1,3-dimethyl-8-nitro-N-(4-propionylphenyl)-1H-pyrazolo[3,4-b]quinolin-4-amine | 884316-79-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dimethyl-8-nitro-N-(4-propionylphenyl)-1H-pyrazolo[3,4-b]quinolin-4-amine
• 英文别名: 1-[4-[(1,3-dimethyl-8-nitropyrazolo[3,4-b]quinolin-4-yl)amino]phenyl]propan-1-one
• CAS: 884316-79-4
• 化学式: C₂₁H₁₉N₅O₃
• 分子量: 389.414
• InChiKey: HIHCQZLUBPTDQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-8-nitro-N-(4-propionylphenyl)-1H-pyrazolo[3,4-b]quinolin-4-amine 以 甲醇 为溶剂， 反应 4.0h， 以to give 12.5 mg (100%) of the title compound的产率得到8-amino-1,3-dimethyl-N-(4-propionylphenyl)-1H-pyrazolo[3,4-b]quinolin-4-amine
  参考文献：
  名称：

  Substituted N-Aryl-1H-Pyrazolo[3,4-B]Quinolin-4-Amines and Analogs as Activators of Caspases and Inducers of Apoptosis

  摘要：

  本发明涉及被取代的N-芳基-1H-吡唑并[3,4-b]喹啉-4-胺及其类似物，其通式表示为（I）：其中Q，Y，Z，R4-R7，X和Ar在此被定义。本发明还涉及发现具有式（I）的化合物是caspase激活剂和凋亡诱导剂的事实。因此，本发明的caspase激活剂和凋亡诱导剂可用于在各种临床情况下诱导细胞死亡，其中发生异常细胞的无控制生长和扩散。

  公开号：

  US20070253957A1
• 作为产物：
  描述：

  4-chloro-1,3-dimethyl-8-nitro-1H-pyrazolo[3,4-b]quinoline 、 4-胺基丙苯酮 在 苯酚 作用下， 以57%的产率得到1,3-dimethyl-8-nitro-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

文献信息

• [EN] SUBSTITUTED N-ARYL-1H-PYRAZOLO[3,4-b]QUINOLIN-4-AMINES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS<br/>[FR] N-ARYL-1H-PYRAZOLO[3,4-B]QUINOLIN-4-AMINES SUBSTITUES ET ANALOGUES UTILISES COMME ACTIVATEURS DE CASPASES ET INDUCTEURS DE L'APOPTOSE
  申请人：CYTOVIA INC

  公开号：WO2006041900A9

  公开（公告）日：2008-12-31
• SUBSTITUTED N-ARYL-1H-PYRAZOLOÝ3,4-b¨QUINOLIN-4-AMINES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS
  申请人：Cytovia, Inc.

  公开号：EP1807426A2

  公开（公告）日：2007-07-18
• [EN] SUBSTITUTED N-ARYL-1H-PYRAZOLO[3,4-b]QUINOLIN-4-AMINES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS<br/>[FR] N -ARYL-1 H -PYRAZOLO[3,4- B ]QUINOLIN-4-AMINES SUBSTITUES ET ANALOGUES UTILISES COMME ACTIVATEURS DE CASPASES ET INDUCTEURS DE L'APOPTOSE
  申请人：CYTOVIA INC

  公开号：WO2006041900A2

  公开（公告）日：2006-04-20

  The present invention is directed to substituted N-aryl-1H-pyrazolo[3,4-b]quinolin-4-amines and analogs thereof, represented by the general Formula (I): wherein Q, Y, Z, R4-R7, X and Ar are defined herein. The present invention also relates to the discovery that compounds having Formula (I) are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.