2,3-dimethyl-5-quinoxalinecarboxaldehyde | 317593-27-4

• 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-dimethyl-5-quinoxalinecarboxaldehyde
• 英文别名: 2,3-Dimethylquinoxaline-5-carbaldehyde
• CAS: 317593-27-4
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: ARZGTKCMSVJVHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-5-quinoxalinecarboxaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以85%的产率得到2-吡啶羧酸,5-(3,4-二氯苯基)-
  参考文献：
  名称：

  RESPIRATORY SYNCYTIAL VIRUS REPLICATION INHIBITORS

  摘要：

  公开号：

  EP1196410B1
• 作为产物：
  描述：

  (+/-)-1,2,3,4-tetrahydro-2,3-dimethyl-5-quinoxaline-methanol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到2,3-dimethyl-5-quinoxalinecarboxaldehyde
  参考文献：
  名称：

  RESPIRATORY SYNCYTIAL VIRUS REPLICATION INHIBITORS

  摘要：

  公开号：

  EP1196410B1

文献信息

• Respiratory syncytial virus replication inhibitors
  申请人：Janssens Eduard Frans

  公开号：US20060058309A1

  公开（公告）日：2006-03-16

  The present invention concerns compounds of formula (I), prodrugs, N-oxides, addition salts, quaternary amines, metal complexes and stereochemically isomeric forms thereof wherein -a 1 =a 2 -a 3 =a 4 - represents a radical of formula —CH═CH—CH═CH—; —N═CH—CH═CH—; —CH═N—CH═CH—; —CH═CH—N═CH—; CH═CH—CH═N—; wherein each hydrogen atom may optionally be substituted; Q is a radical of formulae (b-1), (b-2), (b-3), (b-4), (b-5), (b-6), (b-7) and (b-8), wherein Alk is C 1-6 alkanediyl; Y 1 is a bivalent radical of formula —NR 2 — or —CH(NR 2 R 4 ); X 1 is NR 4 , S, S(═O), S(═O) 2 , O, CH 2 , C(═O), CH(═CH 2 ), CH(OH), CH(CH 3 ), CH(OCH 3 ), CH(SCH 3 ), CH(NR 5a R 5b ), CH 2 —NR 4 or NR 4 —CH 2 ; X 2 is a direct bond, CH 2 , C(═O), NR 4 , C 1-4 alkyl-NR 4 , NR 4 —C 1-4 alkyl, t is 2 to 5; u is 1 to 5; v is 2 or 3; and whereby each hydrogen in Alk and in (b-3), (b-4), (b-5), (b-6), (b-7) and (b-8), may optionally be replaced by R 3 ; provided that when R 3 is hydroxy or C 1-6 alkyloxy, then R 3 cannot replace a hydrogen atom in the α position relative to a nitrogen atom; G is a direct bond or optionally substituted C 1-10 alkanediyl; R 1 is an optionally substituted bicyclic heterocycle; R 2 is hydrogen, formyl, C 1-6 alkylcarbonyl, Hetcarbonyl, pyrrolidinyl, piperidinyl, homopiperidinyl, C 3-7 cycloalkyl or C 1-10 alkyl substituted with N(R 6 ) 2 and optionally with another substituent; R 3 is hydrogen, hydroxy, C 1-6 alkyl, C 1-6 alkyloxy, arylC 1-6 alkyl or arylC 1-6 alkyloxy, R 4 is hydrogen, C 1-6 alkyl or arylC 1-6 alkyl; R 5a , R 5b , R 5c and R 5d are hydrogen or C 1-6 alkyl; or R 5a and R 5b , or R 5c and R 5d taken together from a bivalent radical of formula —(CH 2 ) S — wherein S is 4 or 5; R 6 is hydrogen, C 1-4 alkyl, formyl, hydroxyC 1-6 alkyl, C 1-6 alkylcarbonyl or C 1-6 alkyloxycarbonyl; aryl is optionally substituted phenyl; Het is pyridyl, pyrimidinyl, pyryzinyl, pyridazinyl; as respiratory syncytial virus replication inhibitors; their preparation, compositions containing them and their use as a medicine.

