((S)-1-m-Tolyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester | 474774-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ((S)-1-m-Tolyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3S)-1-(3-methylphenyl)pyrrolidin-3-yl]carbamate
• CAS: 474774-40-8
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: OVLGKSIKCLYXKD-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((S)-1-m-Tolyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-(2-Bromo-phenyl)-3-((S)-1-m-tolyl-pyrrolidin-3-yl)-urea
  参考文献：
  名称：

  Discovery of SB-705498: A potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development

  摘要：

  Small molecule antagonists of the vanilloid receptor TRPV1 (also known as VR1) are disclosed. Pyrrolidinyl ureas such as 8 and 15 (SB-705498) emerged as lead compounds following optimisation of the previously described urea SB-452533. Pharmacological studies using electrophysiological and FLIPR-Ca2+-based assays showed that compounds such as 8 and 15 were potent antagonists versus the multiple chemical and physical modes of TRPV1 activation (namely capsaicin, acid and noxious heat). Furthermore, 15 possessed suitable developability properties to enable progression of this compound into in vivo studies and subsequently clinical development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.030
• 作为产物：
  描述：

  3-溴甲基苯 、 (S)-3-叔丁氧羰基氨基吡咯烷 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 ((S)-1-m-Tolyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of SB-705498: A potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development

  摘要：

  Small molecule antagonists of the vanilloid receptor TRPV1 (also known as VR1) are disclosed. Pyrrolidinyl ureas such as 8 and 15 (SB-705498) emerged as lead compounds following optimisation of the previously described urea SB-452533. Pharmacological studies using electrophysiological and FLIPR-Ca2+-based assays showed that compounds such as 8 and 15 were potent antagonists versus the multiple chemical and physical modes of TRPV1 activation (namely capsaicin, acid and noxious heat). Furthermore, 15 possessed suitable developability properties to enable progression of this compound into in vivo studies and subsequently clinical development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.030

文献信息

• HETEROCYCLIC UREAS, THEIR PREPARATION AND THEIR USE AS VANILLOID RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1392651A1

  公开（公告）日：2004-03-03
• PHENYLPYRROLIDINE COMPOUNDS
  申请人：Falcó José

  公开号：US20120184594A1

  公开（公告）日：2012-07-19

  This invention provides new phenylpyrrolidine compounds, their use for the treatment or prevention of melatoninergic disorders and its compositions.
• [EN] HETEROCYCLIC UREAS, THEIR PREPARATION AND THEIR USE AS VANILLOID RECEPTOR ANTAGONISTS<br/>[FR] UREES HETEROCYCLIQUES, LEUR PREPARATION ET LEUR UTILISATION COMME ANTAGONISTES DU RECEPTEUR VANILLOIDE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2002090326A1

  公开（公告）日：2002-11-14

  The invention relates to compounds of formula (I) having Vanilloid Receptor (VR1) antagonist activity, processes for their preparation, to compositions containing them and to their use in the treatment of various disorders.