N-(4-cyanomethylphenyl)methanesulfonamide | 33893-37-7

• 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-(4-cyanomethylphenyl)methanesulfonamide
• 英文别名: 4-((methylsulfonyl)amino)benzyl cyanide；4-Methanesulfonamidobenzylcyanide；4-methanesulfonylaminobenzyl cyanide；N-Methansulfonamido-benzylcyanid；n-[4-(Cyanomethyl)phenyl]methanesulfonamide
• CAS: 33893-37-7
• 化学式: C₉H₁₀N₂O₂S
• 分子量: 210.257
• InChiKey: IABBFZUIRINZBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-cyanomethylphenyl)methanesulfonamide 在 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 生成 2-[4-(methylsulfonylamino)phenyl]ethylamine hydrochloride
  参考文献：
  名称：

  Analysis of structure–activity relationships with the N-(3-acyloxy-2-benzylpropyl)-N′-[4-(methylsulfonylamino)benzyl]thiourea template for vanilloid receptor 1 antagonism

  摘要：

  In a continuing effort to elucidate the structure-activity relationships of the lead antagonist N-[2-(3,4-dimethylbenzyl)-3-pivaloyloxypropyl]-N'-[4-(methylsulfonylamino)benzyl]thiourea (1), the distances between the proposed four pharmacophores in 1 have been varied by insertion or deletion of one carbon to optimize their fit to the receptor. In addition, the acyloxy group of the C region was replaced with amide and N-hydroxy amide to identify the pharmacophoric importance of the ester group in the C2 region. The results indicated that the pharmacophoric arrangement of 1 was optimal for receptor binding affinity and antagonism, and the ester of the C2 region was significant for receptor binding. Among the derivatives, compound 19 showed distinct behavior with a 2-fold improvement in antagonism but a 13-fold reduction in binding affinity compared to 1. The partial separation of pharmacophoric requirements of these two assays has been noted before and compound 19 is thus selective for the calcium entry-linked receptor population. The conformational analysis of 1 generated three distinct conformers having different types of hydrophobic interactions, which will be utilized for exploring the active conformation of the VR1 ligand. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.040
• 作为产物：
  描述：

  对氨基苯乙腈 、 甲基磺酰氯 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到N-(4-cyanomethylphenyl)methanesulfonamide
  参考文献：
  名称：

  Novel thiourea derivatives and the pharmaceutical compositions containing the same

  摘要：

  本发明涉及一种新型硫脲衍生物，作为辣椒素受体（VR）的调节剂，以及含有该衍生物的药物组合物。作为与辣椒素受体活性相关的疾病，可以列举急性疼痛、慢性疼痛、神经痛、术后疼痛、偏头痛、关节痛、神经病变、神经损伤、糖尿病性神经病变、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病等呼吸道疾病、皮肤、眼睛或黏膜刺激、发热、胃十二指肠溃疡、炎症性肠病和炎症性疾病。本发明提供了一种用于预防或治疗这些疾病的药物组合物。

  公开号：

  US20030153596A1

文献信息

• Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: potent agonists for 5-HT1D receptors
  作者：Leslie J. Street、Raymond Baker、Jose L. Castro、Mark S. Chambers、Alexander R. Guiblin、Sarah C. Hobbs、Victor G. Matassa、Austin J. Reeve、Margaret S. Beer

  DOI：10.1021/jm00063a003

  日期：1993.5

  The selectivity of these compounds for 5-HT1D receptors over other serotonergic receptors is discussed. Sulfonamide 20t shows > or = 1000-fold selectivity for 5-HT1D over 5-HT2, 5-HT1C, and 5-HT3 receptors and 10-fold selectivity with respect to 5-HT1A receptors. The functional activity of this series of compounds is studied and demonstrates high 5-HT1D receptor potency and efficacy comparable to that

