2-methyl-3-(1-naphthalenylmethyl)-1-pentyl-1H-Indole | 619294-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-3-(1-naphthalenylmethyl)-1-pentyl-1H-Indole
• 英文别名: 2-methyl-3-(1-naphthylmethyl)-1-pentyl-1H-indole；1H-Indole, 2-methyl-3-(1-naphthalenylmethyl)-1-pentyl-；2-methyl-3-(naphthalen-1-ylmethyl)-1-pentylindole
• CAS: 619294-41-6
• 化学式: C₂₅H₂₇N
• 分子量: 341.496
• InChiKey: LDTJKFUAZQDSQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  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

• COMPOSITION AND METHODS TO IMPROVE STABILITY, DOSING, PHARMACODYNAMICS AND PRODUCT SHELF LIFE OF ENDOCANNABINOIDS, PHYTOCANNABINOIDS AND SYNTHETIC CANNABINOIDS DELIVERED BY NASAL INHALER
  申请人：Willinsky, Michael

  公开号：EP3247402A1

  公开（公告）日：2017-11-29
• 3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor
  作者：John W Huffman、Ross Mabon、Ming-Jung Wu、Jianzhong Lu、Richard Hart、Dow P Hurst、Patricia H Reggio、Jenny L Wiley、Billy R Martin

  DOI：10.1016/s0968-0896(02)00451-0

  日期：2003.2

  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.