4-(2-azidoethoxy)-3-methoxybenzylisothiocyanate | 289903-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2-azidoethoxy)-3-methoxybenzylisothiocyanate
• 英文别名: 1-(2-Azidoethoxy)-4-isothiocyanatomethyl-2-methoxy Benzene；1-(2-Azidoethoxy)-4-(isothiocyanatomethyl)-2-methoxybenzene
• CAS: 289903-56-6
• 化学式: C₁₁H₁₂N₄O₂S
• 分子量: 264.308
• InChiKey: ZBBFXDLIMQBAHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2-azidoethoxy)-3-methoxybenzylisothiocyanate 在 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 39.0h， 生成 2,2-Dimethyl Propionic Acid 2-{3-[4-(2-Aminoethoxy)-3-methoxybenzyl]thioureido Methyl}-3-(3,4-dimethylphenyl)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 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 4-(2-azidoethoxy)-3-methoxybenzylisothiocyanate
  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花椒毒素药效团的新香草酸类似物，包括这种类似物的药物组合物，以及它们作为香草受体激动剂和强效止痛药的用途。本发明提供了一种用于治疗急性、慢性、炎症性或神经病性疼痛或治疗膀胱过敏的药物组合物。
• Simplified resiniferatoxin analogues as vanilloid receptor agonist showing excellent analgesic activity and the pharmaceutical compositions containing the same
  申请人：——

  公开号：US20040063786A1

  公开（公告）日：2004-04-01

  The present invention is related to new vanilloid analogues containing resiniferatoxin pharmacophores, pharmaceutical compositions that have such analogues, and their uses as vanilloid receptor agonists and potent analgesics. The present invention provides a pharmaceutical composition for preventing, alleviating or treating pain, acute pain, chronic pain, neuropathic pain, post-operative pain, migraine, arthralgia, neutopathies, nerve injury, diabetic neuropathy, neurodegeneration, neurotic skin disorder, stroke, urinary bladder hypersensitiveness, irritable bowel syndrome, a respiratory disorder such as asthma or chronic obstructive pulmonary disease, irritation of skin, eye or mucous membrane, fervescence, stomach-duodenal ulcer, inflammatory bowel disease, inflammatory disease or urgent urinary incontinence.

  本发明涉及含有树脂毒素药效团的新型植物辣椒素类似物、具有此类类似物的药物组合物以及它们作为植物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预防、缓解或治疗疼痛、急性疼痛、慢性疼痛、神经病理性疼痛、术后疼痛、偏头痛、关节痛、神经病、神经损伤、糖尿病神经病变、神经退行性疾病、神经性皮肤病、中风、膀胱过敏、肠易激综合征、呼吸系统疾病，如哮喘或慢性阻塞性肺病、皮肤、眼睛或粘膜刺激、发热、胃十二指肠溃疡、炎症性肠病、炎症性疾病或紧急性尿失禁的药物组合物。
• 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
• US6872748B2
  申请人：——

  公开号：US6872748B2

  公开（公告）日：2005-03-29