  描述了一系列新的5-（恶二唑基）色胺的合成和5-HT1D受体活性。研究了恶二唑3-取代基的修饰，连接链的长度（n）和胺取代基，并揭示了5-HT1D受体域中的大结合口袋。容纳恶二唑取代基如苄基而不会损失激动剂的效力或功效。在苯基或苄基间隔基团上引入极性官能团会导致亲和力和功能效能提高10倍。当杂环与吲哚偶联时，观察到最佳的5-HT1D活性，苄基磺酰胺20t和20u代表了一些已知的最有效的5-HT1D激动剂。杂环中的S取代O导致效能进一步提高。删除恶二唑N-2不会降低活性，建议在此位置仅需要一个H键受体。讨论了这些化合物对5-HT1D受体相对于其他血清素能受体的选择性。磺酰胺20t对5-HT1D的选择性比5-HT2、5-HT1C和5-HT3受体高> 1000倍，对5-HT1A受体的选择性高10倍。研究了该系列化合物的功能活性，并证明了与5-HT相当的5-HT1D受体效能和功效。
• [EN] NOVEL THIOUREA DERIVATIVES AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME<br/>[FR] NOUVEAUX DERIVES DE THIOUREA ET COMPOSITIONS PHARMACEUTIQUES RENFERMANT CEUX-CI
  申请人：PACIFIC CORP

  公开号：WO2002016318A1

  公开（公告）日：2002-02-28

  The present invention relates to novel thiourea derivatives as a modulator for vanilloid receptor (VR) and the pharmaceutical compositions containing the same. As diseases associated with the activity of vanilloid receptor, 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 and inflammatory diseases can be enumerated. The present invention provides a pharmaceutical composition for prevention or treatment of these diseases.

  本发明涉及一种新型硫脲衍生物，作为vanilloid受体（VR）的调节剂以及含有该化合物的制药组合物。作为与vanilloid受体活性相关的疾病，可以列举急性疼痛、慢性疼痛、神经病性疼痛、术后疼痛、偏头痛、关节痛、神经病变、神经损伤、糖尿病神经病变、神经退行性疾病、神经性皮肤疾病、中风、膀胱过敏、肠易激综合症、哮喘或慢性阻塞性肺疾病、皮肤、眼或粘膜刺激、发热、胃十二指肠溃疡、炎症性肠病和炎症性疾病等。本发明提供了用于预防或治疗这些疾病的制药组合物。
• CCR5 modulators
  申请人：Agouron Pharmaceuticals, Inc.

  公开号：US07217714B1

  公开（公告）日：2007-05-15

  Compounds of Formula 1 [Region α]−[Region β]−[Region γ]−[Region δ]   (I) which are useful as modulators of chemokine activity. The invention also provides pharmaceutical formulations and methods of treatment using these compounds.

  该发明提供了公式1 [区域α] - [区域β] - [区域γ] - [区域δ] 的化合物(I)，这些化合物可用作趋化因子活性的调节剂。此外，该发明还提供了制药配方和使用这些化合物的治疗方法。
• Bora, Rajesh O.; Farooqui, Mazahar, Journal of the Indian Chemical Society, 2008, vol. 85, # 5, p. 569 - 573
  作者：Bora, Rajesh O.、Farooqui, Mazahar

  DOI：——

  日期：——
• Analysis of structure–activity relationships for the ‘A-region’ of N-(4-t-butylbenzyl)-N′-[4-(methylsulfonylamino)benzyl]thiourea analogues as TRPV1 antagonists
  作者：Jeewoo Lee、Sang-Uk Kang、Min-Jung Kil、Myoungyoup Shin、Ju-Ok Lim、Hyun-Kyung Choi、Mi-Kyoung Jin、Su Yeon Kim、Sung-Eun Kim、Yong-Sil Lee、Kyung-Hoon Min、Young-Ho Kim、Hee-Jin Ha、Richard Tran、Jacqueline D. Welter、Yun Wang、Tamas Szabo、Larry V. Pearce、Daniel J. Lundberg、Attila Toth、Vladimir A. Pavlyukovets、Matthew A. Morgan、Peter M. Blumberg

  DOI：10.1016/j.bmcl.2005.06.009

  日期：2005.9

  The structure-activity relationships for the 'A-region' of N-(4-t-butylbenzyl)-N '-[4-(methylsulfonylamino)benzyl]thio-urea analogues have been investigated as TRPV1 receptor antagonists. The 2-halogen analogues showed enhanced antagonism compared to the prototype antagonist. (c) 2005 Elsevier Ltd. All rights reserved.