5-methylquinoxaline-2,3(1H,4H)-dione | 61875-33-0

• 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: 5-methylquinoxaline-2,3(1H,4H)-dione
• 英文别名: 5-methyl-1,4-dihydroquinoxaline-2,3-dione；5-Methyl-1,4-dihydro-2,3-quinoxalinedione；5-methyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline
• CAS: 61875-33-0
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: WBILTKMXRWMTNP-UHFFFAOYSA-N

物化性质

• 熔点：
  325-327 °C
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methylquinoxaline-2,3(1H,4H)-dione 在 五氯化磷 作用下， 反应 2.0h， 生成 7-Chloro-5-methyl-1,4-dihydroquinoxalin-2,3-dione
  参考文献：
  名称：

  5-aminomethylquinoxaline-2,3-diones. Part II: N-aryl derivatives as novel NMDA/glycine and AMPA antagonists

  摘要：

  Potent antagonists at the glycine-binding site of NMDA receptors, as well as dual antagonists acting also at AMPA receptors have been identified in a series of 5-arylaminomethylquinoxaline-2,3-diones. A study of the structure-activity relationship of these compounds is reported here. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10187-1
• 作为产物：
  描述：

  5-甲基喹喔啉 在 水 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以90%的产率得到5-methylquinoxaline-2,3(1H,4H)-dione
  参考文献：
  名称：

  使用超价λ为氧化喹喔啉，Tetraazaphenanthrene和六氮杂部分的直接方法3种-Iodinane化合物

  摘要：

  各种含贫电子的喹喔啉核心化合物，例如喹喔啉，1,4,5,8-四氮杂菲和1,4,5,8,9,12-六氮杂苯并菲的有效氧化反应，使用[双（三氟乙酰氧基）碘]苯的报道。使用乙腈/水溶剂混合物，可以在室温下将这些化合物以高收率或高收率转化为相应的喹喔啉二酮。这种空前的反应应能够合成可用于多个化学领域的多种化合物。

  DOI：

  10.1021/jo401872e

文献信息

• [EN] HETEROCYCLYL COMPOUNDS FOR THE TREATMENT OF AUTOIMMUNE DISEASE<br/>[FR] COMPOSÉS HÉTÉROCYCLYLES POUR LE TRAITEMENT D'UNE MALADIE AUTO-IMMUNE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2020064792A1

  公开（公告）日：2020-04-02

  The present invention relates to compounds of formula (I), wherein R1 to R3, A and Q are as described herein, and their pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

  本发明涉及式(I)的化合物，其中R1至R3，A和Q如本文所述，以及其药学上可接受的盐、对映体或二对映体，以及包括这些化合物的组合物和使用这些化合物的方法。
• KYNURENINE PRODUCTION INHIBITOR
  申请人：Amishiro Nobuyoshi

  公开号：US20110237584A1

  公开（公告）日：2011-09-29

  Provided is a kynurenine production inhibitor comprising a nitrogen-containing heterocyclic compound represented by formula (I): (wherein R 50 and R 51 may be the same or different and each represent a hydrogen atom or the like, G 1 and G 2 may be the same or different and each represent a nitrogen atom or the like, X represents formula (III): (wherein m 1 and m 2 may be the same or different and each represent an integer of 0 or 1, Y represents an oxygen atom or the like, and R 6 and R 7 may be the same or different and each represent a hydrogen atom or the like), R 1 represents optionally substituted lower alkyl or the like, R 2 represents a hydrogen atom or the like, and R 3 represents optionally substituted lower alkyl or the like), and the like.

