N-(2-bromoethyl)pyrazine-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(2-bromoethyl)pyrazine-2-carboxamide
• 英文别名: 2-(pyrazinamido)-1-bromoethane；Pyrazine-2-carboxylic acid (2-bromo-ethyl)-amide；pyrazine-2-carboxylic acid (2-bromoethyl)amide
• 化学式: C₇H₈BrN₃O
• 分子量: 230.064
• InChiKey: GNCYSRAVJDPFJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-3-{[(1-phenylcycloheptyl)carbonyl]oxy}-1-azabicyclo[2.2.2]octane 、 N-(2-bromoethyl)pyrazine-2-carboxamide 在 乙腈 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以to give the title compound (96 mg) as a white solid的产率得到(R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-{2-[(pyrazine-2-carbonyl)-amino]-ethyl}-1-azonia-bicyclo[2.2.2]octane bromide
  参考文献：
  名称：

  QUINUCLIDINE DERIVATIVES AS MUSCARINIC M3 RECEPTOR ANTAGONISTS

  摘要：

  本发明提供了式（I）的命名化合物，其中R4是N-取代的喹诺啉（I），还提供了含有这些化合物的药物组合物以及制备药物组合物的过程。本发明还揭示了它们在治疗由M3胆碱能受体介导的疾病，如慢性阻塞性肺疾病中的应用。

  公开号：

  US20110172237A1
• 作为产物：
  描述：

  2-甲酸吡嗪 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 N-(2-bromoethyl)pyrazine-2-carboxamide
  参考文献：
  名称：

  Design, synthesis and biological activity of pyrazinamide derivatives for anti-Mycobacterium tuberculosis

  摘要：

  A total of 11 pyrazinamide derivatives were designed and synthesised using pyrazinamide as the lead compound, which was optimised by structural modification with alkyl chains, six-membered rings, and bioisosterism, respectively. The target compounds were synthesised using pyrazinecarboxylic acid as the starting material by acylation, amidation, and alkylation, respectively. Their structures were confirmed by H-1 NMR, C-13 NMR, HRESIMS, and elemental analysis, respectively. The bioactivities of derivatives were assayed using bacteriostatic experiment and minimum inhibitory concentration experiment. It was showed that the derivatives had good inhibitory effect on Mycobacterium tuberculosis. The biological activity of derivative 1f was the best among all compounds, its antibacterial activity was 99.6%, and the minimum inhibitory concentration was 8.0 mu g/mL.

  DOI：

  10.1080/14756366.2017.1367774

文献信息

• Quinuclidine derivatives as muscarinic M3 receptor antagonists
  申请人：Astrazeneca AB

  公开号：US08329729B2

  公开（公告）日：2012-12-11

  The invention provides named compounds of formula (I), wherein R4 is a N-substituted quinuclidine (I) pharmaceutical compositions containing them and a process for preparing the pharmaceutical compositions. Their use in therapy for the treatment of conditions mediated by M3 muscarinic receptors, such as chronic obstructive pulmonary disease is also disclosed.

  该发明提供了式(I)的命名化合物，其中R4是一种N-取代的喹诺啉，还提供了含有这些化合物的制药组合物以及制备制药组合物的过程。还披露了它们在治疗由M3胆碱能受体介导的疾病，如慢性阻塞性肺疾病的用途。
• [EN] QUINUCLIDINE DERIVATIVES AS MUSCARINIC M3 RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS DE QUINUCLIDINE UTILISÉS COMME ANTAGONISTES DES RÉCEPTEURS MUSCARINIQUES M3
  申请人：ASTRAZENECA AB

  公开号：WO2009138707A9

  公开（公告）日：2010-01-28
• Novel fluoroquinolones: design, synthesis, and in vivo activity in mice against Mycobacterium tuberculosis H37Rv
  作者：Anand V. Shindikar、C.L. Viswanathan

  DOI：10.1016/j.bmcl.2005.02.037

  日期：2005.4

  Novel 6,8-difluoro-1-alkyl-5-amino-1,4-dihydro-4-oxo-7-4-substituted piperazin-1-yl}-quinoline-3-carboxylic acids, with the substituents at 4th position of piperazine being -[2(pyridine-4-carbonyl) hydrazono]propyl and -2[(pyrazine-2-carbonyl) amino] ethyl, were synthesized and evaluated in vivo against Mycobacterium tuberculosis H(37)Rv in Swiss albino mice. Test compounds exhibited activity comparable to that of sparfloxacin (survival rate, reduction of splenomegaly and reduced tubercular lesions) at a dose of 200 mg/kg. (c) 2005 Elsevier Ltd. All rights reserved.
• US8329729B2
  申请人：——

  公开号：US8329729B2

  公开（公告）日：2012-12-11
• QUINUCLIDINE DERIVATIVES AS MUSCARINIC M3 RECEPTOR ANTAGONISTS
  申请人：Bull Richard James

  公开号：US20110172237A1

  公开（公告）日：2011-07-14

  The invention provides named compounds of formula (I), wherein R4 is a N-substituted quinuclidine (I) pharmaceutical compositions containing them and a process for preparing the pharmaceutical compositions. Their use in therapy for’ the treatment of conditions mediated by M3 muscarinic receptors, such as chronic obstructive pulmonary disease is also disclosed.

  这项发明提供了式(I)的命名化合物，其中R4是N-取代的喹啉啶(I)药物组合物以及制备药物组合物的方法。还披露了它们在治疗由M3胆碱能受体介导的疾病，如慢性阻塞性肺病中的用途。