N-(7-chloro-2,3-dimethoxy-6-methylquinoxalin-5-yl)methanesulphonamide | 178907-41-0

• 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: N-(7-chloro-2,3-dimethoxy-6-methylquinoxalin-5-yl)methanesulphonamide
• 英文别名: N-(7-chloro-2,3-dimethoxy-6-methylquinoxalin-5-yl)methanesulfonamide
• CAS: 178907-41-0
• 化学式: C₁₂H₁₄ClN₃O₄S
• 分子量: 331.78
• InChiKey: IAZGGSYGHYSCCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(7-chloro-2,3-dimethoxy-6-methylquinoxalin-5-yl)methanesulphonamide 在 盐酸 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 N-(7-chloro-6-methyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-N-(2-methoxyethyl)methanesulfonamide
  参考文献：
  名称：

  N-(6,7-Dichloro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-N-alkylsulfonamides as peripherally restricted N-methyl-d-aspartate receptor antagonists for the treatment of pain

  摘要：

  It has been hypothesized that peripherally restricted NMDA receptor antagonists may be effective analgesics for osteoarthritis pain. A class of novel quinoxalinedione atropisomers, first discovered for an NMDA receptor antagonist program for the treatment of stroke, was evaluated and further optimized with the goal of finding peripherally restricted NMDA receptor antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.083
• 作为产物：
  描述：

  5-Amino-7-chloro-2,3-dimethoxy-6-methylquinoxaline 在 吡啶 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 N-(7-chloro-2,3-dimethoxy-6-methylquinoxalin-5-yl)methanesulphonamide
  参考文献：
  名称：

  N-(6,7-Dichloro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-N-alkylsulfonamides as peripherally restricted N-methyl-d-aspartate receptor antagonists for the treatment of pain

  摘要：

  It has been hypothesized that peripherally restricted NMDA receptor antagonists may be effective analgesics for osteoarthritis pain. A class of novel quinoxalinedione atropisomers, first discovered for an NMDA receptor antagonist program for the treatment of stroke, was evaluated and further optimized with the goal of finding peripherally restricted NMDA receptor antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.083

文献信息

• Quinoxaline derivatives useful in therapy
  申请人：Pfizer, Inc.

  公开号：US05863917A1

  公开（公告）日：1999-01-26

  The invention provides compounds of formula I, ##STR1## wherein R.sup.1 and R.sup.2 independently represent Cl or C.sub.1-6 alkyl; R.sup.3 represents XCO.sub.2 R.sup.4, XCONHSO.sub.2 R.sup.5, YNHSO.sub.2 R.sup.5 or XR.sup.6 ; R.sup.4 represents H or C.sub.1-6 alkyl (optionally substituted by aryl or heterocyclyl); R.sup.5 represents CF.sub.3, heterocyclyl or C.sub.1-6 alkyl (optionally substituted by aryl or heterocyclyl); R.sup.6 represents an acidic heterocycle; X represents a C.sub.1-6 alkyl diradical (optionally subsituted by aryl or heterocyclyl); and Y represents a C.sub.2-6 alkyl diradical (optionally substituted by aryl or heterocyclyl); provided that when R.sup.1 and R.sup.2 each represent Cl, then R.sup.3 does not represent CH.sub.2 CO.sub.2 H, CH.sub.2 CO.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 NHSO.sub.2 CF.sub.3 or 5-tetrazolylmethyl; and pharmaceutically acceptable salts thereof. The compounds are indicated as anxiolytics, anticonvulsants, analgesics and neuroprotectives.

  该发明提供了一种式为I的化合物，其中R.sup.1和R.sup.2独立地代表Cl或C.sub.1-6烷基；R.sup.3代表XCO.sub.2R.sup.4，XCONHSO.sub.2R.sup.5，YNHSO.sub.2R.sup.5或XR.sup.6；R.sup.4代表H或C.sub.1-6烷基（可选择地被芳基或杂环烷基取代）；R.sup.5代表CF.sub.3，杂环烷基或C.sub.1-6烷基（可选择地被芳基或杂环烷基取代）；R.sup.6代表酸性杂环；X代表C.sub.1-6烷基二自由基（可选择地被芳基或杂环烷基取代）；Y代表C.sub.2-6烷基二自由基（可选择地被芳基或杂环烷基取代）；前提是当R.sup.1和R.sup.2均代表Cl时，R.sup.3不代表CH.sub.2CO.sub.2H，CH.sub.2CO.sub.2CH.sub.3，CH.sub.2CH.sub.2NHSO.sub.2CF.sub.3或5-四唑甲基；以及其药学上可接受的盐。这些化合物被指示为抗焦虑剂，抗癫痫剂，镇痛剂和神经保护剂。
• QUINOXALINE DERIVATIVES USEFUL IN THERAPY
  申请人：Pfizer Limited

  公开号：EP0783495B1

  公开（公告）日：2002-02-27
• US5852016A
  申请人：——

  公开号：US5852016A

  公开（公告）日：1998-12-22
• US5863917A
  申请人：——

  公开号：US5863917A

  公开（公告）日：1999-01-26
• [EN] QUINOXALINE DERIVATIVES USEFUL IN THERAPY<br/>[FR] DERIVES DE QUINOXALINE UTILES EN THERAPIE
  申请人：PFIZER LIMITED

  公开号：WO1996009295A1

  公开（公告）日：1996-03-28

  (EN) Compounds of formula (I), wherein A represents N or CH; R1 and R2 independently represent C1-4 alkyl, halo or CF3; R3 represents C1-4 alkyl (optionally substituted), C3-7 cycloalkyl, CF3 or aryl; and R4 represents H, C3-7 cycloalkyl or C1-6 alkyl (optionally substituted); and their pharmaceutically acceptable derivatives; are useful in the treatment of, $i(inter alia), neurodogenerative disorders.(FR) Composés de la formule (I), ainsi que leurs dérivés acceptables sur le plan pharmacologique, dans laquelle A représente N ou CH; R1 et R2 représentent indépendamment alkyle C1-4, halo ou CF3; R3 représente alkyle C1-4 (éventuellement substitué), cycloalkyle C3-7, CF3 ou aryle; et R4 représente H, cycloalkyle C3-7 ou alkyle C1-6 (éventuellement substitué). Ces composés sont utiles dans le traitement, entre autres, des affections dégénératives neuronales.