3-(thiophen-2-yl)isoquinolin-1(2H)-one | 82537-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-(thiophen-2-yl)isoquinolin-1(2H)-one
• 英文别名: Thienyl-isoquinolone；3-thiophen-2-yl-2H-isoquinolin-1-one
• CAS: 82537-17-5
• 化学式: C₁₃H₉NOS
• 分子量: 227.287
• InChiKey: JQNLAHXVJMWJKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(thiophen-2-yl)isoquinolin-1(2H)-one 在 三氯氧磷 作用下， 以66%的产率得到1-chloro-3-thiophen-2-yl-isoquinoline
  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：

  2-乙酰基噻吩 、 2-溴苯甲酰胺 在 caesium carbonate 、 copper(I) bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以88%的产率得到3-(thiophen-2-yl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  铜与2-卤代苯甲酰胺酮催化α-芳基化反应合成功能化异喹啉-1（2H）-酮

  摘要：

  铜是关键：有效的铜催化酮与2-卤代苯甲酰胺的环合反应可提供从简单易得的起始原料到异喹啉-1（2 H）-one的简捷途径。该方法适用于范围广泛的含有不同官能团的酮，从而以中等至极好的收率提供了产品。

  DOI：

  10.1002/chem.201301621

文献信息

• [EN] THIENYL- AND FURANYL-ISOQUINOLINONES AND METHODS FOR USING THEM<br/>[FR] THIÉNYL-ISOQUINOLINONES ET FURANYL-ISOQUINOLINONES, ET LEURS PROCÉDÉS D'UTILISATION
  申请人：WYETH CORP

  公开号：WO2009155413A1

  公开（公告）日：2009-12-23

  The present invention relates to substituted thienyl- and furanyl- isoquinolinones that act, for example, as modulators of poly(ADP-ribose) polymerase (PARP). The present invention also relates to processes for the preparation of substituted thienyl and furanyl-isoquinolinones and to their use in treating various diseases and disorders.

  本发明涉及替代噻吩基和呋喃基异喹啉酮，例如作为多聚腺苷二磷酸核糖聚合酶（PARP）的调节剂。本发明还涉及替代噻吩基和呋喃基异喹啉酮的制备方法，以及它们在治疗各种疾病和疾病中的应用。
• Convenient preparation of 3-substituted 1(2H)-isoquinolinones
  作者：Graham S. Poindexter

  DOI：10.1021/jo00140a047

  日期：1982.9
• Kaneko, Chikara; Naito, Toshihiko; Miwa, Chiemi, Heterocycles, 1984, vol. 21, # 2, p. 405
  作者：Kaneko, Chikara、Naito, Toshihiko、Miwa, Chiemi、Ohashi, Testuo

  DOI：——

  日期：——
• THIENYL- AND FURANYL-ISOQUINOLINONES AND METHODS FOR USING THEM
  申请人：Wyeth LLC

  公开号：EP2313418A1

  公开（公告）日：2011-04-27
• CN115403591
  申请人：——

  公开号：——

  公开（公告）日：——