  提供的是一种色氨酸代谢抑制剂，包括由式(I)表示的含氮杂环化合物：（其中R50和R51可以相同也可以不同，每个代表氢原子或类似物，G1和G2可以相同也可以不同，每个代表氮原子或类似物，X表示式(III)：（其中m1和m2可以相同也可以不同，每个代表0或1的整数，Y表示氧原子或类似物，R6和R7可以相同也可以不同，每个代表氢原子或类似物），R1表示可选择地取代的低碳烷基或类似物，R2表示氢原子或类似物，R3表示可选择地取代的低碳烷基或类似物），等等。
• [EN] NOVEL HETEROARYL HETEROCYCLYL COMPOUNDS FOR THE TREATMENT OF AUTOIMMUNE DISEASE<br/>[FR] NOUVEAUX COMPOSÉS HÉTÉROARLYLE HÉTÉROCYCLYLE POUR LE TRAITEMENT D'UNE MALADIE AUTO-IMMUNE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2019238616A1

  公开（公告）日：2019-12-19

  The present invention relates to compounds of formula (I), ab (I), wherein R1 to R3 and L are as described herein, and their pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

  本发明涉及式(I)的化合物，其中R1至R3和L如本文所述，以及其药用可接受的盐、对映体或二对映体，以及包括这些化合物的组合物和使用这些化合物的方法。
• A One-pot Facile Synthesis of 2,3-Dihydroxyquinoxaline and 2,3-Dichloroquinoxaline Derivatives Using Silica Gel as an Efficient Catalyst
  作者：Pei-Ming Zhang、Yao-Wei Li、Jing Zhou、Lin-Ling Gan、Yong-Jie Chen、Zong-Jie Gan、Yu Yu

  DOI：10.1002/jhet.3224

  日期：2018.7

  An efficient one‐pot reaction has been developed for the synthesis of 2,3‐dichloroquinoxaline derivatives 3a–n. The reaction was performed in two steps via a silica gel catalyzed tandem process from o‐phenylenediamine and oxalic acid, followed by addition of phosphorus oxychloride (POCl3). A variety of 2,3‐dichloroquinoxalines have been obtained in good to excellent overall yields. Eight known compounds

  已经开发出一种有效的一锅反应，用于合成2,3-二氯喹喔啉衍生物3a - n。该反应通过邻苯二胺和草酸的硅胶催化串联过程分两步进行，然后加入三氯氧化磷（POCl 3）。已获得各种2,3-二氯喹喔啉，总收率良好至极佳。通过IR，1 H-NMR和质谱对八种已知的化合物3a - 3h进行了表征。没有光谱数据的化合物3i - 3n的特征在于IR，1 H-NMR，13C-NMR和质谱。
• 2,3-dioxo-1,2,3,4-tetrahydro-quinoxalinyl derivatives
  申请人：Novartis AG

