6-chloro-2-(4-chlorophenyl)quinoxaline 1,4-dioxide | 911839-05-9

• 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: 6-chloro-2-(4-chlorophenyl)quinoxaline 1,4-dioxide
• 英文别名: 7-Chloro-3-(4-chlorophenyl)-4-oxidoquinoxalin-1-ium 1-oxide
• CAS: 911839-05-9
• 化学式: C₁₄H₈Cl₂N₂O₂
• 分子量: 307.136
• InChiKey: AFOQBTDNZFDNFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 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：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯苯乙酮 、 5-氯苯并呋咱 3-氧化物 在 氨 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以60%的产率得到6-chloro-2-(4-chlorophenyl)quinoxaline 1,4-dioxide
  参考文献：
  名称：

  New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides

  摘要：

  Hypoxic cells which are common feature of solid tumors are resistant to both anticancer drugs and radiation therapy. Thus, the identification of drugs with the selective toxicity toward hypoxic cells is an important target in anticancer chemotherapy. Tirapazamine has been shown to be an efficient and selective cytotoxin after bioreductive activation in hypoxic cells which is thought to be due to the presence of the 1,4-di-N-oxide. A new series of quinoxaline 1,4-di-N-oxides and fused quinoxaline di-N-oxides were synthesized and evaluated for hypoxic-cytotoxic activity on EAC cell line. Compound 10a was the most potent cytotoxin IC50 0.9 mu g/mL, potency 75 mu g/mL, and was approximately 15 times more selective cytotoxin (HCR > 111) than 3-aminoquinoxaline-2-carbonitrile which has been used as a standard (HCR > 7.5). Compounds 4 and 3a,b were more selective than the standard. In addition, antitumor activity against Hepg2 (liver) and U251 (brain) human cell lines was evaluated, compounds 9c and 8a were the most active against Hepg2 with IC50 values 1.9 and 2.9 mu g/mL, respectively, however, all the tested compounds were nontoxic against U251 cell line. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.038

文献信息

• METHOD FOR TREATING A TUMOUR DISEASE AND METHOD FOR SELECTIVELY INHIBITING TUMOUR CELL GROWTH USING A QUINOXALINE-1,4-DIOXIDE DERIVATIVE
  申请人：OOO "A-Laboratory"

  公开号：EP3138565A1

  公开（公告）日：2017-03-08

  The present invention relates to the fields of pharmacology and medicine, in particular, to the medical application of 6,7-difluoro-3-phenyl-2-cyanoquinoxaline 1,4-dioxide of formula I: for inhibition of tumor cell growth or treatment of tumor diseases.

  本发明涉及药理学和医学领域，特别是涉及使用式I的6,7-二氟-3-苯基-2-氰基喹喔啉-1,4-二氧化物进行抑制肿瘤细胞生长或治疗肿瘤疾病的医学应用。
• New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides
  作者：Kamelia M. Amin、Magda M.F. Ismail、Eman Noaman、Dalia H. Soliman、Yousry A. Ammar

  DOI：10.1016/j.bmc.2006.06.038

  日期：2006.10

  Hypoxic cells which are common feature of solid tumors are resistant to both anticancer drugs and radiation therapy. Thus, the identification of drugs with the selective toxicity toward hypoxic cells is an important target in anticancer chemotherapy. Tirapazamine has been shown to be an efficient and selective cytotoxin after bioreductive activation in hypoxic cells which is thought to be due to the presence of the 1,4-di-N-oxide. A new series of quinoxaline 1,4-di-N-oxides and fused quinoxaline di-N-oxides were synthesized and evaluated for hypoxic-cytotoxic activity on EAC cell line. Compound 10a was the most potent cytotoxin IC50 0.9 mu g/mL, potency 75 mu g/mL, and was approximately 15 times more selective cytotoxin (HCR > 111) than 3-aminoquinoxaline-2-carbonitrile which has been used as a standard (HCR > 7.5). Compounds 4 and 3a,b were more selective than the standard. In addition, antitumor activity against Hepg2 (liver) and U251 (brain) human cell lines was evaluated, compounds 9c and 8a were the most active against Hepg2 with IC50 values 1.9 and 2.9 mu g/mL, respectively, however, all the tested compounds were nontoxic against U251 cell line. (c) 2006 Elsevier Ltd. All rights reserved.