N-[2-(4-tert-butylbenzyl)-3-(pivaloyloxy)propyl]-2-[4-(2-bromoethoxy)-3-methoxyphenyl]acetamide | 289903-44-2

• 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: N-[2-(4-tert-butylbenzyl)-3-(pivaloyloxy)propyl]-2-[4-(2-bromoethoxy)-3-methoxyphenyl]acetamide
• 英文别名: 2,2-Dimethyl-propionic Acid 2-({2-[4-(2-Bromoethoxy)-3-methoxyphenyl]acetylamino}methyl)-3-(4-t-butylphenyl)propyl Ester；[2-[[[2-[4-(2-Bromoethoxy)-3-methoxyphenyl]acetyl]amino]methyl]-3-(4-tert-butylphenyl)propyl] 2,2-dimethylpropanoate
• CAS: 289903-44-2
• 化学式: C₃₀H₄₂BrNO₅
• 分子量: 576.571
• InChiKey: LTSCJMLZVKHTDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(4-tert-butylbenzyl)-3-(pivaloyloxy)propyl]-2-[4-(2-bromoethoxy)-3-methoxyphenyl]acetamide 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以92%的产率得到N-[2-(4-tert-butylbenzyl)-3-(pivaloyloxy)propyl]-2-[4-(2-azidoethoxy)-3-methoxyphenyl]acetamide
  参考文献：
  名称：

  Phenolic Modification as an Approach to Improve the Pharmacology of the 3-Acyloxy-2-benzylpropyl Homovanillic Amides and Thioureas, a Promising Class of Vanilloid Receptor Agonists and Analgesics

  摘要：

  In order to improve the analgesic activity and pharmacokinetics of thioureas 2 and 3, which we previously developed as potent vanilloid receptor (VR) agonists, we prepared and characterized phenolic modifications of them and of their amide surrogates (7, 8). The aminoethyl analogue of the amide template 13 was a potent analgesic with an EC50 = 0.96 mug/kg in the AA-induced writhing test and with better in vivo stability than the parent phenol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00387-x
• 作为产物：
  描述：

  3-azido-2-(4-t-butylbenzyl)propyl pivalate 在 palladium on activated charcoal 氢氧化钾 、 四丁基氢氧化铵 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 N-[2-(4-tert-butylbenzyl)-3-(pivaloyloxy)propyl]-2-[4-(2-bromoethoxy)-3-methoxyphenyl]acetamide
  参考文献：
  名称：

  Phenolic Modification as an Approach to Improve the Pharmacology of the 3-Acyloxy-2-benzylpropyl Homovanillic Amides and Thioureas, a Promising Class of Vanilloid Receptor Agonists and Analgesics

  摘要：

  In order to improve the analgesic activity and pharmacokinetics of thioureas 2 and 3, which we previously developed as potent vanilloid receptor (VR) agonists, we prepared and characterized phenolic modifications of them and of their amide surrogates (7, 8). The aminoethyl analogue of the amide template 13 was a potent analgesic with an EC50 = 0.96 mug/kg in the AA-induced writhing test and with better in vivo stability than the parent phenol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00387-x

文献信息

• VANILLOID ANALOGUES CONTAINING RESINIFERATOXIN PHARMACOPHORES AS POTENT VANILLOID RECEPTOR AGONISTS AND ANALGESICS, COMPOSITIONS AND USES THEREOF
  申请人：PACIFIC CORPORATION

  公开号：EP1154989B1

  公开（公告）日：2005-12-14
• US6476076B1
  申请人：——

  公开号：US6476076B1

  公开（公告）日：2002-11-05