tert-butyl N-[4-(2-azidoethoxy)-3-methoxybenzyl]carbamate | 289903-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl N-[4-(2-azidoethoxy)-3-methoxybenzyl]carbamate
• 英文别名: (4-(2-Azido-ethoxy)-3-methoxy-benzyl]-carbamic Acid t-Butyl Ester；tert-butyl N-[[4-(2-azidoethoxy)-3-methoxyphenyl]methyl]carbamate
• CAS: 289903-50-0
• 化学式: C₁₅H₂₂N₄O₄
• 分子量: 322.364
• InChiKey: RXSIYDVFAKGBCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-(2-azidoethoxy)-3-methoxybenzyl]carbamate 在 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 2,2-Dimethyl Propionic Acid 2-{3-[4-(2-Aminoethoxy)-3-methoxybenzyl]thioureido Methyl}-3-(4-t-butylphenyl)propyl Ester
  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：

  香兰素胺盐酸盐 在 氢氧化钾 、 sodium azide 、 四丁基氢氧化铵 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 tert-butyl N-[4-(2-azidoethoxy)-3-methoxybenzyl]carbamate
  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 resinferatoxin pharmacophores as potent vanilloid receptor agonists and analgesics, compositions and uses thereof
  申请人：Pacific Corporation

  公开号：US06476076B1

  公开（公告）日：2002-11-05

  The present invention is related to new vanilloid analogues containing resiniferatoxin pharmacophores, pharmaceutical compositions comprising such analogues, and their uses as vanilloid receptor agonists and potent analgesics. The present invention provides a pharmaceutical composition for treating acute, chronic, inflammatory or neuropathic pains or for treating bladder hypersensitivity.

  本发明涉及含有树脂菲毒素药效团的新型辣椒素类似物、包括这种类似物的制药组合物以及它们作为辣椒素受体激动剂和强效镇痛剂的用途。本发明提供了一种用于治疗急性、慢性、炎症性或神经病理性疼痛或治疗膀胱过敏的制药组合物。
• The SAR analysis of TRPV1 agonists with the α-methylated B-region
  作者：Yongsung Cho、Myeong Seop Kim、Ho Shin Kim、Jihyae Ann、Jiyoun Lee、Larry V. Pearce、Vladimir A. Pavlyukovets、Matthew A. Morgan、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmcl.2012.06.059

  日期：2012.8

  A series of TRPV1 agonists with amide, reverse amide, and thiourea groups in the B-region and their corresponding alpha-methylated analogues were investigated. Whereas the alpha-methylation of the amide B-region enhanced the binding affinities and potencies as agonists, that of the reverse amide and thiourea led to a reduction in receptor affinity. The analysis indicated that proper hydrogen bonding as well as steric effects in the B-region are critical for receptor binding. (c) 2012 Elsevier Ltd. All rights reserved.
• US6476076B1
  申请人：——

  公开号：US6476076B1

  公开（公告）日：2002-11-05
• 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
  作者：Jeewoo Lee、Jiyoun Lee、Myung-Sim Kang、Kang-Pil Kim、Suk-Jae Chung、Peter M. Blumberg、Jung-Bum Yi、Young Ho Park

  DOI：10.1016/s0968-0896(01)00387-x

  日期：2002.4

  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.