1-乙基-3-甲基-4-氯-1H-吡唑并[3,4-b]喹啉 | 100935-86-2

• 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
• 中文名称: 1-乙基-3-甲基-4-氯-1H-吡唑并[3,4-b]喹啉
• 英文名称: 1-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline
• 英文别名: 4-chloro-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]quinoline；4-chloro-1-ethyl-3-methylpyrazolo[3,4-b]quinoline
• CAS: 100935-86-2
• 化学式: C₁₃H₁₂ClN₃
• 分子量: 245.711
• InChiKey: HRYRNEAKFBVNNM-UHFFFAOYSA-N

物化性质

• 沸点：
  411.5±40.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-乙基-3-甲基-4-氯-1H-吡唑并[3,4-b]喹啉 、 4-胺基丙苯酮 在 苯酚 作用下， 以67%的产率得到1-ethyl-3-methyl-N-(4-propionylphenyl)-1H-pyrazolo[3,4-b]quinolin-4-amine
  参考文献：
  名称：

  Discovery and structure–activity relationship of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as a new series of potent apoptosis inducers

  摘要：

  We report the discovery and SAR study of a series of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as potent inducers of apoptosis. N-(3-Acetylphenyl)-2,3-dihydro-1H-cyclopenta[b]quinolin-9-amine (2) was discovered through our cell- and caspase-based HTS assays as an inducer of apoptosis. Compound 2 is active against cancer cells derived from several human solid tumors, with EC50 values ranging from 400 to 700 nM. SAR study of hit 2 led to the discovery of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as a novel series of potent apoptosis inducers, with 1,3-dimethyl-N-(4-propionylphenyl)-1H-pyrazolo[3,4-b]quinotin-amine (6b) having EC50 values ranging from 30 to 70 nM in cancer cells. These compounds also demonstrated potent activity in the cell growth inhibition assay, with GI(50) values of 16-42 nM for compound 6b. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.046
• 作为产物：
  描述：

  N-(1-ethyl-3-methylpyrazol-5-yl)-anthranilic acid 在 三氯氧磷 作用下， 以6.7 g (95%)的产率得到1-乙基-3-甲基-4-氯-1H-吡唑并[3,4-b]喹啉
  参考文献：
  名称：

  Substituted N-cycloalkylmethyl-1H-pyrazolo(3,4-b)quinolin-4 amines and

  摘要：

  N-环烷基甲基-1H-吡唑并[3,4-b]喹啉-4-胺的替代物，包含它们的药物组合物以及用于a) 作用于c-GMP-磷酸二酯酶抑制，b) 治疗心力衰竭和/或高血压，c) 逆转或减少硝酸盐引起的耐受性和d) 用于治疗心绞痛、充血性心脏病和心肌梗死的方法。

  公开号：

  US05488055A1

文献信息

• Substituted N-cycloalkylmethyl-1H-pyrazolo(3,4-b)quinolin-4 amines and
  申请人：Sanofi Winthrop Inc.

  公开号：US05488055A1

  公开（公告）日：1996-01-30

  Substituted N-cycloalkylmethyl-1H-pyrazolo[3,4-b]quinolin-4-amines, pharmaceutical compositions containing them and methods for a) effecting c-GMP-phosphodiesterase inhibition, b) treating heart failure and/or hypertension, c) reversing or reducing nitrate-induced tolerance and d) treating angina pectoris, congestive heart disease and myocardial infarction utilizing them.

  N-环烷基甲基-1H-吡唑并[3,4-b]喹啉-4-胺的替代物，包含它们的药物组合物以及用于a) 作用于c-GMP-磷酸二酯酶抑制，b) 治疗心力衰竭和/或高血压，c) 逆转或减少硝酸盐引起的耐受性和d) 用于治疗心绞痛、充血性心脏病和心肌梗死的方法。
• Method for inhibiting neoplastic cells by exposure to substituted
  申请人：Cell Pathways, Inc.

  公开号：US05942520A1

  公开（公告）日：1999-08-24

  A method for inhibiting neoplastic cells and related conditions by exposing them to substituted N-cycloalkylmethyl-1H-pyrazolo\x9b3,4-b!quinolin-4-amines.

  通过将肿瘤细胞及相关病况暴露于取代N-环烷甲基-1H-吡唑并[3,4-b]喹啉-4-胺中，来抑制肿瘤细胞及相关病况的方法。
• Substituted N-arylmethyl and
  申请人：Sterling Winthrop Inc.

  公开号：US05614530A1

  公开（公告）日：1997-03-25

  Substituted N-arylmethyl and heterocyclylmethyl-1H-pyrazolo[3,4-b]quinolin-4-amines, pharmaceutical compositions containing them and methods for a) effecting c-GMP-phosphodiesterase inhibition, b) treating heart failure and/or hypertension, c) reversing or reducing nitrate-induced tolerance and d) treating angina pectoris, congestive heart disease and myocardial infarction utilizing them.

  替代N-芳基甲基和杂环基甲基-1H-吡唑并[3,4-b]喹啉-4-胺，含有它们的制药组合物以及使用它们的方法，包括a）影响c-GMP-磷酸二酯酶抑制，b）治疗心力衰竭和/或高血压，c）逆转或减少硝酸盐引起的耐受性和d）治疗心绞痛，充血性心力衰竭和心肌梗塞。
• Substituted N-arylmethyl and heterocyclylmethyl-1H-pyrazolo (3,4-b)
  申请人：Sanofi

  公开号：US05843956A1

  公开（公告）日：1998-12-01

  Substituted N-arylmethyl and heterocyclylmethyl-1H-pyrazolo\x9b3,4-b!quinolin-4-amines, pharmaceutical compositions containing them and methods for a) effecting c-GMP-phosphodiesterase inhibition, b) treating heart failure and/or hypertension, c) reversing or reducing nitrate-induced tolerance and d) treating angina pectoris, congestive heart disease and myocardial infarction utilizing them.

  取代的N-芳基甲基和杂环基甲基-1H-吡唑并[3,4-b]喹啉-4-胺，包含它们的制药组合物以及使用它们的方法：a）影响c-GMP-磷酸二酯酶抑制作用，b）治疗心力衰竭和/或高血压，c）逆转或减少硝酸盐引起的耐受性和d）治疗心绞痛，充血性心脏病和心肌梗死。
• Method for inhibiting neoplastic cells and related conditions by
  申请人：Cell Pathways, Inc.

  公开号：US05852035A1

  公开（公告）日：1998-12-22

  A method for inhibiting neoplastic cells and related conditions by exposing them to substituted N-arylmethyl and heterocyclmethyl-1H-pyrazolo\x9b3,4-B!quinolin-4-amines.

  一种通过将代替N-芳基甲基和杂环甲基-1H-吡唑并[3,4-B]喹啉-4-胺暴露于其上来抑制肿瘤细胞及相关疾病的方法。