2,3-dichloro-5-methylquinoxaline | 82463-30-7

• 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: 2,3-dichloro-5-methylquinoxaline
• CAS: 82463-30-7
• 化学式: C₉H₆Cl₂N₂
• 分子量: 213.066
• InChiKey: APGYEHZLFDBECC-UHFFFAOYSA-N

物化性质

• 沸点：
  289.1±35.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2,3-dichloro-5-methylquinoxaline 在 吡啶 、 氨 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 ethyl N-(3-methoxy-5-methylquinoxalin-2-yl)carbamate
  参考文献：
  名称：

  Synthesis, anticancer activity and pharmacokinetic analysis of 1-[(substituted 2-alkoxyquinoxalin-3-yl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives

  摘要：

  Based on the anticancer activity of novel quinoxalinyl-piperazine compounds, 1-[(5 or 6-substituted alkoxyquinoxalinyl) aminocarbonyl]-4-(hetero) arylpiperazine derivatives published in Bioorg. Med. Chem. 2010, 18, 7966, we further explored the synthesis of 7 or 8-substituted quinoxalinyl piperazine derivatives. From in vitro studies of the newly synthesized compounds using human cancer cell lines, we identified some of the 8-substituted compounds, for example 6p, 6q and 6r, which inhibited the proliferation of various human cancer cells at nanomolar concentrations. Compound 6r, in particular, showed the lowest IC50 values, ranging from 6.1 to 17 nM, in inhibition of the growth of cancer cells, which is better than compound 6k (compound 25 in the reference cited above). In order to select and develop a leading compound among the quinoxaline compounds with substitutions on positions 5, 6, 7 or 8, the compounds comparable to compound 6k in in vitro cancer cell growth inhibition were chosen and their pharmacokinetic properties were evaluated in rats. In these studies, compound 6k showed the highest oral bioavailability of 83.4%, and compounds 6j and 6q followed, with 77.8% and 57.6%, respectively. From the results of in vitro growth inhibitory activities and the pharmacokinetic study, compound 6k is suggested for further development as an orally deliverable anticancer drug. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.026
• 作为产物：
  描述：

  2,3-二氨基甲苯 在 盐酸 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,3-dichloro-5-methylquinoxaline
  参考文献：
  名称：

  作为潜在α-淀粉酶和α-葡萄糖苷酶抑制剂的新型苯基异恶唑喹喔啉-2-胺杂化物的合成、生物活性和评估分子对接动力学研究

  摘要：

  成功合成了新的苯基异恶唑喹喔啉-2-胺杂化物5a-i ，产率为 53-85%，并用各种光谱方法进行了表征。合成的杂交体进行了体外α-淀粉酶和α-葡萄糖苷酶抑制测定，以阿卡波糖作为阳性对照。通过生物学研究，化合物5h显示出最高的 α-淀粉酶抑制活性，IC 50 = 16.4 ± 0.1 μM，而化合物5a–c 、 5e和5h显示出作为 α-葡萄糖苷酶抑制剂的巨大潜力，其中5c最为有效（IC 50 = 15.2 ± 0.3 μM）。在这些化合物中， 5h显示出作为 α-淀粉酶 (IC 50 = 16.4 ± 0.1 μM) 和 α-葡萄糖苷酶 (IC 50 = 31.6 ± 0.4 μM) 双重抑制剂的潜力。通过分子对接研究，支持了所选化合物的抑制潜力。化合物5h表现出与α-淀粉酶活性位点的重要相互作用，并表现出最高结合能-8.9±0.10 kcal mol -1 ，而化合物5c通过与α-淀粉

  DOI：

  10.1039/d3ra08642a

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。
• [EN] FUSED TRICYCLIC COMPOUNDS WITH ADENOSINE A2a RECEPTOR ANTAGONIST ACTIVITY<br/>[FR] COMPOSÉS TRICYCLIQUES CONDENSÉS POSSÉDANT UNE ACTIVITÉ ANTAGONISTE DES RÉCEPTEURS A2A DE L'ADÉNOSINE
  申请人：SCHERING CORP

  公开号：WO2011060207A1

  公开（公告）日：2011-05-19

  The present invention relates to certain certain fused tricyclic heteroaryl rings compounds of the Formula (I) (also referred to herein as the "Fused Tricyclic Compounds"), wherein M, Q, U, W, X, Y, Z, R1, R2, and R3, and rings C and D are as herein described. The present invention also provides compositions comprising at least one Fused Tricyclic Compound, and use of such compounds in the treatment of central nervous system diseases or disorders such as Parkinson's disease.

  本发明涉及公式(I)中的某些融合三环杂环烷基环化合物（在此处也称为“融合三环化合物”），其中M、Q、U、W、X、Y、Z、R1、R2和R3以及环C和环D如所述。本发明还提供包含至少一种融合三环化合物的组合物，并利用这些化合物治疗中枢神经系统疾病或障碍，如帕金森病。