(2-甲基-1-戊基-1H-吲哚-3-基)-1-萘基甲酮 | 155471-10-6

• 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
• 中文名称: (2-甲基-1-戊基-1H-吲哚-3-基)-1-萘基甲酮
• 英文名称: 1-pentyl-2-methyl-3-(1-naphthoyl)indole
• 英文别名: (2-methyl-1-pentyl-1H-indol-3-yl)-1-naphthalenylmethanone；(2-methyl-1-pentylindol-3-yl)-naphthalen-1-ylmethanone
• CAS: 155471-10-6
• 化学式: C₂₅H₂₅NO
• 分子量: 355.48
• InChiKey: IBBNKINXTRKICJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-甲基-1-戊基-1H-吲哚-3-基)-1-萘基甲酮 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 以42%的产率得到2-methyl-3-(1-naphthalenylmethyl)-1-pentyl-1H-Indole
  参考文献：
  名称：

  3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor

  摘要：

  A series of 1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (9 11) and 2-methyl-1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (12-14) have been synthesized to investigate the hypothesis that cannabimimetic 3-(1-naphthoyl)indoles interact with the CB I receptor by hydrogen bonding to the carbonyl group. Indoles 9-11 have significant (K-i 17-23 nM) receptor affinity, somewhat less than that of the corresponding naphthoylindoles (5, 15, 16). 2-Methyl-1-indoles 12-14 have little affinity for the CB1 receptor, in contrast to 2-methyl-3-(1-naphthoyl)indoles 17-19, which have affinities comparable to those of 5, 15, 16. A cannabimimetic indene hydrocarbon (26) was synthesized and found to have K-i = 26 +/- 4 nM. Molecular modeling and receptor docking studies of naphthoylindole 16, its 2-methyl congener (19) and indolyl-1-naphthylmethanes 11 and 14, combined with the receptor affinities of these cannabimimetic indoles, strongly suggest that these cannabinoid receptor ligands bind primarily by aromatic stacking interactions in the transmembrane helix 3-4-5-6 region of the CB1 receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00451-0

文献信息

• Methods and compositions for treating mucusal tissue disorders
  申请人：The University of North Carolina at Chapel Hill

  公开号：US10406200B2

  公开（公告）日：2019-09-10

  The present invention provides compositions and formulations comprising glutathione with or without thiocyanate and methods of use thereof to treat diseases and disorders in mucosal/epithelial tissue.

  本发明提供了包含谷胱甘肽（含或不含硫氰酸盐）的组合物和制剂及其用于治疗粘膜/上皮组织疾病和失调的方法。
• Methods and compositions for treating mucosal tissue disorders
  申请人：The University of North Carolina at Chapel Hill

  公开号：US11058743B2

  公开（公告）日：2021-07-13

  The present invention provides compositions and formulations comprising glutathione with or without thiocyanate and methods of use thereof to treat diseases and disorders in mucosal/epithelial tissue.

  本发明提供了包含谷胱甘肽（含或不含硫氰酸盐）的组合物和制剂及其用于治疗粘膜/上皮组织疾病和失调的方法。
• COMPOSITIONS COMPRISING A CANNABINOID RECEPTOR BINDING LIGAND
  申请人：Novaliq GmbH

  公开号：EP3518921B1

  公开（公告）日：2021-08-11
• Methods and Compositions for Treating Mucosal Tissue Disorders
  申请人：The University of North Carolina at Chapel Hill

  公开号：US20150010654A1

  公开（公告）日：2015-01-08

  The present invention provides compositions and formulations comprising glutathione with or without thiocyanate and methods of use thereof to treat diseases and disorders in mucosal/epithelial tissue.
• METHODS AND COMPOSITIONS FOR TREATING MUCUSAL TISSUE DISORDERS
  申请人：The University of North Carolina at Chapel Hill

  公开号：US20160228490A1

  公开（公告）日：2016-08-11

  The present invention provides compositions and formulations comprising glutathione with or without thiocyanate and methods of use thereof to treat diseases and disorders in mucosal/epithelial tissue.