1-pentyl-1H-indol-3-yl-(4-methoxy-1-naphthyl)methane | 619294-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-pentyl-1H-indol-3-yl-(4-methoxy-1-naphthyl)methane
• 英文别名: 1H-Indole, 3-((4-methoxy-1-naphthalenyl)methyl)-1-pentyl-；3-[(4-methoxynaphthalen-1-yl)methyl]-1-pentylindole
• CAS: 619294-39-2
• 化学式: C₂₅H₂₇NO
• 分子量: 357.495
• InChiKey: OTYBPWBZUDBUQS-UHFFFAOYSA-N

物化性质

• 沸点：
  536.6±30.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-戊基-3-(4-甲氧基萘甲酰基)吲哚 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 以68%的产率得到1-pentyl-1H-indol-3-yl-(4-methoxy-1-naphthyl)methane
  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
• [EN] PHARMACEUTICAL COMPOSITIONS AND METHODS FOR TREATING PARKINSON'S DISEASE<br/>[FR] COMPOSITIONS PHARMACEUTIQUES ET MÉTHODES DE TRAITEMENT DE LA MALADIE DE PARKINSON
  申请人：PIKE THERAPEUTICS INC

  公开号：WO2022038475A1

  公开（公告）日：2022-02-24

  The current application relates to a topical pharmaceutical composition comprising at least one active agent selected from CBD and THC, solvent, surfactant, optional permeation enhancer, and optional adhesive/polymer. The topical composition is used for treating, preventing, or slowing the onset or progression of Parkinson's disease and/or related symptoms.
• [EN] TRANSDERMAL PHARMACEUTICAL FORMULATIONS FOR THE TREATMENT OF MULTIPLE SCLEROSIS<br/>[FR] FORMULATIONS PHARMACEUTIQUES TRANSDERMIQUES POUR LE TRAITEMENT DE LA SCLÉROSE EN PLAQUES
  申请人：PIKE THERAPEUTICS INC

  公开号：WO2022003623A1

  公开（公告）日：2022-01-06

  The present disclosure relates to the to the transdermal administration of THC and/or CBD and derivatives of these compounds, for the treatment and/or prevention and/or control of multiple sclerosis, multiple sclerosis-related muscle spasms, and pain and/or spasticity in multiple sclerosis.
• 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.