3,7-dichloro-2-quinoxalinecarbonitrile 1,4-di-N-oxide | 171880-81-2

• 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: 3,7-dichloro-2-quinoxalinecarbonitrile 1,4-di-N-oxide
• 英文别名: 2,6-dichloro-3-cyano-quinoxaline 1,4-dioxide；3,7-Dichloro-4-oxido-1-oxoquinoxalin-1-ium-2-carbonitrile
• CAS: 171880-81-2
• 化学式: C₉H₃Cl₂N₃O₂
• 分子量: 256.048
• InChiKey: XHRHZGAJNMCBQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,7-dichloro-2-quinoxalinecarbonitrile 1,4-di-N-oxide 、 1-胡椒基哌嗪 在 potassium carbonate 、 2,7-dichloro-3-cyano-quinoxaline 1,4-dioxide 作用下， 以 氯仿 为溶剂， 反应 480.0h， 以16%的产率得到3-(4-Benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-7-chloro-1,4-dioxy-quinoxaline-2-carbonitrile
  参考文献：
  名称：

  New quinoxalinecarbonitrile 1,4-di-N-oxide derivatives as hypoxic-cytotoxic agents

  摘要：

  We report the synthesis and biological in vitro activities of 16 new 2-quinoxalinecarbonitrile 1,4-di-N-oxides. These compounds present new basic lateral chains (piperazines and anilines) in the 3 position as well as different substituents in the 6 and/or 7 positions of the quinoxaline ring. Among piperazine derivatives, 4b (a 7-chloro-3-(4-methylpiperaiin-1-yl) derivative) was the most potent (P = 0.5 x 10(-6) M). In general, aniline derivatives were more potent and selective than the former, compound 12b (with a 4-(methylphenyl)amino moiety in the 3 position and a chlorine atom in the 7 position) being the best one (P = 3 x 10-6 M and HCR > 16). (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00112-4
• 作为产物：
  描述：

  3-amino-7-chloro-2-quinoxalinecarbonitrile 1,4-di-N-oxide 在 亚硝酸特丁酯 、 copper dichloride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 3,7-dichloro-2-quinoxalinecarbonitrile 1,4-di-N-oxide
  参考文献：
  名称：

  Aldana, Ignacio; Ortega; Jaso, Pharmazie, 2003, vol. 58, # 1, p. 68 - 69

  摘要：

  DOI：
• 作为试剂：
  描述：

  2,7-dichloro-3-cyano-quinoxaline 1,4-dioxide 、 1-胡椒基哌嗪 在 potassium carbonate 、 3,7-dichloro-2-quinoxalinecarbonitrile 1,4-di-N-oxide 作用下， 以 氯仿 为溶剂， 反应 480.0h， 以1%的产率得到3-(4-benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-6-chloro-1,4-dioxy-quinoxaline-2-carbonitrile
  参考文献：
  名称：

  New quinoxalinecarbonitrile 1,4-di-N-oxide derivatives as hypoxic-cytotoxic agents

  摘要：

  We report the synthesis and biological in vitro activities of 16 new 2-quinoxalinecarbonitrile 1,4-di-N-oxides. These compounds present new basic lateral chains (piperazines and anilines) in the 3 position as well as different substituents in the 6 and/or 7 positions of the quinoxaline ring. Among piperazine derivatives, 4b (a 7-chloro-3-(4-methylpiperaiin-1-yl) derivative) was the most potent (P = 0.5 x 10(-6) M). In general, aniline derivatives were more potent and selective than the former, compound 12b (with a 4-(methylphenyl)amino moiety in the 3 position and a chlorine atom in the 7 position) being the best one (P = 3 x 10-6 M and HCR > 16). (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00112-4

文献信息

• Hypoxia-Selective Agents Derived from 2-Quinoxalinecarbonitrile 1,4-Di-N-oxides. 2
  作者：Antonio Monge、Francisco J. Martinez-Crespo、Adela Lopez de Cerain、Juan A. Palop、Susana Narro、Virginia Senador、Ana Marin、Yolanda Sainz、Mercedes Gonzalez

  DOI：10.1021/jm00022a014

  日期：1995.10

  different groups in position 3. Thus, the synthesis of some 3-NH-substituted derivatives (2a, 3a, 4a) starting from 3-amino-2-quinoxalinecarbonitrile 1,4-di-N-oxide (1a) is described. Reductive deamination of compounds 1a-k provides the 2-quinoxalinecarbonitriles 5a-k, which are more potent, while selectivity is maintained or increased in some derivatives. The compound 7-(4-nitrophenyl)-2-quinoxalinecarbonitrile

  缺氧细胞是抗肿瘤治疗的重要靶标，因为肿瘤通常以此类细胞为特征。几乎所有以实体块形式存在的肿瘤都含有低氧细胞，而正常细胞通常具有充足的氧气供应。因此，由于在低氧条件下的高活性，可以使抗肿瘤药对肿瘤具有选择性。这项工作的最初目的是确定位置3上不同基团的影响。因此，从3-氨基-2-喹喔啉甲腈1,4-开始合成一些3-NH取代的衍生物（2a，3a，4a）描述了二-N-氧化物（1a）。化合物1a-k的还原性脱氨基反应提供了更有效的2-喹喔啉腈5a-k，同时在某些衍生物中保持或提高了选择性。化合物7-（4-硝基苯基）-2-喹喔啉甲腈1,4-二-N-氧化物（5k）比替拉帕明（3-氨基-1,2,4-苯并三嗪1,4-二-N-氧化物），已用作标准。在V79细胞中，三种衍生物（5g，i，k）的缺氧细胞毒性比（HCR）>或= 200，优于替拉帕明（HCR = 75）。用氯取代3-氨基可得到有效的但非选择性的3-氯衍
• Ortega; Montoya; Jaso, Pharmazie, 2001, vol. 56, # 3, p. 205 - 207
  作者：Ortega、Montoya、Jaso、Zarranz、Tirapu、Aldana、Monge

  DOI：——

  日期：——
• Ortega; Sainz; Montoya, Pharmazie, 1999, vol. 54, # 1, p. 24 - 26
  作者：Ortega、Sainz、Montoya、Lopez De Cerain、Monge

  DOI：——

  日期：——
• New quinoxalinecarbonitrile 1,4-di-N-oxide derivatives as hypoxic-cytotoxic agents
  作者：M Ortega

  DOI：10.1016/s0223-5234(00)00112-4

  日期：2000.1

  We report the synthesis and biological in vitro activities of 16 new 2-quinoxalinecarbonitrile 1,4-di-N-oxides. These compounds present new basic lateral chains (piperazines and anilines) in the 3 position as well as different substituents in the 6 and/or 7 positions of the quinoxaline ring. Among piperazine derivatives, 4b (a 7-chloro-3-(4-methylpiperaiin-1-yl) derivative) was the most potent (P = 0.5 x 10(-6) M). In general, aniline derivatives were more potent and selective than the former, compound 12b (with a 4-(methylphenyl)amino moiety in the 3 position and a chlorine atom in the 7 position) being the best one (P = 3 x 10-6 M and HCR > 16). (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• Aldana, Ignacio; Ortega; Jaso, Pharmazie, 2003, vol. 58, # 1, p. 68 - 69
  作者：Aldana, Ignacio、Ortega、Jaso、Zarranz、Oporto、Gimenez、Monge、Deharo

  DOI：——

  日期：——