1H-pyrrolo[3,2-b]quinoline-3-carbaldehyde | 25957-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1H-pyrrolo[3,2-b]quinoline-3-carbaldehyde
• 英文别名: 1H-pyrrolo[3,2-b]quinoline-3-carbaldehyde；1H-Pyrrolo-<3,2-b>-chinolin-3-carbaldehyd；3-Formyl-1,4-diazabenz--inden
• CAS: 25957-74-8
• 化学式: C₁₂H₈N₂O
• 分子量: 196.208
• InChiKey: GMUZLGVIQYJZRW-UHFFFAOYSA-N

物化性质

• 熔点：
  282-283 °C(Solv: ethanol (64-17-5))
• 沸点：
  458.8±25.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-pyrrolo[3,2-b]quinoline-3-carbaldehyde 生成 3-bromo-1,3-dihydropyrrolo[3,2-b]quinolin-2-one
  参考文献：
  名称：

  PARRICK, JOHN;YAHYA, ARBAEYAH;IJAZ, ABDUL S.;YIZUN, JIN, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N1, C. 2009-2015

  摘要：

  DOI：
• 作为产物：
  描述：

  邻硝基苯甲醇 在 吡啶 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 palladium 10% on activated carbon 、 氢气 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 90.0 ℃ 、413.7 kPa 条件下， 反应 67.0h， 生成 1H-pyrrolo[3,2-b]quinoline-3-carbaldehyde
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of novel polycyclic heteroarene ethers as PDE10A inhibitors: Part I

  摘要：

  We report analogue-based rational design and synthesis of two novel series of polycyclic heteroarenes, pyrrolo[3,2-b]quinolines and pyrido[2,3-b]indoles, tethered to a biaryl system by a methyl-, ethyl-or propyl ether as PDE10A inhibitors. A number of analogues were prepared with variable chain length and evaluated for their ability to block PDE10A enzyme using a radiometric assay. Detailed SAR analyses revealed that compounds with an ethyl ether linker are superior in potency compared to compounds with methyl or propyl ether linkers. These compounds, in general, showed poor metabolic stability in rat and human liver microsomes. The metabolic profile of one of the potent compounds was studied in detail to identify metabolic liabilities of these compounds. Structural modifications were carried out that resulted in improved metabolic stability without significant loss of potency. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.054

文献信息

• Diazaindenes (azaindoles). Part III. Reactions of Vilsmeier reagents leading to 3-formyl-1,6-diazaindene and -1,4-diazabenz[f]indene
  作者：B. A. J. Clark、J. Parrick、P. J. West、A. H. Kelly

  DOI：10.1039/j39700000498

  日期：——

  The action of the two Vilsmeier reagents from dimethylformamide and phosphoryl chloride or thionyl chloride on 2-amino-3-picoline, 3-amino-4-picoline, and 4-amino-3-picoline is reported. The first reagent with 3-amino-4-picoline gave 3-formyl-1,6-diazaindene (pyrrolo[2,3-c]pyridine-3-carbaldehyde) and NN-dimethyl-N′-(4-methyl-3-pyridyl)formamidine, and with 3-amino-2-methylquinoline yielded 3-formyl-1

  报道了来自二甲基甲酰胺和磷酰氯或亚硫酰氯的两种Vilsmeier试剂对2-氨基-3-甲基吡啶，3-氨基-4-甲基吡啶和4-氨基-3-甲基吡啶的作用。与3-氨基-4-甲基吡啶的第一试剂，得到3-甲酰基-1,6- diazaindene（吡咯并[2,3- c ^ ]吡啶-3-甲醛）和NN二甲基Ñ ' - （4-甲基-3- -吡啶基）甲idine，并与3-氨基-2-甲基喹啉生成3-甲酰基-1,4-二氮杂苯并[ f ]-茚（吡咯并[3,2 - b ]喹啉-3-甲醛）。研究了醛的一些改性。3-（NN二甲基氨基甲基）-1,6-二diazaindene制备。
• PARRICK, JOHN;YAHYA, ARBAEYAH;IJAZ, ABDUL S.;YIZUN, JIN, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N1, C. 2009-2015
  作者：PARRICK, JOHN、YAHYA, ARBAEYAH、IJAZ, ABDUL S.、YIZUN, JIN

  DOI：——

  日期：——
• Design, synthesis and pharmacological evaluation of novel polycyclic heteroarene ethers as PDE10A inhibitors: Part I
  作者：Sanjib Das、Rajendra L. Harde、Dnyaneshwar E. Shelke、Neelima Khairatkar-Joshi、Malini Bajpai、Ratika S. Sapalya、Harshada V. Surve、Girish S. Gudi、Rambabu Pattem、Dayanidhi B. Behera、Satyawan B. Jadhav、Abraham Thomas

  DOI：10.1016/j.bmcl.2014.03.054

  日期：2014.5

  We report analogue-based rational design and synthesis of two novel series of polycyclic heteroarenes, pyrrolo[3,2-b]quinolines and pyrido[2,3-b]indoles, tethered to a biaryl system by a methyl-, ethyl-or propyl ether as PDE10A inhibitors. A number of analogues were prepared with variable chain length and evaluated for their ability to block PDE10A enzyme using a radiometric assay. Detailed SAR analyses revealed that compounds with an ethyl ether linker are superior in potency compared to compounds with methyl or propyl ether linkers. These compounds, in general, showed poor metabolic stability in rat and human liver microsomes. The metabolic profile of one of the potent compounds was studied in detail to identify metabolic liabilities of these compounds. Structural modifications were carried out that resulted in improved metabolic stability without significant loss of potency. (C) 2014 Elsevier Ltd. All rights reserved.