1-cyclo-hexyl-6-nitroquinoxaline-2,3(1H,4H)-dione | 123855-70-9

• 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-cyclo-hexyl-6-nitroquinoxaline-2,3(1H,4H)-dione
• 英文别名: 1-cyclohexyl-6-nitroquinoxaline-2,3(1H,4H)-dione；4-cyclohexyl-7-nitro-1H-quinoxaline-2,3-dione
• CAS: 123855-70-9
• 化学式: C₁₄H₁₅N₃O₄
• 分子量: 289.291
• InChiKey: WDRTYCDZHXTCLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-cyclo-hexyl-6-nitroquinoxaline-2,3(1H,4H)-dione 在 palladium on activated charcoal 硫酸 、 氢气 、 potassium nitrate 作用下， 生成 7-amino-1-cyclohexyl-6-nitro-2,3(1H,4H)-quinoxalinedione
  参考文献：
  名称：

  Pyrrolylquinoxalinediones: A new class of AMPA receptor antagonists

  摘要：

  Pyrrolylquinoxalinediones were synthesized and their affinities for the AMPA receptor were determined. Most compounds showed moderate to good affinities. The acetic acid derivative 8b exhibited a K-i value of 70 nM and was equipotent to NBQX 1. Structure activity relationships are discussed. Selected compounds were tested for their potency to inhibit AMPA induced lethal convulsions in mice. In this in vivo model the compounds showed improved potency compared with NBQX. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00534-3
• 作为产物：
  描述：

  N-cyclohexyl-2,4-dinitroaniline 在 铁粉 、 溶剂黄146 作用下， 生成 1-cyclo-hexyl-6-nitroquinoxaline-2,3(1H,4H)-dione
  参考文献：
  名称：

  Pyrrolylquinoxalinediones: A new class of AMPA receptor antagonists

  摘要：

  Pyrrolylquinoxalinediones were synthesized and their affinities for the AMPA receptor were determined. Most compounds showed moderate to good affinities. The acetic acid derivative 8b exhibited a K-i value of 70 nM and was equipotent to NBQX 1. Structure activity relationships are discussed. Selected compounds were tested for their potency to inhibit AMPA induced lethal convulsions in mice. In this in vivo model the compounds showed improved potency compared with NBQX. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00534-3

文献信息

• 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。
• Quinoxaline compounds and their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0315959A2

  公开（公告）日：1989-05-17

  Heterocyclic dihydroxyquinoxaline compounds having the formula wherein R¹ is C₁₋₁₂-alkyl, which may obtionally be substituted by hydroxy, formyl, carboxy, carboxylic esters, amides or ami­nes, C₃₋₈-cycloalkyl, aryl, aralkyl; and wherein R⁶ is, hy­drogen, halogen, CN, CF₃, NO₂, or OR′, wherein R′ is C₁₋₄-­alkyl and R⁵, R⁷ and R⁸ is hydrogen, provided R⁶ is not CF₃, OCH₃, NO₂, CL or Br when R¹ is CH₃; or R⁶ and R⁷ independently are NO₂, halogen, CN, CF₃, or OR′, wherein R′ is C₁₋₄-alkyl, and R⁵ and R⁸ are each hydrogen; or R⁵ and R⁶ together form a further fused aromatic ring, which may be substituted with halogen, NO₂, CN, CF₃ or OR′, wherein R′ is C₁₋₄-alkyl, and R⁷ and R⁸ independently are hydrogen, halogen, CN, CF₃, NO₂ or OR′ wherein R′ is C₁₋₄-alkyl; or R⁷ and R⁸ together form a further fused aromatic ring, which may be substituted with halogen, NO₂, CN, CF₃ or OR′, wherein R′ is C₁₋₄-alkyl, and R⁵ and R⁶ independently are hydrogen, halogen, CN, CF₃, NO₂ or OR′, wherein R′ is C₁₋₄-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 其中 R¹ 是 C₁₋₁₂-烷基，可被羟基、甲酰基、羧基、羧酸酯、酰胺或胺、C₃₋₈-环烷基、芳基、芳烷基取代；其中 R⁶ 是氢、卤素、CN、CF₃、NO₂ 或 OR′，其中 R′ 是 C₁₋₄-烷基和 R⁵、R⁷ 和 R⁸ 是氢，条件是 R⁶ 不是 CF₃、OCH₃、NO₂、CL 或 Br（当 R¹ 是 CH₃ 时）；或 R⁶ 和 R⁷ 独立地为 NO₂、卤素、CN、CF₃ 或 OR′，其中 R′为 C₁₋₄-烷基，且 R⁵ 和 R⁸ 均为氢；或 R⁵ 和 R⁶ 共同形成另一个可被卤素、NO₂、CN、CF₃ 或 OR′取代的融合芳环、其中 R′为 C₁₄-烷基，且 R⁷ 和 R⁸ 独立地为氢、卤素、CN、CF₃、NO₂ 或 OR′，其中 R′为 C₁₄-烷基；或 R⁷ 和 R⁸ 共同形成另一个可被卤素、NO₂、CN、CF₃ 或 OR′取代的融合芳环、其中 R′为 C₁₋₄-烷基，且 R⁵ 和 R⁶ 独立地为氢、卤素、CN、CF₃、NO₂ 或 OR′，其中 R′为 C₁₋₄-烷基。 本发明还涉及化合物的制备方法、其药物组合物及其用途。 本发明的化合物可用于治疗兴奋性神经递质，特别是喹乙醇受体亢进引起的适应症，尤其可用作神经抑制剂。
• JPH01153680A
  申请人：——

  公开号：JPH01153680A

  公开（公告）日：1989-06-15
• PROBENECID FOR USE IN TREATING EPILEPTIC DISEASES, DISORDERS OR CONDITIONS
  申请人：PARIS SCIENCES ET LETTRES - QUARTIER LATIN

  公开号：US20200163916A1

  公开（公告）日：2020-05-28

  Probenecid or a pharmaceutical acceptable salt thereof for use in the treatment of a neurological disorder in a subject in need thereof, wherein administration of probenecid or a pharmaceutical acceptable salt thereof controls clinical or electrographic seizures in the subject. Preferably, the neurological disorder is an epileptic disease, disorder or condition.