2-amino-3-(thiazol-2-yl)-6,7-dichloroquinoxaline | 232604-25-0

• 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: 2-amino-3-(thiazol-2-yl)-6,7-dichloroquinoxaline
• 英文别名: 6,7-Dichloro-3-(1,3-thiazol-2-yl)quinoxalin-2-amine
• CAS: 232604-25-0
• 化学式: C₁₁H₆Cl₂N₄S
• 分子量: 297.167
• InChiKey: HGBGLAJAGHRZCB-UHFFFAOYSA-N

物化性质

• 沸点：
  501.5±60.0 °C(Predicted)
• 密度：
  1.613±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-二甲氨基氯丙烷盐酸盐 、 2-amino-3-(thiazol-2-yl)-6,7-dichloroquinoxaline 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以60%的产率得到N'-(6,7-Dichloro-3-thiazol-2-yl-quinoxalin-2-yl)-N,N-dimethyl-propane-1,3-diamine
  参考文献：
  名称：

  Synthesis and structure–Activity relationship of 2-amino-3-heteroaryl-quinoxalines as non-peptide, small-Molecule antagonists for interleukin-8 receptor

  摘要：

  Interleukin-8 modulation is implicated in many inflammatory and cancer diseases. Starting from a mass-screening hit, the synthesis and structure-activity relationship of 2-amino-3-heteroarylquinoxalines as non-peptide, small molecule interleukine-8 receptor antagonists have been developed. The optimized derivatives, PD 0210293 (13y) and PD 0220245 (13r), show inhibition of both IL-8 receptor binding and IL-8-mediated neutrophil chemotaxis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00399-7
• 作为产物：
  描述：

  2,3-二羟基-6,7-二氯喹喔啉 在 bis-triphenylphosphine-palladium(II) chloride ammonium hydroxide 、 copper(l) iodide 、 五溴化磷 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 2-amino-3-(thiazol-2-yl)-6,7-dichloroquinoxaline
  参考文献：
  名称：

  Synthesis and structure–Activity relationship of 2-amino-3-heteroaryl-quinoxalines as non-peptide, small-Molecule antagonists for interleukin-8 receptor

  摘要：

  Interleukin-8 modulation is implicated in many inflammatory and cancer diseases. Starting from a mass-screening hit, the synthesis and structure-activity relationship of 2-amino-3-heteroarylquinoxalines as non-peptide, small molecule interleukine-8 receptor antagonists have been developed. The optimized derivatives, PD 0210293 (13y) and PD 0220245 (13r), show inhibition of both IL-8 receptor binding and IL-8-mediated neutrophil chemotaxis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00399-7

文献信息

• Synthesis of 3-aryl and 3-heterocyclic quinoxalin-2-ylamines via Pd-catalyzed cross-coupling reactions
  作者：Jie Jack Li、Wen Song Yue

  DOI：10.1016/s0040-4039(99)00822-9

  日期：1999.6
• US6548499B1
  申请人：——

  公开号：US6548499B1

  公开（公告）日：2003-04-15
• [EN] SUBSTITUTED QUINOXALINE DERIVATIVES AS INTERLEUKIN-8 RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE QUINOXALINE SUBSTITUES UTILISES COMME ANTAGONISTES DU RECEPTEUR DE L'INTERLEUKINE-8
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1999042463A1

  公开（公告）日：1999-08-26

  (EN) Quinoxaline compounds are described as well as methods for the preparation and pharmaceutical compositions of same, which are useful as interleukin-8 (IL-8) receptor antagonists and can be used in the treatment of a chemokine-mediated disease wherein the chemokine binds to an IL-8a (CXCR1) or b (CXCR2) receptor such as a chemokine-mediated disease selected from psoriasis, or atopic dermatitis, disease associated with pathological angiogenesis (i.e. cancer), asthma, chronic obstructive pulmonary disease, adult respiratory distress syndrome, arthritis, inflammatory bowel disease, Crohn's disease, ulcerative colitis, gastric ulcer, septic shock, endotoxic shock, gram-negative sepsis, toxic shock syndrome, stroke, cardiac and renal reperfusion injury, glomerulo-nephritis, or thrombosis, Alzheimer's disease, graft versus host reaction, allograft rejections, or allergic diseases.(FR) L'invention porte sur des composés de quinoxaline, ainsi que sur leurs procédés de préparation et leurs compositions pharmaceutiques. Ces composés sont utiles comme antagonistes du récepteur de l'interleukine-8 (IL-8) et peuvent être utilisés dans le traitement d'une maladie induite par la chémokine, la chémokine se fixant à un récepteur d'IL-8a (CXCR1) ou b (CXCR2), telle que le psoriasis ou la dermatite atopique, une maladie associée à l'angiogenèse pathologique (c.-à-d. le cancer), l'asthme, la maladie pulmonaire obstructive chronique, le syndrome de la détresse respiratoire de l'adulte, l'arthrite, la maladie intestinale inflammatoire, la maladie de Crohn, la resto-colite hémorragique, l'ulcère gastrique, le choc septique, le choc endotoxinique, la septicémie à germes Gram négatif, le syndrome de choc toxique, l'ictus, les lésions cardiaques et rénales de perfusion répétée, la glomérulonéphrite ou la thrombose, la maladie d'Alzheimer, la réaction du greffon contre l'hôte, les rejets de greffe allogénique ou les maladies allergiques.
• Synthesis and structure–Activity relationship of 2-amino-3-heteroaryl-quinoxalines as non-peptide, small-Molecule antagonists for interleukin-8 receptor
  作者：Jie Jack Li、Kenneth G Carson、Bharat K Trivedi、Wen Song Yue、Qing Ye、Roberta A Glynn、Steven R Miller、David T Connor、Bruce D Roth、Jay R Luly、Joseph E Low、David J Heilig、Weixing Yang、Shixin Qin、Stephen Hunt

  DOI：10.1016/s0968-0896(03)00399-7

  日期：2003.8

  Interleukin-8 modulation is implicated in many inflammatory and cancer diseases. Starting from a mass-screening hit, the synthesis and structure-activity relationship of 2-amino-3-heteroarylquinoxalines as non-peptide, small molecule interleukine-8 receptor antagonists have been developed. The optimized derivatives, PD 0210293 (13y) and PD 0220245 (13r), show inhibition of both IL-8 receptor binding and IL-8-mediated neutrophil chemotaxis. (C) 2003 Elsevier Ltd. All rights reserved.