2-(4-tert-butylbenzyl)-3-[2-(4-amino-3,5-dibromophenyl)acetamido]propyl pivalate | 1258845-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-tert-butylbenzyl)-3-[2-(4-amino-3,5-dibromophenyl)acetamido]propyl pivalate
• 英文别名: [2-[[[2-(4-amino-3,5-dibromophenyl)acetyl]amino]methyl]-3-(4-tert-butylphenyl)propyl] 2,2-dimethylpropanoate
• CAS: 1258845-88-3
• 化学式: C₂₇H₃₆Br₂N₂O₃
• 分子量: 596.402
• InChiKey: RPJVAQLXHXMPQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4-amino-3,5-dibromophenyl)acetic acid 、 N-[2-(4-tert-butylbenzyl)-3-pivaloyloxy-propyl]hydroxylamine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以86%的产率得到2-(4-tert-butylbenzyl)-3-[2-(4-amino-3,5-dibromophenyl)acetamido]propyl pivalate
  参考文献：
  名称：

  Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3-methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with K-i (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6'-iodononivamide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.001