ethyl N-(6-chloro-2-methoxyquinoxalin-3-yl)carbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl N-(6-chloro-2-methoxyquinoxalin-3-yl)carbamate
• 英文别名: ethyl N-(7-chloro-3-methoxyquinoxalin-2-yl)carbamate
• 化学式: C₁₂H₁₂ClN₃O₃
• 分子量: 281.699
• InChiKey: MPUTUGADEHXZDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-(6-chloro-2-methoxyquinoxalin-3-yl)carbamate 、 1-(3,5-二甲基苯基)哌嗪 以to obtain the titled compound (yield, 79%)的产率得到1-[(6-chloro-2-methoxyquinoxalin-3-yl)aminocarbonyl]-4-(3,5-dimethylphenyl)piperazine
  参考文献：
  名称：

  1-[(6,7-substituted alkoxyquinoxalinyl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives for treating tumors

  摘要：

  本发明涉及新型喹喔啉-哌嗪化合物，式（1）的1-[(6,7-取代烷氧基喹喔啉基)氨基甲酰基]-4-(杂)芳基哌嗪衍生物及其药学上可接受的盐，其制备方法以及含有这些化合物的组合物。本发明还包括通过给予喹喔啉-哌嗪化合物治疗增殖过度性疾病，包括癌症的治疗方法。

  公开号：

  US08598173B2
• 作为产物：
  描述：

  3-amino-6-chloro-2-methoxyquinoxaline 、 氯甲酸乙酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 ethyl N-(6-chloro-2-methoxyquinoxalin-3-yl)carbamate
  参考文献：
  名称：

  Synthesis and anticancer activity of new 1-[(5 or 6-substituted 2-alkoxyquinoxalin-3-yl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives

  摘要：

  A series of novel quinoxalinyl-piperazine compounds, 1-[(5 or 6-substituted alkoxyquinoxalinyl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives were synthesized and evaluated as an anticancer agent. From screening of quinoxalinyl-piperazine compound library, we identified that many compounds inhibited proliferation of various human cancer cells at nanomolar concentrations. Among them, one of the fluoro quinoxalinyl-piperazine derivatives showed its IC(50) values ranging from 11 to 21 nM in the growth inhibition of cancer cells. This compound also displayed a more potent effect than paclitaxel against paclitaxel resistant HCT-15 colorectal carcinoma cells. The potency of this novel compound was further confirmed with the synergistic cytotoxic effect with several known cancer drugs such as paclitaxel, doxorubicin, cisplatin, gemcitabine or 5-fluorouracil in cancer cells. This strong cell killing effect was derived from the induction of apoptosis. Mechanistic studies have shown that this quinoxalinyl-piperazine compound is a G2/M-specific cell cycle inhibitor and inhibits anti-apoptotic Bcl-2 protein with p21 induction. Thus the results suggest that our compound has potential use in the growth inhibition of drug resistant cancer cells and the combination therapy with other clinically approved anticancer agents as well. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.028

文献信息

• 1-[6,7-Substituted Alkoxyquinoxalinyl) Aminocarbonyl]-4-(Hetero) Arylpiperazine Derivatives
  申请人：Gong Young-Dae

  公开号：US20080318963A1

  公开（公告）日：2008-12-25

  The present invention relates to novel quinoxaline-piperazine compounds, 1-[(6,7-substituted alkoxyquinoxalinyl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives and their pharmaceutically acceptable salts, a process for their preparation thereof, and compositions containing such compounds. Therapeutic methods for the treatment of hyperproliferative disorders, including cancers, by administering quinoxalin-piperazine compounds are also included.

  本发明涉及新型喹啉-哌嗪化合物，1-[(6,7-取代烷氧基喹啉基)氨基甲酰基]-4-(杂)芳基哌嗪衍生物及其药学上可接受的盐，以及制备这些化合物的方法和含有这些化合物的组合物。本发明还包括通过给予喹啉-哌嗪化合物治疗增殖性疾病，包括癌症的治疗方法。
• 1-[6,7-substituted alkoxyquinoxalinyl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives
  申请人：Rexahn Pharmaceuticals, Inc.

  公开号：US08314100B2

  公开（公告）日：2012-11-20

  The present invention related to a novel urea derivative for formula (I): which is useful as an anti-cancer agent, its pharmaceutically acceptable acid addition salt or stereoisomer, and to a process for preparing the urea derivative and an anti-cancer composition comprising the same as an active ingredient.

  本发明涉及一种新的尿素衍生物，化学式为(I)，其可用作抗癌剂，其药学上可接受的酸盐或立体异构体，以及制备该尿素衍生物的方法和包含其作为活性成分的抗癌组合物。
• 1-[(6,7-SUBSTITUTED ALKOXYQUINOXALINYL)AMINOCARBONYL]-4-(HETERO)ARYLPIPERAZINE DERIVATIVES
  申请人：Korea Research Institute of Chemical Technology

  公开号：US20130053390A1

  公开（公告）日：2013-02-28

  The present invention relates to novel quinoxaline-piperazine compounds, 1-[(6,7-substituted alkoxyquinoxalinyl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives and their pharmaceutically acceptable salts, a process for their preparation thereof, and compositions containing such compounds. Therapeutic methods for the treatment of hyperproliferative disorders, including cancers, by administering quinoxaline-piperazine compounds are also included.

  本发明涉及新型喹喔啉-哌嗪化合物，1-[(6,7-取代烷氧基喹喔啉基)氨基甲酰基]-4-(杂)芳基哌嗪衍生物及其药学上可接受的盐，以及其制备方法和含有这样的化合物的组合物。本发明还包括通过给予喹喔啉-哌嗪化合物治疗增殖性疾病，包括癌症的治疗方法。
• 1-[(6,7-substituted alkoxyquinoxalinyl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives for treating tumors
  申请人：Korea Research Institute of Chemical Technology

  公开号：US08598173B2

  公开（公告）日：2013-12-03

  The present invention relates to novel quioxaline-piperazine compounds, 1-[(6,7-substituted alkoxyquinoxalinyl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives of formula (1): and their pharmaceutically acceptable salts, a process for their preparation thereof, and compositions containing such compounds. Therapeutic methods for the treatment of hyperproliferative disorders, including cancers, by administering quioxalin-piperazine compounds are also included.

  本发明涉及新型喹喔啉-哌嗪化合物，式（1）的1-[(6,7-取代烷氧基喹喔啉基)氨基甲酰基]-4-(杂)芳基哌嗪衍生物及其药学上可接受的盐，其制备方法以及含有这些化合物的组合物。本发明还包括通过给予喹喔啉-哌嗪化合物治疗增殖过度性疾病，包括癌症的治疗方法。
• WO2006/54830
  申请人：——

  公开号：——

  公开（公告）日：——