(R)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((Z)-octadec-9-enoylamino)-propionic acid methyl ester | 851588-99-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((Z)-octadec-9-enoylamino)-propionic acid methyl ester
• CAS: 851588-99-3
• 化学式: C₃₄H₅₉NO₄Si
• 分子量: 573.932
• InChiKey: UJUUNVSMRNCQST-AHVPQQLLSA-N

物化性质

• 沸点：
  637.2±55.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.31
• 重原子数：
  40.0
• 可旋转键数：
  21.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((Z)-octadec-9-enoylamino)-propionic acid methyl ester 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 乙醇 为溶剂， 以93%的产率得到(Z)-Octadec-9-enoic acid {(R)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-hydroxymethyl-ethyl}-amide
  参考文献：
  名称：

  [EN] NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR SELECTIVE ANTAGONISTS
  [FR] NOUVEAUX ANTAGONISTES SELECTIFS DU RECEPTEUR DE L'ACIDE LYSOPHOSPHATIDIQUE

  摘要：

  公开号：

  WO2005115150A3
• 作为产物：
  描述：

  D-酪氨酸甲酯盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (R)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((Z)-octadec-9-enoylamino)-propionic acid methyl ester
  参考文献：
  名称：

  Initial structure–activity relationships of lysophosphatidic acid receptor antagonists: discovery of a high-affinity LPA1/LPA3 receptor antagonist

  摘要：

  A recently reported dual LPA(1)/LPA(3) receptor antagonist (VPC12249, 1) has been modified herein so as to optimize potency and selectivity at LPA receptors. Compounds containing variation in the acyl lipid chain and linker region have been synthesized and screened for activity at individual LPA receptors. LPA(1)-selective (14b) and LPA(3)-selective (10g,m) compounds of modest potency have been discovered. Additionally, 2-pyridyl derivative 10t exhibits a K-i value of 18 nM at the LPA(1) receptor and is significantly more potent than 1 at the LPA(3) receptor. This paper describes the synthetic methods, biological evaluation, and structure-activity relationships (SARs) of LPA receptor antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.076

文献信息

• A novel series of 2-pyridyl-containing compounds as lysophosphatidic acid receptor antagonists: development of a nonhydrolyzable LPA3 receptor-selective antagonist
  作者：Brian H Heasley、Renata Jarosz、Karen M Carter、S Jenny Van、Kevin R Lynch、Timothy L Macdonald

  DOI：10.1016/j.bmcl.2004.05.023

  日期：2004.8

  A recently reported dual LPA(1)/LPA(3) receptor antagonist (1) has been modified so as to modulate the basicity, sterics, and dipole moment of the 2-pyridyl moiety. Additionally, the implications of installing nonhydrolyzable phosphate head group isosteres with regard to antagonist potency and selectivity at LPA receptors is described. This study has resulted in the development of the first nonhydrolyzable and presumably phosphatase-resistant LPA(3)-selective antagonist reported to date. (C) 2004 Elsevier Ltd. All rights reserved.