  本发明涉及公式（I）的化合物，前药，N-氧化物，加成盐，季铵盐，金属配合物和立体化学异构体，其中-a1 = a2-a3 = a4-表示公式—CH = CH-CH = CH-;—N = CH-CH = CH-;—CH = N-CH = CH-;—CH = CH-N = CH-; CH = CH-CH = N-;其中每个氢原子可以选择被取代；Q是公式（b-1），（b-2），（b-3），（b-4），（b-5），（b-6），（b-7）和（b-8）的基团，其中Alk是C1-6烷基二亚基；Y1是公式—NR2—或—CH（NR2R4）的双价基团；X1是NR4，S，S（═O），S（═O）2，O，CH2，C（═O），CH（═CH2），CH（OH），CH（CH3），CH（OCH3），CH（SCH3），CH（NR5aR5b），CH2—NR4或NR4—CH2；X2是直接键，CH2，C（═O），NR4，C1-4烷基-NR4，NR4—C1-4烷基，t为2至5；u为1至5；v为2或3；其中Alk和（b-3），（b-4），（b-5），（b-6），（b-7）和（b-8）中的每个氢可以选择被R3取代；但是当R3为羟基或C1-6烷氧基时，R3不能取代氮原子相对的α位置上的氢原子；G是直接键或可选择取代的C1-10烷基二亚基；R1是可选择取代的双环杂环；R2是氢，甲酰基，C1-6烷基羰基，Hetcarbonyl，吡咯烷基，哌啶基，同半哌啶基，C3-7环烷基或C1-10烷基，其被N（R6）2和可选择另一个取代基取代；R3是氢，羟基，C1-6烷基，C1-6烷氧基，芳基C1-6烷基或芳基C1-6烷氧基；R4是氢，C1-6烷基或芳基C1-6烷基；R5a，R5b，R5c和R5d是氢或C1-6烷基；或R5a和R5b，或R5c和R5d一起形成公式—（CH2）S—的双价基团，其中S为4或5；R6是氢，C1-4烷基，甲酰基，羟基C1-6烷基，C1-6烷基羰基或C1-6烷氧羰基；芳基是可选择取代的苯基；Het是吡啶基，嘧啶基，吡啶啉基，吡嗪啉基；作为呼吸道合胞病毒复制抑制剂；它们的制备，含有它们的组合物以及它们作为药物的用途。
• Discovery of Potent Pyrazoline‐Based Covalent SARS‐CoV‐2 Main Protease Inhibitors**
  作者：Patrick Moon、Charlotte M. Zammit、Qian Shao、Dustin Dovala、Lydia Boike、Nathaniel J. Henning、Mark Knapp、Jessica N. Spradlin、Carl C. Ward、Helene Wolleb、Daniel Fuller、Gabrielle Blake、Jason P. Murphy、Feng Wang、Yipin Lu、Stephanie A. Moquin、Laura Tandeske、Matthew J. Hesse、Jeffrey M. McKenna、John A. Tallarico、Markus Schirle、F. Dean Toste、Daniel K. Nomura

  DOI：10.1002/cbic.202300116

  日期：2023.6

  synthesis of di- and tri-substituted pyrazolines bearing either chloroacetamide or vinyl sulfonamide cysteine-reactive warheads, we have discovered nanomolar potency inhibitors against Mpro from not only SARS-CoV-2, but across many other coronaviruses.

  使用共价化学蛋白质组学策略、结构导向的药物化学以及带有氯乙酰胺或乙烯基磺酰胺半胱氨酸反应弹头的二取代和三取代吡唑啉的模块化合成，我们不仅从 SARS-CoV-2、但跨越许多其他冠状病毒。
• US7071192B1
  申请人：——

  公开号：US7071192B1

  公开（公告）日：2006-07-04
• US7407969B2
  申请人：——

  公开号：US7407969B2

  公开（公告）日：2008-08-05
• [EN] RESPIRATORY SYNCYTIAL VIRUS REPLICATION INHIBITORS<br/>[FR] INHIBITEURS DE RÉPLICATION DE VIRUS SYNCYTIAUX RESPIRATOIRES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2001000615A1

  公开（公告）日：2001-01-04

  The present invention concerns compounds of formula (I), prodrugs, N-oxides, addition salts, quaternary amines, metal complexes and stereochemically isomeric forms thereof wherein -a?1=a2-a3=a4¿- represents a radical of formula -CH=CH-CH=CH-; -N=CH-CH=CH-; -CH=N-CH=CH-; -CH=CH-N=CH-; -CH=CH-CH=N-; wherein each hydrogen atom may optionally be substituted; Q is a radical of formulae (b-1), (b-2), (b-3), (b-4), (b-5), (b-6), (b-7) and (b-8), wherein Alk is C¿1-6?alkanediyl; Y?1¿ is a bivalent radical of formula -NR2- or -CH(NR?2R4)-; X1 is NR4¿, S, S(=O), S(=O)¿2?, O, CH2, C(=O), CH(=CH2), CH(OH), CH(CH3), CH(OCH3), CH(SCH3), CH(NR?5aR5b), CH¿2-NR?4 or NR4-CH¿2; X2 is a direct bond, CH¿2?, C(=O), NR?4, C¿1-4alkyl-NR?4, NR4-C¿1-4alkyl, t is 2 to 5; u is 1 to 5; v is 2 or 3; and whereby each hydrogen in Alk and in (b-3), (b-4), (b-5), (b-6), (b-7) and (b-8), may optionally be replaced by R3; provided that when R3 is hydroxy or C¿1-6?alkyloxy, then R?3¿ cannot replace a hydrogen atom in the α position relative to a nitrogen atom; G is a direct bond or optionally substituted C¿1-10?alkanediyl; R?1¿ is an optionally substituted bicyclic heterocycle; R2 is hydrogen, formyl, C¿1-6?alkylcarbonyl, Hetcarbonyl, pyrrolidinyl, piperidinyl, homopiperidinyl, C3-7cycloalkyl or C1-10alkyl substituted with N(R?6)¿2 and optionally with another substituent; R3 is hydrogen, hydroxy, C¿1-6?alkyl, C1-6alkyloxy, arylC1-6alkyl or arylC1-6alkyloxy, R?4¿ is hydrogen, C¿1-6?alkyl or arylC1-6alkyl; R?5a, R5b, R5c and R5d¿ are hydrogen or C¿1-6?alkyl; or R?5a and R5b, or R5c and R5d¿ taken together from a bivalent radical of formula -(CH¿2?)s- wherein S is 4 or 5; R?6¿ is hydrogen, C¿1-4?alkyl, formyl, hydroxyC1-6alkyl, C1-6alkylcarbonyl or C1-6alkyloxycarbonyl; aryl is optionally substituted phenyl; Het is pyridyl, pyrimidinyl, pyryzinyl, pyridazinyl; as respiratory syncytial virus replication inhibitors; their preparation, compositions containing them and their use as a medicine.