N-(4-叔丁基苄基)-N'-[(1R)-1-(4-硝基苯基)乙基]硫脲 | 694529-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-叔丁基苄基)-N'-[(1R)-1-(4-硝基苯基)乙基]硫脲
• 英文名称: N-(4-t-butylbenzyl)-N'-[(1R)-1-(4-nitrophenyl)ethyl]thiourea
• 英文别名: 1-[(4-tert-butylphenyl)methyl]-3-[(1R)-1-(4-nitrophenyl)ethyl]thiourea
• CAS: 694529-13-0
• 化学式: C₂₀H₂₅N₃O₂S
• 分子量: 371.503
• InChiKey: UFCPQKIBKWTZRQ-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-叔丁基苄基)-N'-[(1R)-1-(4-硝基苯基)乙基]硫脲 在 吡啶 、 氢氧化钾 、 氢化铝 、 mercury dichloride 作用下， 以 乙醚 、 水 为溶剂， 反应 0.34h， 生成 SU-388
  参考文献：
  名称：

  [EN] 4-(METHYL SULFONYL AMINO) PHENYL ANALOGUES AS VANILLOID ANTAGONIST SHOWING EXCELLENT ANALGESIC ACTIVITY AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  [FR] ANALOGUES DE 4-(METHYL SULFONYL AMINO)PHENYLE UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR VANILLOIDE AYANT UNE EXCELLENTE ACTIVITE ANALGESIQUE, ET COMPOSITIONS PHARMACEUTIQUE LES COMPRENANT

  摘要：

  本发明涉及一种新型的4-(甲磺胺基)苯基类似物，作为有效的辣椒素受体拮抗剂，以及包含该类似物的药物组合物。这种创新化合物可用于镇痛药，用于预防、缓解或治疗疼痛疾病或包括疼痛的炎症性疾病，如急性疼痛、慢性疼痛、神经痛、术后疼痛、偏头痛、关节痛、神经病、神经损伤、糖尿病性神经病、神经退行性疾病、神经性皮肤疾病、中风、膀胱过敏、肠易激综合征、哮喘或慢性阻塞性肺疾病等呼吸道疾病、皮肤、眼睛或粘膜的刺激、发热、胃十二指肠溃疡、炎症性肠病、炎症性疾病和急性尿失禁。

  公开号：

  WO2005003084A1
• 作为产物：
  描述：

  (R)-1-(4-硝基苯基)-乙胺 、 4-叔-丁基苄基异硫氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-叔丁基苄基)-N'-[(1R)-1-(4-硝基苯基)乙基]硫脲
  参考文献：
  名称：

  Chain-branched 1,3-dibenzylthioureas as vanilloid receptor 1 antagonists

  摘要：

  A series of chain-branched 1,3-dibenzylthiourea derivatives were synthesized, and tested their antagonist activity against vanilloid receptor 1. Chain-branching led to a significant change in the mode of action and the potency. (R)-Methyl or ethyl-branched 1,3-dibenzylthiourea derivatives showed the most potent antagonist activity up to the IC50 value of 0.05 muM which is 10-fold more potent than capsazepine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.066

文献信息

• α-Substituted N-(4-tert-butylbenzyl)-N′-[4-(methylsulfonylamino)benzyl]thiourea analogues as potent and stereospecific TRPV1 antagonists
  作者：Jae-Uk Chung、Su Yeon Kim、Ju-Ok Lim、Hyun-Kyung Choi、Sang-Uk Kang、Hae-Seok Yoon、HyungChul Ryu、Dong Wook Kang、Jeewoo Lee、Bomi Kang、Sun Choi、Attila Toth、Larry V. Pearce、Vladimir A. Pavlyukovets、Daniel J. Lundberg、Peter M. Blumberg

  DOI：10.1016/j.bmc.2007.06.041

  日期：2007.9

  A series of alpha-Substituted N-(4-tert-butylbenzyl)-N'-[4-(methylsulfonylamino)benzyl]thiourea analogues have been investigated as TRPV1 receptor antagonists. alpha-Methyl substituted analogues showed potent and stereospecific antagonism to the action of capsaicin on rat TRPV1 heterologously expressed in Chinese hamster ovary cells. In particular, compounds 14 and 18, which possess the R-configuration, exhibited excellent potencies (respectively, K-i = 41 and 39.2 nM and K-i(ant) = 4.5 and 37 nM). (c) 2007 Published Elsevier Ltd.
• [EN] 4-(METHYL SULFONYL AMINO) PHENYL ANALOGUES AS VANILLOID ANTAGONIST SHOWING EXCELLENT ANALGESIC ACTIVITY AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME<br/>[FR] ANALOGUES DE 4-(METHYL SULFONYL AMINO)PHENYLE UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR VANILLOIDE AYANT UNE EXCELLENTE ACTIVITE ANALGESIQUE, ET COMPOSITIONS PHARMACEUTIQUE LES COMPRENANT
  申请人：DIGITALBIOTECH CO LTD

  公开号：WO2005003084A1

  公开（公告）日：2005-01-13

  The present invention relates to novel 4-(methylsulfonylamino) phenyl analogue as a potent vanilloid receptor antagonist and the pharmaceutical compositions comprising the same. The inventive compound can be useful for analgesics to prevent, alleviate or treat pain diseases or inflammatory disease comprising pain, acute pain, chronic pain, neuropathic pain, post-operative pain, migraine, arthralgia, neuropathies, 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 and urgent urinary incontinence.

  本发明涉及一种新型的4-(甲磺胺基)苯基类似物，作为有效的辣椒素受体拮抗剂，以及包含该类似物的药物组合物。这种创新化合物可用于镇痛药，用于预防、缓解或治疗疼痛疾病或包括疼痛的炎症性疾病，如急性疼痛、慢性疼痛、神经痛、术后疼痛、偏头痛、关节痛、神经病、神经损伤、糖尿病性神经病、神经退行性疾病、神经性皮肤疾病、中风、膀胱过敏、肠易激综合征、哮喘或慢性阻塞性肺疾病等呼吸道疾病、皮肤、眼睛或粘膜的刺激、发热、胃十二指肠溃疡、炎症性肠病、炎症性疾病和急性尿失禁。
• Chain-branched 1,3-dibenzylthioureas as vanilloid receptor 1 antagonists
  作者：Chong Hyun Ryu、Mi Jung Jang、Jeong Wha Jung、Ju-Hyun Park、Hye Young Choi、Young-ger Suh、Uhtaek Oh、Hyeung-geun Park、Jeewoo Lee、Hyun-Joo Koh、Joo-Hyun Mo、Yung Hyup Joo、Young-Ho Park、Hee-Doo Kim

  DOI：10.1016/j.bmcl.2004.01.066

  日期：2004.4

  A series of chain-branched 1,3-dibenzylthiourea derivatives were synthesized, and tested their antagonist activity against vanilloid receptor 1. Chain-branching led to a significant change in the mode of action and the potency. (R)-Methyl or ethyl-branched 1,3-dibenzylthiourea derivatives showed the most potent antagonist activity up to the IC50 value of 0.05 muM which is 10-fold more potent than capsazepine. (C) 2004 Elsevier Ltd. All rights reserved.