4-carboxymethyl-1,4-dihydroquinoxaline-2,3-dione | 80310-03-8

• 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: 4-carboxymethyl-1,4-dihydroquinoxaline-2,3-dione
• 英文别名: 2-(2,3-dioxo-3,4-dihydroquinoxalin-1(2H)-yl)acetic acid；2,3-diketoquinoxaline-1-acetic acid；1-carboxymethylquinoxaline-2,3(1H,4H)-dione；2-(2,3-Dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)acetic acid；2-(2,3-dioxo-4H-quinoxalin-1-yl)acetic acid
• CAS: 80310-03-8
• 化学式: C₁₀H₈N₂O₄
• mdl: MFCD11858055
• 分子量: 220.185
• InChiKey: QBBQRMYAQGDFQB-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: ethanol (64-17-5))
• 密度：
  1.482±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 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：

  4-carboxymethyl-1,4-dihydroquinoxaline-2,3-dione 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2-oxo-3-{4-[(thiophen-2-ylmethyl)-carbamoyl]-phenylamino}-2H-quinoxalin-1-yl)-acetic acid trifluoroacetate salt
  参考文献：
  名称：

  Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors

  摘要：

  A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound I was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.021
• 作为产物：
  描述：

  (3-氧代-3,4-二氢-2H-喹噁啉-1-基)-乙酸 在 sodium hydroxide 、 potassium permanganate 作用下， 以 aq. NaOH 、 水 为溶剂， 以9.200 g (56%, pure by <SP>1</SP> H NMR)的产率得到4-carboxymethyl-1,4-dihydroquinoxaline-2,3-dione
  参考文献：
  名称：

  Glycine receptor antagonists and the use thereof

  摘要：

  治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术相关的神经元损失的方法，以及治疗包括阿尔茨海默病、肌萎缩侧索硬化、亨廷顿病和唐氏综合症在内的神经退行性疾病，治疗或预防兴奋性氨基酸过度活跃的副作用，以及治疗焦虑、慢性疼痛、癫痫、诱导麻醉和治疗精神病的方法，通过向需要此类治疗的动物施用一种对甘氨酸结合位点具有高亲和力、无PCP副作用且能穿过动物血脑屏障的化合物来进行披露。还披露了新型的1,4-二氢喹诺酮-2,3-二酮，及其药物组合物。还披露了1,4-二氢喹诺酮-2,3-二酮的高度可溶性铵盐。

  公开号：

  US05514680A1

文献信息

• DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS
  申请人：Chiesi Farmaceutici S.p.A.

  公开号：US20130102576A1

  公开（公告）日：2013-04-25

  Compounds, pyridine N-oxides, and pharmaceutically acceptable salts of formula (I) are useful as inhibitors of the phosphodiesterase 4 (PDE4) enzyme and for preventing and/or treating diseases of the respiratory tract characterized by airway obstruction, such as asthma or COPD.

  化合物，吡啶N-氧化物和具有以下结构的药学上可接受的盐（I）的盐对于抑制磷酸二酯酶4（PDE4）酶并预防和/或治疗呼吸道疾病，其特征是气道阻塞，如哮喘或COPD，是有用的。
• 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-羧基烷基喹啉并[2,3-]吡咯烷-2,3-二酮化合物或其互变异构体，其化学式为##STR1## 其中R代表氢，C.sub.1-6-烷基，包括支链，或芳基烷基，n代表0到5的数字；R.sup.4代表氢或羟基；R.sup.5，R.sup.6，R.sup.7和R.sup.8独立地代表氢，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代表氢，低烷基或芳基；R.sup.10代表氢或烷基。这些化合物在神经和精神疾病的治疗中有用。
• Cycloalkyl or benzyl-6-substituted-quinoxalinediones
  申请人：A/S Ferrosan

  公开号：US04948794A1

  公开（公告）日：1990-08-14

  Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.1 is C.sub.1-12 -alkyl, which may optionally be substituted by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C.sub.3-8 -cycloalkyl, aryl, aralkyl; and wherein R.sup.6 is, hydrogen, halogen, CN, CF.sub.3, NO.sub.2, or OR', wherein R' is C.sub.1-4 -alkyl and R.sup.5, R.sup.7 and R.sup.8 is hydrogen, provided R.sup.6 is not CF.sub.3, OCH.sub.3, NO.sub.2, C.sup.1 or Br when R.sup.1 is CH.sub.3 ; or R.sup.6 and R.sup.7 independently are NO.sub.2, halogen, CN, CF.sub.3, or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.8 are each hydrogen; or R.sup.5 and R.sup.6 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.7 and R.sup.8 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 -alkyl; or R.sup.7 and R.sup.8 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.6 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 -alkyl. The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use. The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters, particularly the quisqualate receptors, and especially as neuroleptics.

