5-methoxy-7-benzoyl-6-azaindoline | 727993-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methoxy-7-benzoyl-6-azaindoline
• 英文别名: 5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-7-yl(phenyl)methanone；Methanone,(2,3-dihydro-5-methoxy-1h-pyrrolo[2,3-c]pyridin-7-yl)phenyl-；(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-7-yl)-phenylmethanone
• CAS: 727993-77-3
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: MPRFGGJXMYIHSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-7-benzoyl-6-azaindoline 在 吡啶 、 2,4,6-三异丙基苯磺酰叠氮化物 、 potassium tert-butylate 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 8-Amino-4-methoxy-6-phenyl-1,2-dihydro-8H-5,7,9a-triaza-benzo[cd]azulen-9-one
  参考文献：
  名称：

  New substituted triaza-benzo[cd]azulen-9-ones as promising phosphodiesterase-4 inhibitors

  摘要：

  DOI：

  10.1016/j.bmcl.2004.03.067
• 作为产物：
  描述：

  5-氨基-2-甲氧基吡啶 在 正丁基锂 、 四甲基乙二胺 、 氢溴酸 、 双氧水 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-methoxy-7-benzoyl-6-azaindoline
  参考文献：
  名称：

  Preparation of azaindolines and benzoyl substituted azaindolines: precursors of triazabenzo[cd]azulen-9-one PDE4 inhibitors

  摘要：

  The syntheses of various substituted azaindolines are described. Azaindolines were identified as potential key intermediates towards new PDE4 inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.009

文献信息

• Azabenzodiazepines as pde4 inhibitors
  申请人：Warner-Lambert Company LLC

  公开号：EP1526135A1

  公开（公告）日：2005-04-27

  Compounds of formula (I): characterized in that: R1 represents a group selected from hydrogen atom, methyl, methoxy, hydroxy, amino, dimethylamino, acetamido, pyrrolidin-1-yl, and hydroxymethyl; R2 represent a group selected from phenyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, indolyl, pyrolyl, [1,2,3]-triazolyl, benzo[c]isoxazolyl, thienyl, pyrazolyl, isothiazolyl, imidazolyl, benzofuranyl, pyrazolo[5,1-c][1,2,4]triazyl each of these groups being optionally substituted from 1 to 3 groups, identical or different independently of each other, selected from halogen, trifluoromethyl, (C1-C4)alkyl, (C1-C4)alkoxy, hydroxy, amino, acetamido, tert-butyloxycarbonylamino, cycloalkylcarbonylamino, sulfonamide, nitro, acetylmethoxy, cyclopentyloxy; optionally, their optical isomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and their use as active ingredient in pharmaceutical composition useful for treating diseases involving therapy by inhibition of PDE4.

  式（I）化合物的特征在于：R1代表从氢原子、甲基、甲氧基、羟基、氨基、二甲胺基、乙酰胺基、吡咯烷-1-基和羟甲基中选择的基团；R2代表从苯基、吡啶基、嘧啶基、喹啉基、异喹啉基、吲哚基、吡咯基、[1,2,3]-三唑基、苯并[c]异噁唑基、噻吩基、吡唑基、异噻唑基、咪唑基、苯并呋喃基、吡唑并[5,1-c][1,2,4]三唑基中选择的基团，这些基团中的每一个可以从1到3个独立选择的卤素、三氟甲基、（C1-C4）烷基、（C1-C4）氧基、羟基、氨基、乙酰胺基、叔丁氧羰胺基、环烷基羰胺基、磺酰胺基、硝基、乙酰甲氧基、环戊氧基进行选择的取代基；可选地，它们的光学异构体，以及它们与药学上可接受的酸或碱形成的加合物，以及它们作为药用组合物中的活性成分的用途，用于治疗涉及通过抑制PDE4进行治疗的疾病。
• [EN] AZABENZODIAZEPINES AS PHOSPHODIESTERASE-4 INHIBITORS<br/>[FR] AZABENZODIAZEPINES A TITRE D'INHIBITEURS DE LA PHOSPHODIESTERASE-4
  申请人：WARNER LAMBERT CO

  公开号：WO2005040168A1

  公开（公告）日：2005-05-06

  Compounds of formula (I): characterized in that: • Rl represents a group selected from hydrogen atom, methyl, methoxy, hydroxy, amino, dimethylamino, acetamido, pyrrolidin-l-yl, and hydroxymethyl; • R2 represent a group selected from phenyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, indolyl, pyrolyl, [1,2,3]-triazolyl, benzo[c]isoxazolyl, thienyl, pyrazolyl, isothiazolyl, imidazolyl, benzofuranyl, pyrazolo[5,1-c][1,2,4]triazyl each of these groups being optionally substituted from 1 to 3 groups, identical or different independently of each other, selected from halogen, trifluoromethyl, (C1-C4)alkyl, (CI-C4)alkoxy, hydroxy, amino, acetamido, tert-butyloxycarbonylamino, cycloalkylcarbonylamino, sulfonamide, nitro, acetylmethoxy, cyclopentyloxy; optionally, their optical isomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and their use as active ingredient in pharmaceutical composition useful for treating diseases involving therapy by inhibition of PDE4.
• Preparation of azaindolines and benzoyl substituted azaindolines: precursors of triazabenzo[cd]azulen-9-one PDE4 inhibitors
  作者：Matthew Badland、Ingrid Devillers、Corinne Durand、Véronique Fasquelle、Bernard Gaudillière、Henry Jacobelli、Ajith C. Manage、Isabelle Pevet、Jocelyne Puaud、Anthony J. Shorter、Roger Wrigglesworth

  DOI：10.1016/j.tetlet.2011.08.009

  日期：2011.10

  The syntheses of various substituted azaindolines are described. Azaindolines were identified as potential key intermediates towards new PDE4 inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.
• New substituted triaza-benzo[cd]azulen-9-ones as promising phosphodiesterase-4 inhibitors
  作者：Ingrid Devillers、Isabelle Pevet、Henry Jacobelli、Corinne Durand、Véronique Fasquelle、Jocelyne Puaud、Bernard Gaudillière、Moulay Idrissi、François Moreau、Roger Wrigglesworth

  DOI：10.1016/j.bmcl.2004.03.067

  日期：2004.6