1,3-二甲基吡唑并[3,4-b]喹啉 | 89522-26-9

• 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: 1,3-二甲基吡唑并[3,4-b]喹啉
• 英文名称: 1,3-dimethyl-1H-pyrazolo[3,4-b]quinoline
• 英文别名: 1,3-dimethylpyrazolo[3,4-b]quinoline
• CAS: 89522-26-9
• 化学式: C₁₂H₁₁N₃
• 分子量: 197.239
• InChiKey: JZDPNYXRLMYHLU-UHFFFAOYSA-N

物化性质

• 沸点：
  372.6±22.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4Z)-4-[(2-aminophenyl)methylidene]-2,5-dimethylpyrazol-3-one 以100%的产率得到
  参考文献：
  名称：

  TOMASIK, D.;TOMASIK, P.;ABRAMOVITCH, R. A., J. HETEROCYCL. CHEM., 1983, 20, N 6, 1539-1543

  摘要：

  DOI：

文献信息

• Facile and Regioselective Synthesis of Substituted 1<i>H</i>‐Pyrazolo[3,4‐<i>b</i>]quinolines from 2‐Fluorobenzaldehydes and 1<i>H</i>‐Pyrazol‐5‐amines
  作者：Paweł Szlachcic、Mateusz Kucharek、Bożena Jarosz、Andrzej Danel、Katarzyna Stadnicka

  DOI：10.1002/jhet.2751

  日期：2017.5

  The present article concerns the scope and limitations of the regioselective condensation of 2‐fluorobenzaldehydes with 1H‐pyrazol‐5‐amines, leading to the synthesis of substituted 1H‐pyrazolo[3,4‐b]quinolines (PQ), in the presence of a base catalyst (DABCO and 2,4,6‐trimethylpyridine). A method to obtain these nitrogen heterocycles with fluorine or trifluoromethyl substituents in different positions

  本文涉及2-氟苯甲醛与1 H-吡唑-5-胺的区域选择性缩合的范围和局限性，导致取代的1 H-吡唑并[3,4- b ]喹啉（PQ）的合成。存在碱催化剂（DABCO和2,4,6-三甲基吡啶）。系统地研究了含氟取代基对PQ参数的影响，研究了一种获得碳环上不同位置具有氟或三氟甲基取代基的氮杂环的方法。的那些化合物，其特征在于高的荧光强度，经测试作为发光体的有机发光二极管自1997年以来的官能PQ引起各种参数的变化，例如，HOMO和LUMO能级，这对调整重要人造有机发光二极管。PQ制备最简单的方法之一，即取代的苯胺与5-氯-1 H-吡唑-4-甲醛的缩合反应不是区域选择性的。这项研究中描述的方法可以合成1 H吡唑并[3,4- b具有高收率和高选择性的]喹啉–仅获得预期的异构体。由于可以从市场上购买到各种不同的2-氟苯甲醛，并且易于制备具有不同取代基的1 H-吡唑-5-胺，因此该方法可以替代已知方法。还详细研究了反应的所有可能机理。
• [EN] 4-AMINOQUINOLINE COMPOUNDS<br/>[FR] COMPOSES 4-AMINOQUINOLEINES
  申请人：MERCK & CO INC

  公开号：WO2003045920A1

  公开（公告）日：2003-06-05

  The present invention is concerned with compounds of the general Formula I : and pharmaceutically acceptable salts thereof, which are useful as melanin concentrating hormone receptor antagonists, particularly MCH-1R antagonists. As such, compounds of the present invention are useful for the treatment or prevention of obesity or eating disorders associated with excessive food intake and complications thereof, osteoarthritis, certain cancers, AIDS wasting, cachexia, frailty (particularly in elderly), mental disorders stress, cognitive disorders, sexual function, reproductive function, kidney function, locomotor disorders, attention deficit disorder (ADD), substance abuse disorders and dyskinesias, Huntington s disease, epilepsy, memory function, and spinal muscular atrophy. Compounds of formula I may therefore be used in the treatment of these conditions, and in the manufacture of a medicament useful in treating these conditions. Pharmaceutical formulations comprising one of the compounds of formula (I) as an active ingredient are disclosed, as are processes for preparing these compounds.

  本发明涉及一般式I的化合物及其药学上可接受的盐，这些化合物可用作黑色素浓集激素受体拮抗剂，尤其是MCH-1R拮抗剂。因此，本发明的化合物可用于治疗或预防与过度进食及其并发症相关的肥胖症或进食障碍、骨关节炎、某些癌症、艾滋病消耗症、消瘦、虚弱（尤其是老年人）、心理障碍、压力、认知障碍、性功能、生殖功能、肾功能、运动障碍、注意力缺陷障碍（ADD）、物质滥用障碍和运动障碍、亨廷顿病、癫痫、记忆功能和脊髓肌萎缩症。因此，I式化合物可用于治疗这些疾病，并用于制造用于治疗这些疾病的药物。本发明披露了包含一种I式化合物作为活性成分的制药配方，以及制备这些化合物的过程。
• 4-Aminoquinoline compounds
  申请人：DeVita J. Robert