  具有以下式子的杂环二羟基喹啉化合物：##STR1##其中，R1为C1-12烷基，可以选择性地被羟基，甲酰基，羧基，羧酸酯，酰胺或胺取代，C3-8环烷基，芳基，芳基烷基；R6为氢，卤素，CN，CF3，NO2或OR'，其中R'为C1-4烷基，R5，R7和R8为氢，但当R1为CH3时，R6不为CF3，OCH3，NO2，C1或Br；或R6和R7独立地为NO2，卤素，CN，CF3或OR'，其中R'为C1-4烷基，R5和R8各为氢；或R5和R6共同形成进一步融合的芳香环，该环可以用卤素，NO2，CN，CF3或OR'取代，其中R'为C1-4烷基，R7和R8独立地为氢，卤素，CN，CF3，NO2或OR'，其中R'为C1-4烷基；或R7和R8共同形成进一步融合的芳香环，该环可以用卤素，NO2，CN，CF3或OR'取代，其中R'为C1-4烷基，R5和R6独立地为氢，卤素，CN，CF3，NO2或OR'，其中R'为C1-4烷基。本发明还涉及制备这些化合物的方法，其药物组成物和用途。这些化合物在治疗兴奋性神经递质引起的症状方面有用，特别是在治疗神经症方面有用。
• Benzo[f]quinoxaline-2,3(1H,4H)-diones
  申请人：Novo Nordisk A/S

  公开号：US05026704A1

  公开（公告）日：1991-06-25

  Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.1 is C.sub.1-12 -alkyl, which may optionally be substututed by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C.sub.3-8 -cycloalkyl, aryl, aralkyl; and wherein R.sup.6 is, hydrogen, halogen, CN, CF.sub.3, NO.sub.2, or OR', wherein R' is C.sub.1-4 -alkyl and R.sup.5, R.sup.7 and R.sup.8 is hydrogen, provided R.sup.6 is not CF.sub.3, OCH.sub.3, NO.sub.2, Cl or Br when R.sup.1 is CH.sub.3 ; or R.sup.6 and R.sup.7 independently are NO.sub.2, halogen, CN, CF.sub.3, or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.8 are each hydrogen; or R.sup.5 and R.sup.6 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.7 and R.sup.8 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 - alkyl; or R.sup.7 and R.sup.8 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.6 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 -alkyl. The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use. The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters, particularly the quisqualate receptors, and especially as neuroleptics.

  具有以下式子的杂环二羟基喹喔啉化合物：##STR1## 其中R.sup.1是C.sub.1-12烷基，可以选择被羟基，甲酰基，羧基，羧酸酯，酰胺或胺取代，C.sub.3-8环烷基，芳基，芳基烷基；R.sup.6是氢，卤素，CN，CF.sub.3，NO.sub.2或OR'，其中R'是C.sub.1-4烷基，R.sup.5，R.sup.7和R.sup.8是氢，只要当R.sup.1是CH.sub.3时，R.sup.6不是CF.sub.3，OCH.sub.3，NO.sub.2，Cl或Br；或者R.sup.6和R.sup.7分别是NO.sub.2，卤素，CN，CF.sub.3或OR'，其中R'是C.sub.1-4烷基，而R.sup.5和R.sup.8是氢；或者R.sup.5和R.sup.6一起形成另一个进一步融合的芳香环，其中可以用卤素，NO.sub.2，CN，CF.sub.3或OR'取代，其中R'是C.sub.1-4烷基，而R.sup.7和R.sup.8分别是氢，卤素，CN，CF.sub.3，NO.sub.2或OR'，其中R'是C.sub.1-4烷基；或者R.sup.7和R.sup.8一起形成另一个进一步融合的芳香环，其中可以用卤素，NO.sub.2，CN，CF.sub.3或OR'取代，其中R'是C.sub.1-4烷基，而R.sup.5和R.sup.6分别是氢，卤素，CN，CF.sub.3，NO.sub.2或OR'，其中R'是C.sub.1-4烷基。本发明还涉及制备这些化合物的方法，其制药组合物以及它们的用途。这些化合物在治疗兴奋性神经递质引起的症状方面是有用的，特别是在治疗神经精神病方面。
• Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
  申请人：Chiesi Farmaceutici S.p.A.

  公开号：US09024027B2

  公开（公告）日：2015-05-05

  Compounds, pyridine N-oxides, and pharmaceutically acceptable salts of formula (I) are useful as inhibitors of the phosphodiesterase 4 (PDE4) enzyme and for preventing and/or treating diseases of the respiratory tract characterized by airway obstruction, such as asthma or COPD.

  公式（I）的化合物，吡啶N-氧化物和药学上可接受的盐，可用作磷酸二酯酶4（PDE4）酶的抑制剂，并用于预防和/或治疗呼吸道疾病，其特征为气道阻塞，如哮喘或COPD。