3-(噻吩-2-基)-异喹啉-1-基胺 | 1029008-59-0

• 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: 3-(噻吩-2-基)-异喹啉-1-基胺
• 英文名称: 3-(thiophen-2-yl)-isoquinolin-1-ylamine
• 英文别名: 3-(thiophen-2-yl)isoquinolin-1-amine；3-Thiophen-2-ylisoquinolin-1-amine
• CAS: 1029008-59-0
• 化学式: C₁₃H₁₀N₂S
• 分子量: 226.302
• InChiKey: UFZYGGSMDGBXLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 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：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(噻吩-2-基)-异喹啉-1-基胺 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 生成 3-(thiophen-2-yl)-isoquinolin-1-ylamine hydrochloride
  参考文献：
  名称：

  Design, synthesis and systematic evaluation of cytotoxic 3-heteroarylisoquinolinamines as topoisomerases inhibitors

  摘要：

  A series of 3-heteroarylisoquinolinamines were designed, synthesized and evaluated for cytotoxicity, topoisomerases (topos) inhibitory activities and cell cycle inhibition. Several of the 3-heteroarylisoquinolines exhibited selective cytotoxicity against human ductal breast epithelial tumor (T47D) cells over non-cancerous human breast epithelial (MCF-10A) and human prostate cancer (DU145) cells. Most of the derivatives showed greater cytotoxicity in human colorectal adenocarcinoma (HCT-15) cells than camptothecin (CPT), etoposide and doxorubicin (DOX). Generally, 3-heteroarylisoquinolinamines displayed greater affinity for topo I than topo II. 3-Heteroarylisoquinolinamines with greater topo I inhibitory effect exhibited potent cytotoxicity. Piperazine-substituted derivative, 5b, with potent topo land moderate topo II activities intercalated between DNA bases and interacted with topos through H-bonds at the DNA cleavage site of a docking model. Moreover, flow cytometry indicated that cytotoxic 3-heteroarylisoquinolinamines led to accumulation of human cervical (HeLa) cancer cells in the different phases of the cell cycle before apoptosis. Taken together, 3-heteroarylisoquinolinamines possessed potent cytotoxicity with topos and cell cycle inhibitory activities. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.047
• 作为产物：
  描述：

  N,N-二乙基-2-甲基苯甲酰胺 在 ammonium hydroxide 、 正丁基锂 、 碳酸氢钠 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 54.0h， 生成 3-(噻吩-2-基)-异喹啉-1-基胺
  参考文献：
  名称：

  Design, synthesis and systematic evaluation of cytotoxic 3-heteroarylisoquinolinamines as topoisomerases inhibitors

  摘要：

  A series of 3-heteroarylisoquinolinamines were designed, synthesized and evaluated for cytotoxicity, topoisomerases (topos) inhibitory activities and cell cycle inhibition. Several of the 3-heteroarylisoquinolines exhibited selective cytotoxicity against human ductal breast epithelial tumor (T47D) cells over non-cancerous human breast epithelial (MCF-10A) and human prostate cancer (DU145) cells. Most of the derivatives showed greater cytotoxicity in human colorectal adenocarcinoma (HCT-15) cells than camptothecin (CPT), etoposide and doxorubicin (DOX). Generally, 3-heteroarylisoquinolinamines displayed greater affinity for topo I than topo II. 3-Heteroarylisoquinolinamines with greater topo I inhibitory effect exhibited potent cytotoxicity. Piperazine-substituted derivative, 5b, with potent topo land moderate topo II activities intercalated between DNA bases and interacted with topos through H-bonds at the DNA cleavage site of a docking model. Moreover, flow cytometry indicated that cytotoxic 3-heteroarylisoquinolinamines led to accumulation of human cervical (HeLa) cancer cells in the different phases of the cell cycle before apoptosis. Taken together, 3-heteroarylisoquinolinamines possessed potent cytotoxicity with topos and cell cycle inhibitory activities. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.047

文献信息

• 5, 6, or 7-Substituted - 3-(hetero) arylisoquinolinamine derivatives and therapeutic use thereof
  申请人：Lee Young B.

