1-Carboxymethyl-6-chloroquinoxaline-2,3(1H,4H)-dione | 137689-91-9

• 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: 1-Carboxymethyl-6-chloroquinoxaline-2,3(1H,4H)-dione
• 英文别名: 2-(6-chloro-2,3-dioxo-4H-quinoxalin-1-yl)acetic acid
• CAS: 137689-91-9
• 化学式: C₁₀H₇ClN₂O₄
• 分子量: 254.63
• InChiKey: RMUKGMQTZWIWED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻,对甲苯磺酰胺 、 1-Carboxymethyl-6-chloroquinoxaline-2,3(1H,4H)-dione 在 N,N'-羰基二咪唑 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Lead discovery of quinoxalinediones as an inhibitor of dipeptidyl peptidase-IV (DPP-IV) by high-throughput screening

  摘要：

  N-Ureido-quinoxalinedione derivatives have been discovered as leads for a novel series of dipeptidyl peptidase-IV (DPP-IV) inhibitors through high-throughput screening of our chemical library. A brief structure-activity relationship of the compounds was investigated. Among them, entry 5 showed the most potent inhibitory activity. The nitro group in quinoxaline moiety and the aromatic sulfonyl substituted ureido functional group seem to be important to increase the potency dramatically. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.02.065
• 作为产物：
  描述：

  4-氯-1,2-苯二胺 在 盐酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-Carboxymethyl-6-chloroquinoxaline-2,3(1H,4H)-dione
  参考文献：
  名称：

  Lead discovery of quinoxalinediones as an inhibitor of dipeptidyl peptidase-IV (DPP-IV) by high-throughput screening

  摘要：

  N-Ureido-quinoxalinedione derivatives have been discovered as leads for a novel series of dipeptidyl peptidase-IV (DPP-IV) inhibitors through high-throughput screening of our chemical library. A brief structure-activity relationship of the compounds was investigated. Among them, entry 5 showed the most potent inhibitory activity. The nitro group in quinoxaline moiety and the aromatic sulfonyl substituted ureido functional group seem to be important to increase the potency dramatically. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.02.065

文献信息

• Quinoxaline-2,3-dione compounds and their preparation and use
  申请人：Novo Nordisk A/S

  公开号：US05166155A1

  公开（公告）日：1992-11-24

  1-carboxyalkylquinoxaline-2,3(1H,4H)-dione compounds or tautomeric forms thereof of the formula ##STR1## wherein R represents hydrogen, C.sub.1-6 -alkyl, including branched chains, or aralkyl and n represents the number from 0 to 5; R.sup.4 represents hydrogen or hydroxy; R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently represent hydrogen, nitro, halogen, alkoxy, aryloxy, aralkoxy, C.sub.1-6 -alkyl including branched chains, or aryl; R.sup.9 represents hydrogen, lower alkyl, or aryl; R.sup.10 represents hydrogen, or alkyl. The compounds are useful in the treatment of neurological and psychiatric diseases.

  1-羧基烷基喹喔啉-2,3(1H,4H)-二酮化合物或其互变异构体，其化学式为##STR1##其中，R表示氢、C.sub.1-6-烷基（包括支链）或芳基烷基，n表示0到5的数字；R.sup.4表示氢或羟基；R.sup.5、R.sup.6、R.sup.7和R.sup.8独立地表示氢、硝基、卤素、烷氧基、芳氧基、芳基烷氧基、C.sub.1-6-烷基（包括支链）或芳基；R.sup.9表示氢、低碳基或芳基；R.sup.10表示氢或烷基。这些化合物可用于治疗神经和精神疾病。
• QUINOXALINE COMPOUNDS AND THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP0520024B1

  公开（公告）日：1996-06-19
• US5166155A
  申请人：——

  公开号：US5166155A

  公开（公告）日：1992-11-24
• Lead discovery of quinoxalinediones as an inhibitor of dipeptidyl peptidase-IV (DPP-IV) by high-throughput screening
  作者：Hyae-Gyeong Cheon、Chul-Min Lee、Beom-Tae Kim、Ki-Jun Hwang

  DOI：10.1016/j.bmcl.2004.02.065

  日期：2004.5

  N-Ureido-quinoxalinedione derivatives have been discovered as leads for a novel series of dipeptidyl peptidase-IV (DPP-IV) inhibitors through high-throughput screening of our chemical library. A brief structure-activity relationship of the compounds was investigated. Among them, entry 5 showed the most potent inhibitory activity. The nitro group in quinoxaline moiety and the aromatic sulfonyl substituted ureido functional group seem to be important to increase the potency dramatically. (C) 2004 Published by Elsevier Ltd.