adamantan-1-yl-(6-trifluoromethyl-2,3-dihydro-indol-1-yl)methanone | 1422444-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: adamantan-1-yl-(6-trifluoromethyl-2,3-dihydro-indol-1-yl)methanone
• 英文别名: 1-Adamantyl-[6-(trifluoromethyl)-2,3-dihydroindol-1-yl]methanone；1-adamantyl-[6-(trifluoromethyl)-2,3-dihydroindol-1-yl]methanone
• CAS: 1422444-11-8
• 化学式: C₂₀H₂₂F₃NO
• 分子量: 349.396
• InChiKey: UZCKQJYJNVYGCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  金刚烷酰氯 、 6-三氟甲基吲哚啉 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 adamantan-1-yl-(6-trifluoromethyl-2,3-dihydro-indol-1-yl)methanone
  参考文献：
  名称：

  Highly potent and selective cannabinoid receptor 2 agonists: Initial hit optimization of an adamantyl hit series identified from high-through-put screening

  摘要：

  A series of highly potent & selective adamantane derived CB2 agonists was identified in a high-through-put screen. A SAR was established and physicochemical properties were significantly improved. This was accompanied by potency of the compounds on the Q63R variant and varying beta-arrestin data which will support the insight into their relevance for the in vivo situation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.044

文献信息

• NOVEL ADAMANTYL DERIVATIVES AS CANNABINOID RECEPTOR 2 AGONISTS
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150111886A1

  公开（公告）日：2015-04-23

  The invention relates to a compound of formula (I) wherein A 1 , R 1 and R 2 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

  该发明涉及一种化合物，其化学式为（I），其中A1、R1和R2的定义如描述和索赔中所述。该化合物可以用作药物。
• [EN] NOVEL ADAMANTYL DERIVATIVES AS CANNABINOID RECEPTOR 2 AGONISTS<br/>[FR] NOUVEAUX DÉRIVÉS D'ADAMANTYLE EN TANT QU'AGONISTES DU RÉCEPTEUR 2 DE CANNABINOÏDES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014005968A1

  公开（公告）日：2014-01-09

  The invention relates to a compound of formula (I), wherein i.a. A1is -CH2- or -C(O)-; one of R1 and R2 is hydrogen and the other one is -A2 -C(O)-R3; A2 is NH- or absent; and R3 is (A), (B) or (C) The compounds are preferential agonists of the cannabinoid receptor 2 (CB2) and can be used as medicaments for the treatment of pain, inflammation, ischemia, etc.

  这项发明涉及一种化合物，其化学式为（I），其中i.a. A1为-CH2-或-C(O)-；R1和R2中的一个是氢，另一个是-A2-C(O)-R3；A2为NH-或不存在；R3为（A）、（B）或（C）。这些化合物是大麻素受体2（CB2）的优先激动剂，可用作治疗疼痛、炎症、缺血等的药物。
• US9090615B2
  申请人：——

  公开号：US9090615B2

  公开（公告）日：2015-07-28
• Highly potent and selective cannabinoid receptor 2 agonists: Initial hit optimization of an adamantyl hit series identified from high-through-put screening
  作者：Matthias Nettekoven、Jürgen Fingerle、Uwe Grether、Sabine Grüner、Atsushi Kimbara、Bernd Püllmann、Mark Rogers-Evans、Stephan Röver、Franz Schuler、Tanja Schulz-Gasch、Christoph Ullmer

  DOI：10.1016/j.bmcl.2013.01.044

  日期：2013.3

  A series of highly potent & selective adamantane derived CB2 agonists was identified in a high-through-put screen. A SAR was established and physicochemical properties were significantly improved. This was accompanied by potency of the compounds on the Q63R variant and varying beta-arrestin data which will support the insight into their relevance for the in vivo situation. (C) 2013 Elsevier Ltd. All rights reserved.