4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]quinoline | 24158-31-4

• 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: 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]quinoline
• 英文别名: 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]quinoline；1,3-dimethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline；4-Chloro-1,3-dimethyl-1H-pyrazolo<3,4-b>quinoline；4-chloro-1,3-dimethylpyrazolo[3,4-b]quinoline
• CAS: 24158-31-4
• 化学式: C₁₂H₁₀ClN₃
• 分子量: 231.685
• InChiKey: CLRNUDVGJVDYTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 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

• 作为反应物：
  描述：

  4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]quinoline 在 盐酸 作用下， 反应 2.0h， 以81%的产率得到4,9-dihydro-1,3-dimethyl-4-oxo-1H-pyrazolo<3,4-b>quinoline
  参考文献：
  名称：

  Syntheses of 1, 2, and 9-methyl derivatives of 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and their antiviral activity

  摘要：

  这篇论文描述了4,9-二氢-3-甲基-4-氧代-1H(2H)-吡唑并[3,4-b]喹啉(Ia)、它的1-甲基衍生物(Ib)、2-甲基衍生物(IIa)、9-甲基衍生物(Ic)、1,9-二甲基衍生物(Id)和2,9-二甲基衍生物(IIb)的合成方法。化合物Ia、Ib、Ic和IIa的钠盐在室温下用碘甲烷在二甲基甲酰胺中甲基化，化合物Id和IIb则用盐酸吡啶脱甲基。制备的化合物在小鼠体内针对甲型流感病毒A2-香港和脑心肌病毒进行了抗病毒活性测试。

  DOI：

  10.1135/cccc19851057
• 作为产物：
  描述：

  2-[(1,3-二甲基-1H-吡唑-5-基)氨基]苯甲酸 在 三氯氧磷 作用下， 生成 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]quinoline
  参考文献：
  名称：

  Substituted N-arylmethyl and

  摘要：

  含有取代N-芳基甲基和杂环甲基-1H-吡唑并[3,4-b]喹啉-4-胺的药物组合物，以及用于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）逆转或减少硝酸盐诱导的耐受性和d）治疗心绞痛、充血性心力衰竭和心肌梗死的方法。

  公开号：

  US05614530A1

文献信息

• 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.

  通过将肿瘤细胞及相关病况暴露于取代的N-芳基甲基和杂环甲基-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。
• Interferon inducing activities of derivatives of 1,3-dimethyl-4-(3-dimethylaminopropylamino)-1H-pyrazolo[3,4-b]quinoline and related compounds
  作者：R. R. Crenshaw、George M. Luke、Paul Siminoff

  DOI：10.1021/jm00224a013

  日期：1976.2

  zolo[3,4-b]quinoline (1). Three different generalized synthetic schemes for the preparation of pyrazolo[3,4-b]quinolines are presented and limitations contrasted. Other heterocyclic nuclei containing the 3-dimethylaminopropylamino side chain include pyridine, quinoline, acridine, pyrazolo[3,4-b]pyridine, pyrazolo[3,4-B][1,8]naphthyridine, pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidine, dipyrazolo[3,4-b:4'

  据报道有137位亲属的1,3-二甲基-4-（3-二甲基氨基-丙基氨基）-1H-吡唑并[3,4-b]喹啉的合成和诱导干扰素的活性（1）。介绍了三种不同的制备吡唑并[3,4-b]喹啉的通用合成方案，并比较了其局限性。含有3-二甲基氨基丙基氨基侧链的其他杂环核包括吡啶，喹啉，a啶，吡唑并[3,4-b]吡啶，吡唑并[3,4-B] [1,8]萘啶，吡唑并[4'，3'： 5,6]吡啶并[2,3-d]嘧啶，吡唑并[3,4-b：4'，3'-e]吡啶，吡咯并[[2,3-b]喹啉，异噻唑并[5,4-b ]喹啉和吡啶并[2,3-h]吡唑并[3,4-b]喹啉。讨论了该系列中干扰素诱导的结构要求，并将其中两种更具活性的化合物（172和196）直接与替罗酮进行了比较。
• 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。
• Substituted N-Aryl-1H-Pyrazolo[3,4-B]Quinolin-4-Amines and Analogs as Activators of Caspases and Inducers of Apoptosis
  申请人：Zhang Han-Zhong

  公开号：US20070253957A1

  公开（公告）日：2007-11-01

  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, R 4 -R 7 , 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.

  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。
• Discovery and structure–activity relationship of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as a new series of potent apoptosis inducers
  作者：Han-Zhong Zhang、Gisela Claassen、Candace Crogran-Grundy、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmc.2007.09.046

  日期：2008.1

  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.