  公开号：US20050009815A1

  公开（公告）日：2005-01-13

  The present invention is concerned with compounds of the general Formula I: and pharmaceutically acceptable salts thereof, which are useful as melanin concentrating hormone receptor antagonists, particularly MCH-1R antagonists. As such, compounds of the present invention are useful for the treatment or prevention of obesity or eating disorders associated with excessive food intake and complications thereof, osteoarthritis, certain cancers, AIDS wasting, cachexia, frailty (particularly in elderly), mental disorders stress, cognitive disorders, sexual function, reproductive function, kidney function, locomotor disorders, attention deficit disorder (ADD), substance abuse disorders and dyskinesias, Huntington's disease, epilepsy, memory function, and spinal muscular atrophy. Compounds of formula I may therefore be used in the treatment of these conditions, and in the manufacture of a medicament useful in treating these conditions. Pharmaceutical formulations comprising one of the compounds of formula (I) as an active ingredient are disclosed, as are processes for preparing these compounds.

  本发明涉及一般式I的化合物及其药用可接受的盐，其作为黑色素浓集激素受体拮抗剂，特别是MCH-1R拮抗剂，具有用途。因此，本发明的化合物可用于治疗或预防与过度进食及其并发症相关的肥胖症或进食障碍、骨关节炎、某些癌症、艾滋病消耗综合征、恶病质、虚弱（特别是老年人）、心理障碍、压力、认知障碍、性功能、生殖功能、肾功能、运动障碍、注意力缺陷障碍（ADD）、物质滥用障碍和运动障碍、亨廷顿病、癫痫、记忆功能和脊髓肌萎缩症。因此，式I的化合物可用于治疗这些疾病，并用于制造用于治疗这些疾病的药物。本发明还揭示了包含式（I）的化合物作为活性成分的制药配方，以及制备这些化合物的过程。
• 2-Aminoquinoline compounds
  申请人：DeVita J. Robert

  公开号：US20050026915A1

  公开（公告）日：2005-02-03

  The present invention is concerned with compounds of the general Formula I: and pharmaceutically acceptable salts thereof, which are useful as melanin concentrating hormone receptor antagonists, particularly MCH-1R antagonists. As such, compounds of the present invention are useful for the treatment or prevention of obesity or eating disorders associated with excessive food intake and complications thereof, osteoarthritis, certain cancers, AIDS wasting, cachexia, frailty (particularly in elderly), mental disorders stress, cognitive disorders, sexual function, reproductive function, kidney function, locomotor disorders, attention deficit disorder (ADD), substance abuse disorders and dyskinesias, Huntington's disease, epilepsy, memory function, and spinal muscular atrophy. Compounds of formula I may therefore be used in the treatment of these conditions, and in the manufacture of a medicament useful in treating these conditions. Pharmaceutical formulations comprising one of the compounds of formula (I) as an active ingredient are disclosed, as are processes for preparing these compounds.

  本发明涉及一般式I的化合物及其药学上可接受的盐，其作为黑色素浓集激素受体拮抗剂，特别是MCH-1R拮抗剂而有用。因此，本发明的化合物可用于治疗或预防与过度食物摄入及其并发症有关的肥胖症或进食障碍，骨关节炎，某些癌症，艾滋病消耗症，消瘦，衰弱（尤其是老年人），精神障碍，压力，认知障碍，性功能，生殖功能，肾功能，运动障碍，注意力缺陷障碍（ADD），物质滥用障碍和运动障碍，亨廷顿病，癫痫，记忆功能和脊髓肌萎缩。因此，式I的化合物可用于治疗这些疾病，并用于制造用于治疗这些疾病的药物。本发明还公开了包含式（I）中的一种化合物作为活性成分的制药配方，以及制备这些化合物的过程。
• A simple and efficient synthesis of 1,3,6-trisubstituted pyrazoloquinolines via intramolecular cyclization – optimization studies
  作者：Mateusz Kucharek、Andrzej Danel、Arkadiusz Gut

  DOI：10.1007/s10593-022-03127-1

  日期：2022.11

  In this work, we developed a straightforward and convenient method for the synthesis of substituted pyrazoloquinolines – highly desirable compounds for many high-tech and biomedical applications. On the basis of intramolecular cyclization of 5-(N-aryl)aminopyrazoles in the presence of DMF diethyl acetal and POCl3, a series of differently substituted pyrazoloquinolines were synthesized. The synthetic

  在这项工作中，我们开发了一种简单方便的方法来合成取代的吡唑并喹啉——许多高科技和生物医学应用中非常理想的化合物。以5-( N-芳基)氨基吡唑在DMF二乙缩醛和POCl 3存在下的分子内环化为基础，合成了一系列不同取代的吡唑并喹啉。考虑到甲酰化剂的类型（DMF与. DMF 二乙基二缩醛）、反应温度和所用试剂的化学计量。由于其多功能性、简单性和易于纯化获得的产品，这种合成方法为吡唑并喹啉基功能材料的合理设计提供了有价值的指导。