  公开号：US06080743A1

  公开（公告）日：2000-06-27

  2,3-Dioxo-1,2,3,4-tetrahydro-quinoxalinyl derivatives of formula (I), ##STR1## wherein one of the radicals R.sub.1, and R.sub.2 is a group R.sub.5 and the other is a group of formula --CH(R.sub.6)--alk--R.sub.7 (Ia), --alk--CH(R.sub.6 -R.sub.7 (Ib), --alk--N(R.sub.8)--X--R.sub.7 (Ic), --alk--N.sup.+ (R.sub.8)(R.sup.9)--X--R.sub.7 A.sup.- (Id), --alk--O--X--R.sub.7 (Ie) or --alk--S--X--R.sub.7 (If), R.sub.3, R.sub.4 and R.sub.5 are each independently of the others hydrogen, lower alkyl, halogen, trifluoromethyl, cyano or nitro, R.sub.6 is unsubstituted or lower alkylated and/or lower alkanoylated amino, R.sub.7 is hydrogen; an aliphatic, cycloaliphatic or heterocycloaliphatic radical; cyano; acyl derived from carbonic acid or from a semiester or semiamide of carbonic acid, from sulfuric acid or from an aliphatic or aromatic sulfonic acid or from phosphoric acid or from a phosphonic acid ester; amino that is unsubtituted or aliphatically or araliphatically substituted and/or substituted by aliphatic, araliphatic or aromatic acyl; or an aromatic or heteroaromatic radical, R.sub.8 is hydrogen; an aliphatic or araliphatic radical; or acyl derived from an aliphatic or araliphatic carboxylic acid or from an aliphatic or araliphatic semiester of carbonic acid, or R.sub.7 and R.sub.8, together with X and the nitrogen atom bonding R.sub.8 and X, form an unsubstitued or substituted mono- or di-azaxycloalkyl, azoxacycloalkyl, azathiacycloalkyl or optionally oxidised thiacycloalkyl radical bonded via a nitrogen atom, or an unsubstituted or substituted, optionally partially hxdrogenated aryl or heteroaryl radical, R.sub.9 is an aliphatic or araliphatic radical, or R.sub.7, R.sub.8 and R.sub.9 together with X and the nitrogen atom bonding R.sub.8, R.sub.9 and X, form an unsubstituted or substituted quaternary heteroaryl radical bonded via the quaternary nitrogen atom, with A.sup.- being the anion of a protonic acid, alk is lower alkylene, and X (unless, together with R.sub.7 and R.sub.8 and the nitrogen atom bonding R.sub.8 and X or together with the nitrogen atom bonding R.sub.8, R.sub.9 and X, it forms part of one of the mentioned ring systems) is a divalent aliphatic, cycloaliphatic or araliphatic radical or a direct bond, and the pharmaceutically acceptable salts thereof can be used in the preparation of a medicament for the treatment of pathological conditions that are responsive to blocking of AMPA, kainate and/or glycine binding sites of the NMDA receptor.

  公式(I)的2,3-二氧代-1,2,3,4-四氢喹啉基衍生物，其中R.sub.1和R.sub.2中的一个是R.sub.5基团，另一个是--CH(R.sub.6)--alk--R.sub.7 (Ia)、--alk--CH(R.sub.6)--R.sub.7 (Ib)、--alk--N(R.sub.8)--X--R.sub.7 (Ic)、--alk--N.sup.+ (R.sub.8)(R.sup.9)--X--R.sub.7 A.sup.- (Id)、--alk--O--X--R.sub.7 (Ie)或--alk--S--X--R.sub.7 (If)的公式基团；R.sub.3、R.sub.4和R.sub.5各自独立地是氢、低碳基、卤素、三氟甲基、氰基或硝基；R.sub.6是未取代或低碳基化和/或低脂肪酰化的氨基；R.sub.7是氢；一种脂肪、环脂或杂环脂基；氰基；从碳酸或碳酸半酯或半酰胺、硫酸或脂肪或芳香磺酸、磷酸或膦酸酯衍生的酰基；未取代或烷基或芳基取代和/或烷基、芳基或芳香酰基取代的氨基；或芳香或杂环芳基，R.sub.8是氢；一种脂肪或芳基基团；或从脂肪或芳香羧酸或从碳酸的脂肪或芳香半酯衍生的酰基，或R.sub.7和R.sub.8连同X和与R.sub.8和X连接的氮原子形成未取代或取代的单环或二环氮杂环脂、氧杂环脂、硫杂环脂或可选择氧化的硫杂环脂基，通过氮原子连接，或未取代或取代的、可选择部分氢化的芳基或杂芳基基团，R.sub.9是一种脂肪或芳基基团，或R.sub.7、R.sub.8和R.sub.9连同X和连接R.sub.8、R.sub.9和X的氮原子形成通过季铵氮原子连接的未取代或取代的杂芳基基团，A.sup.-是质子酸的阴离子，alk是低碳烷基，X（除非与R.sub.7和R.sub.8以及连接R.sub.8和X的氮原子或与连接R.sub.8、R.sub.9和X的氮原子形成所述环系统之一的一部分）是二价的脂肪、环脂或芳基基团或直接键，其药学上可接受的盐可用于制备用于治疗对AMPA、kainate和/或甘氨酸-NMDA受体结合位点阻塞敏感的病理条件的药物。