1-hexyl-1H-indole-3-carboxylic acid | 858515-72-7

• 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: 1-hexyl-1H-indole-3-carboxylic acid
• 英文别名: 1-hexylindole-3-carboxylic acid
• CAS: 858515-72-7
• 化学式: C₁₅H₁₉NO₂
• mdl: MFCD11542755
• 分子量: 245.321
• InChiKey: YLDNDXMOWNHKAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hexyl-1H-indole-3-carboxylic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [4-[3-(Aminomethyl)phenyl]piperidin-1-yl]-(1-hexylindol-3-yl)methanone;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Design, synthesis, and biological activity of potent and selective inhibitors of mast cell tryptase

  摘要：

  A new series of novel mast cell tryptase inhibitors is reported, which features the use of an indole structure as the hydrophobic substituent on a m-benzylaminepiperidine template. The best members of this series display good in vitro activity and excellent selectivity against other serine proteases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.002
• 作为产物：
  描述：

  1-Hexyl-1H-indole-3-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-hexyl-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and biological activity of potent and selective inhibitors of mast cell tryptase

  摘要：

  A new series of novel mast cell tryptase inhibitors is reported, which features the use of an indole structure as the hydrophobic substituent on a m-benzylaminepiperidine template. The best members of this series display good in vitro activity and excellent selectivity against other serine proteases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.002

文献信息

• Synthesis and Functional Evaluation of Synthetic Cannabinoid Receptor Agonists Related to ADB-HEXINACA
  作者：Eric Sparkes、Axelle Timmerman、Jack W. Markham、Rochelle Boyd、Rebecca Gordon、Katelyn A. Walker、Richard C. Kevin、David E. Hibbs、Samuel D. Banister、Elizabeth A. Cairns、Christophe Stove、Adam Ametovski

  DOI：10.1021/acschemneuro.3c00818

  日期：——

  pharmacological evaluation of ADB-HEXINACA and a library of 41 closely related analogues. Two in vitro functional assays were employed to assess activity at CB1 and CB2 cannabinoid receptors, measuring Gβγ-coupled agonism through a fluorescence-based membrane potential assay (MPA) and β-arrestin 2 (βarr2) recruitment via a live cell-based nanoluciferase complementation reporter assay. ADB-HEXINACA was a potent

  ADB-HEXINACA 最近被报道为一种合成大麻素受体激动剂 (SCRA)，是最大类别的新型精神活性物质 (NPS) 之一。该化合物标志着正己基尾基进入 SCRA 领域，随着最近新检测到的 SCRA 的出现，这种情况在市场上继续存在。因此，开展了一项积极的表征活动，包括 ADB-HEXINACA 和 41 个密切相关类似物的合成、表征和药理学评估。采用两种体外功能测定来评估 CB 1和 CB 2大麻素受体的活性，通过基于荧光的膜电位测定 (MPA) 测量 G βγ偶联激动作用，并通过活细胞招募 β-arrestin 2 (βarr2)基于纳米荧光素酶互补报告基因测定。 ADB-HEXINACA 是一种强效且有效的 CB 1激动剂（CB 1 MPA pEC 50 = 7.87 ± 0.12 M； E max = 124 ± 5%；βarr2 pEC 50 = 8.27 ± 0.14 M； E
• 10.1021/acschemneuro.3c00850
  作者：Sparkes, Eric、Maloney, Callan J.、Markham, Jack W.、Dane, Chianna、Boyd, Rochelle、Gilchrist, Jayson、Moir, Michael、Gordon, Rebecca、Luo, Jia Lin、Pike, Edward、Walker, Katelyn A.、Kassiou, Michael、McGregor, Iain S.、Kevin, Richard C.、Hibbs, David E.、Jorgensen, William T.、Banister, Samuel D.、Cairns, Elizabeth A.、Ametovski, Adam

  DOI：10.1021/acschemneuro.3c00850

  日期：——

  Synthetic cannabinoid receptor agonists (SCRAs) are a growing class of new psychoactive substances (NPS) commonly derived from an N-alkylated indole, indazole, or 7-azaindole scaffold. Diversification of this core (at the 3-position) with amide-linked pendant amino acid groups and modular N-alkylation (of the indole/indazole/7-azaindole core) ensures that novel SCRAs continue to enter the illicit drug

  合成大麻素受体激动剂 (SCRA) 是一类不断增长的新型精神活性物质 (NPS)，通常源自N-烷基化吲哚、吲唑或 7-氮杂吲哚支架。该核心（在 3 位）具有酰胺连接的氨基酸侧基和模块化N-烷基化（吲哚/吲唑/7-氮杂吲哚核心）的多样化确保了新型 SCRA 继续快速进入非法药物市场。鉴于已检测到大量 SCRA，此类 NPS 的药理学评估已变得越来越普遍。自 2011 年以来，金刚烷衍生的 SCRA 一直出现在整个市场中，因此，系统地合成了这些衍生物并进行了药理学评估。制备氘代和氟化金刚烷衍生物以评估典型的氢生物等排体，以及评估新检测到的 AFUBIATA。
• Design, synthesis, and biological activity of potent and selective inhibitors of mast cell tryptase
  作者：Corey R. Hopkins、Mark Czekaj、Steven S. Kaye、Zhongli Gao、James Pribish、Henry Pauls、Guyan Liang、Keith Sides、Dona Cramer、Jennifer Cairns、Yongyi Luo、Heng-Keang Lim、Roy Vaz、Sam Rebello、Sebastian Maignan、Alain Dupuy、Magali Mathieu、Julian Levell

  DOI：10.1016/j.bmcl.2005.04.002

  日期：2005.6

  A new series of novel mast cell tryptase inhibitors is reported, which features the use of an indole structure as the hydrophobic substituent on a m-benzylaminepiperidine template. The best members of this series display good in vitro activity and excellent selectivity against other serine proteases. (c) 2005 Elsevier Ltd. All rights reserved.