)及其合成方法。本发明提供了从丁酰基，戊酰基，直到二十烷酰基等一系列的N‑2‑烷酰基‑N‑6‑苄基‑L‑赖氨酸化合物。结构式如式(3)所示化合物N‑2‑烷酰基‑N‑6‑苄基‑L‑赖氨酸：其中n＝0～18的直链烷基。