2-methyl-3-(4-toluoyl)indole | 26211-87-0

• 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: 2-methyl-3-(4-toluoyl)indole
• 英文别名: 3-(4-methylbenzoyl)-2-methyl-1H-indole；(2-methyl-1H-indol-3-yl)(p-tolyl)methanone；(2-methyl-indol-3-yl)-p-tolyl-methanone；(2-Methyl-indol-3-yl)-p-tolyl-keton；(2-Methyl-1 H-indol-3-yl)(4-methylphenyl)methanone；(2-methyl-1H-indole-3-yl)(4-methylphenyl)methanone；(2-methyl-1H-indol-3-yl)-(4-methylphenyl)methanone
• CAS: 26211-87-0
• 化学式: C₁₇H₁₅NO
• mdl: MFCD12653741
• 分子量: 249.312
• InChiKey: IABBMFHGQKDLLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.117
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(4-toluoyl)indole 在 盐酸 、 甲醇 、 dimethyl sulfide borane 、 氧气 、 臭氧 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 2-aminophenyl 4-tolylmethyl ketone
  参考文献：
  名称：

  Clark, Brian J.; Grayshan, Roger, Journal of Chemical Research, Miniprint, 1981, # 10, p. 3786 - 3795

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基吲哚 生成 2-methyl-3-(4-toluoyl)indole
  参考文献：
  名称：

  EP1837329

  摘要：

  公开号：

文献信息

• Novel Heteroaryl Derivative
  申请人：Takahashi Yoko

  公开号：US20080167306A1

  公开（公告）日：2008-07-10

  A compound of the following formula (1), or its prodrug or pharmaceutically acceptable salt thereof, being useful as a diabetic medicine or preventive, or blood sugar regulator, or therapeutic agent for hyperlipemia, etc. wherein the ring Z is an optionally substituted heteroaryl, W 4 is a single bond, lower alkylene, etc., Ar 2 is an optionally substituted aryl, etc., W 3 is a single bond, lower alkylene, etc., Ar 1 is an optionally substituted arylene, etc., each of W 1 and W 2 is an optionally substituted lower alkylene, etc., and R 1 is carboxyl, an alkoxycarbonyl.

  下列式子（1）的化合物，或其前药或其药学上可接受的盐，被用作糖尿病药物或预防药物，或血糖调节剂，或高脂血症等治疗剂。其中，环Z是可选取代的杂芳基，W4是单键，低碳链等，Ar2是可选取代的芳基等，W3是单键，低碳链等，Ar1是可选取代的芳烃基等，W1和W2是可选取代的低碳链等，R1是羧基，烷氧羰基等。
• HETEROARYL DERIVATIVES
  申请人：TAKAHASHI Yoko

  公开号：US20100286144A1

  公开（公告）日：2010-11-11

  A compound of the following formula (1), or its prodrug or pharmaceutically acceptable salt thereof, being useful as a diabetic medicine or preventive, or blood sugar regulator, or therapeutic agent for hyperlipemia, etc. wherein the ring Z is an optionally substituted heteroaryl, W 4 is a single bond, lower alkylene, etc., Ar 2 is an optionally substituted aryl, etc., W 3 is a single bond, lower alkylene, etc., Ar 1 is an optionally substituted arylene, etc., each of W 1 and W 2 is an optionally substituted lower alkylene, etc., and R 1 is carboxyl, an alkoxycarbonyl.

  以下式子（1）的化合物，或其前药或药学上可接受的盐，可用作糖尿病药物、预防药物、血糖调节剂或高脂血症等治疗剂。 其中，环Z是可选取的取代杂环基，W4是单键，低碳烷基等，Ar2是可选取的取代芳基等，W3是单键，低碳烷基等，Ar1是可选取的取代芳烃基等，W1和W2各自是可选取的取代低碳烷基等，R1是羧基，烷氧羰基等。
• NOVEL HETEROARYL DERIVATIVE
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1837329A1

  公开（公告）日：2007-09-26

  A compound of the following formula (1), or its prodrug or pharmaceutically acceptable salt thereof, being useful as a diabetic medicine or preventive, or blood sugar regulator, or therapeutic agent for hyperlipemia, etc. wherein the ring Z is an optionally substituted heteroaryl, W4 is a single bond, lower alkylene, etc., Ar2 is an optionally substituted aryl, etc., W3 is a single bond, lower alkylene, etc., Ar1 is an optionally substituted arylene, etc., each of W1 and W2 is an optionally substituted lower alkylene, etc., and R1 is carboxyl, an alkoxycarbonyl.

  下式(1)化合物或其原药或药学上可接受的盐，可用作糖尿病药物或预防药物，或血糖调节剂，或高脂血症治疗剂等。 其中，环 Z 是任选取代的杂芳基，W4 是单键、低级亚烷基等，Ar2 是任选取代的芳基等，W3 是单键、低级亚烷基等，Ar1 是任选取代的芳基等，W1 和 W2 各自是任选取代的低级亚烷基等，R1 是羧基、烷氧羰基。
• WO2006/75638
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.

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