  公开号：US20080182871A1

  公开（公告）日：2008-07-31

  The present invention relates to 5, 6, or 7-substituted-3-(hetero)arylisoquinolinamine derivatives represented by general formula D, their pharmacologically acceptable salts thereof, and compositions containing such compounds. Methods for treating hyperproliferative disorders by administering the compounds are also included.

  本发明涉及一般公式D所代表的5,6或7-取代-3-(杂)芳基异喹啉胺衍生物及其药理学上可接受的盐，以及含有这类化合物的组合物。还包括通过给予这些化合物来治疗过度增殖性疾病的方法。
• 5, 6, or 7-SUBSTITUTED -3-(HETERO) ARYLISOQUINOLINAMINE DERIVATIVES AND THERAPEUTIC USE THEREOF
  申请人：LEE YOUNG B.

  公开号：US20120029012A1

  公开（公告）日：2012-02-02

  The present invention relates to 5, 6, or 7-substituted-3-(hetero)arylisoquinolinamine derivatives represented by general formula D, their pharmacologically acceptable salts thereof, and compositions containing such compounds. Methods for treating hyperproliferative disorders by administering the compounds are also included.

  本发明涉及5、6或7-取代-3-(杂)芳基异喹啉胺衍生物D的一般式，其药理学上可接受的盐以及含有这种化合物的组合物。还包括通过给予这些化合物治疗过度增殖性疾病的方法。
• Alkaline-Metal-Promoted Divergent Synthesis of 1-Aminoisoquinolines and Isoquinolines
  作者：Peng Ma、Yuhang Wang、Ning Ma、Jianhui Wang

  DOI：10.1021/acs.joc.3c02384

  日期：2024.1.19

  Alkaline-metal-promoted divergent syntheses of 1-aminoisoquinolines and isoquinolines have been reported involving 2-methylaryl aldehydes, nitriles, and LiN(SiMe3)2 as reactants. In addition, the three-component reaction of 2-methylaryl nitriles, aldehydes, and LiN(SiMe3)2 has been developed to furnish 1-aminoisoquinolines. This protocol features readily available starting materials, excellent chemoselectivity

  碱金属促进的1-氨基异喹啉和异喹啉的不同合成已被报道，涉及2-甲基芳基醛、腈和LiN(SiMe 3 ) 2作为反应物。此外，还开发了2-甲基芳基腈、醛和LiN(SiMe 3 ) 2的三组分反应以提供1-氨基异喹啉。该方案具有易于获得的起始材料、优异的化学选择性、广泛的底物范围和令人满意的产率。
• 5, 6 or 7-substituted-3-phenylisoquinolinamine derivatives and therapeutic use thereof
  申请人：Rexahn Pharmaceuticals, Inc.

  公开号：EP2423196A1

  公开（公告）日：2012-02-29

  The present invention relates to 5, 6, or 7-substituted-3-(hetero)arylisoquinolinamine derivatives represented by general formula D, their pharmacologically acceptable salts thereof, and compositions containing such compounds. Methods for treating hyperproliferative disorders by administering the compounds are also included.

  本发明涉及通式 D 所代表的 5、6 或 7-取代-3-(杂)芳基异喹啉胺衍生物、其药理学上可接受的盐，以及含有此类化合物的组合物。此外，还包括通过施用这些化合物来治疗过度增殖性疾病的方法。
• 5, 6, OR 7-SUBSTITUTED-3-(HETERO)ARYLISOQUINOLINAMINE DERIVATIVES AS ANTITUMOR AGENTS
  申请人：Rexahn Pharmaceuticals, Inc.

  公开号：EP2099765A2

  公开（公告）日：2009-09-16