dimethyl 7-(benzyloxycarbonylamino)-5-chloroquinoline-2,4-dicarboxylate | 1353988-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: dimethyl 7-(benzyloxycarbonylamino)-5-chloroquinoline-2,4-dicarboxylate
• 英文别名: Dimethyl 5-chloro-7-(phenylmethoxycarbonylamino)quinoline-2,4-dicarboxylate
• CAS: 1353988-79-0
• 化学式: C₂₁H₁₇ClN₂O₆
• 分子量: 428.829
• InChiKey: QNAFOBIAGVKOQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 7-(benzyloxycarbonylamino)-5-chloroquinoline-2,4-dicarboxylate 在 N-氯代丁二酰亚胺 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 65.0 ℃ 、206.85 kPa 条件下， 反应 3.0h， 生成 dimethyl 7-amino-5,8-dichloroquinoline-2,4-dicarboxylate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Potent Quinoline and Pyrroloquinoline Ammosamide Analogues as Inhibitors of Quinone Reductase 2

  摘要：

  A variety of ammosamide B analogues have been synthesized and evaluated as inhibitors of quinone reductase 2 (QR2). The potencies of the resulting series of QR2 inhibitors range from 4.1 to 25,200 nM. The data provide insight into the structural parameters necessary for QR2 inhibitory activity. The natural product ammosamide B proved to be a potent QR2 inhibitor, and the potencies of the analogues generally decreased as their structures became more distinct from that of ammosamide B. Methylation of the 8-amino group of ammosamide B was an exception, resulting in an increase in quinone reductase 2 inhibitory activity from an IC50 of 61 nM to IC50 4.1 nM.

  DOI：

  10.1021/jm201251c
• 作为产物：
  描述：

  benzyl 3-amino-5-chlorophenylcarbamate 、 (E)-2-氧代戊烯二酸二甲酯 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 dimethyl 7-(benzyloxycarbonylamino)-5-chloroquinoline-2,4-dicarboxylate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Potent Quinoline and Pyrroloquinoline Ammosamide Analogues as Inhibitors of Quinone Reductase 2

  摘要：

  A variety of ammosamide B analogues have been synthesized and evaluated as inhibitors of quinone reductase 2 (QR2). The potencies of the resulting series of QR2 inhibitors range from 4.1 to 25,200 nM. The data provide insight into the structural parameters necessary for QR2 inhibitory activity. The natural product ammosamide B proved to be a potent QR2 inhibitor, and the potencies of the analogues generally decreased as their structures became more distinct from that of ammosamide B. Methylation of the 8-amino group of ammosamide B was an exception, resulting in an increase in quinone reductase 2 inhibitory activity from an IC50 of 61 nM to IC50 4.1 nM.

  DOI：

  10.1021/jm201251c