甲酮,[1-(4-溴丁基)-2-甲基-1H-吲哚-3-基](4-甲氧苯基)- | 103608-56-6

• 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: 甲酮,[1-(4-溴丁基)-2-甲基-1H-吲哚-3-基](4-甲氧苯基)-
• 英文名称: <1-(4-bromobutyl)-2-methyl-1H-indol-3-yl>(4-methoxyphenyl)methanone
• 英文别名: 1-(4-bromobutyl)-2-methyl-3-(4-methoxybenzoyl)-1H-indole；[1-(4-Bromobutyl)-2-methylindol-3-yl]-(4-methoxyphenyl)methanone
• CAS: 103608-56-6
• 化学式: C₂₁H₂₂BrNO₂
• 分子量: 400.315
• InChiKey: BMYZACXFSQRETI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  杂氮环丁烷 、 甲酮,[1-(4-溴丁基)-2-甲基-1H-吲哚-3-基](4-甲氧苯基)- 生成 [1-[3-(3-Chloropropylamino)propyl]-2-methylindol-3-yl]-(4-methoxyphenyl)methanone;hydrochloride
  参考文献：
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  摘要：

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• 作为产物：
  描述：

  1,4-二溴丁烷 生成 甲酮,[1-(4-溴丁基)-2-甲基-1H-吲哚-3-基](4-甲氧苯基)-
  参考文献：
  名称：

  摘要：

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文献信息

• 3-arylcarbonyl- and 3-cycloalkylcarbonyl-1-aminoalkyl-1H-indoles,
  申请人：Sterling Drug Inc.

  公开号：US04581354A1

  公开（公告）日：1986-04-08

  3-Arylcarbonyl- and 3-cycloalkylcarbonyl-1-aminoalkyl-1H-indoles, useful as analgesic, anti-rheumatic and anti-inflammatory agents, are prepared by reacting a 3-arylcarbonyl- or 3-cycloalkylcarbonylindole with an aminoalkyl halide in the presence of an acid-acceptor; by reacting a 1-aminoalkyl-1H-indole with an arylcarboxylic acid halide or a cycloalkanecarboxylic acid halide in the presence of a Lewis acid; or by reacting a 3-arylcarbonyl- or 3-cycloalkanecarbonyl-1-tosyloxyalky- or haloalkyl-1H-indole with an amine.

  3-芳基羰基和3-环烷基羰基-1-氨基烷基-1H-吲哚，作为镇痛、抗风湿和抗炎药物，通过将3-芳基羰基或3-环烷基羰基吲哚与氨基卤代烷在酸受体存在下反应制备；通过将1-氨基烷基-1H-吲哚与芳基羧酸酰卤或环烷基羧酸酰卤在Lewis酸存在下反应制备；或通过将3-芳基羰基或3-环烷基羰基-1-对甲苯基氧基烷基或卤代烷基-1H-吲哚与胺反应制备。
• Antinociceptive (aminoalkyl)indoles
  作者：Malcolm R. Bell、Thomas E. D'Ambra、Virendra Kumar、Michael A. Eissenstat、John L. Herrmann、Joseph R. Wetzel、David Rosi、Richard E. Philion、Sol J. Daum

  DOI：10.1021/jm00107a034

  日期：1991.3

  The (aminoalkyl)indole (AAI) derivative pravadoline (1a) inhibited prostaglandin (PG) synthesis in mouse brain microsomes in vitro and ex vivo and exhibited antinociceptive activity in several rodent assays. In vitro structure-activity relationship studies of this new class of PG synthesis inhibitors revealed a correspondence in three respects to those reported for the arylacetic acids: (1) ''alpha-methylation'' caused an increase in PG inhibitory potency, (2) the (R)-alpha-methyl isomer was more active than the S isomer, (3) the hypothesized aroyl group conformation of the 2-methyl derivatives corresponded to the proposed and reported ''active'' conformations of the aroyl and related aromatic acetic acid derivatives. The H-1 NMR chemical shift of the C-4 hydrogen of pravadoline in comparison to the deshielding seen with 50, which lacks a substituent at C-2, suggested that the carbonyl group of pravadoline is located near C-2 but is located near C-4 in 50. Associated with this conformational change of the carbonyl group of 1a is a diminution of PG synthetase inhibitory activity. The results of UV and difference nuclear Overhauser studies of the two compounds were consistent with these conformational assignments. The low eudismic ratios of the alpha-methyl derivatives and the observation that the side chain may be extended by three methylene groups without significant loss of PG inhibitory potency suggests that this class of inhibitors bound less strongly and less selectively to the active site of PG synthetase than do the arylacetic acids. Two AAIs, 1a and 30, were found to be metabolized to the corresponding acetic acid derivatives, both of which inhibited PG synthesis. An exception to the observation that the antinociceptive activity of the AAIs was associated with PG synthetase inhibitory activity was the 1-naphthoyl derivative 67 since neither it nor its acetic acid metabolite 74 inhibited PG synthesis. Yet 67 was antinociceptive in four different rodent assays. This naphthoyl derivative, like opioids, also inhibited electrically stimulated contractions in the mouse vas deferens (MVD) preparation. Unlike opioids, however, the inhibition was not antagonized by naloxone. A subseries of AAIs was identified, of which 67 was prototypic. These compounds lacked PG synthetase inhibitory activity, but their inhibitory potency in MVD preparations correlated roughly with their antinociceptive potency in vivo. Pravadoline was also inhibitory in the MVD. Its antinociceptive activity, therefore, may be a consequence of both its PG synthetase inhibitory potency and another antinociceptive mechanism, the latter associated with its inhibitory potency in the MVD. The evidence is summarized which suggests that this second antinociceptive mechanism is associated with binding to the recently characterized cannabinoid receptor.
• US32761
  申请人：——

  公开号：——

  公开（公告）日：——
• 3-Carbonyl-1-aminoalkyl-1H-indoles useful as analgesics and preparation thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0171037B1

  公开（公告）日：1992-06-17
• BELL, MALCOLM R.
  作者：BELL, MALCOLM R.

  DOI：——

  日期：——