Methyl 11-amino-10-chloro-2-methyl-9-(methylamino)-3-oxo-2,7-diazatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene-6-carboxylate | 1353989-34-0

• 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: Methyl 11-amino-10-chloro-2-methyl-9-(methylamino)-3-oxo-2,7-diazatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene-6-carboxylate
• CAS: 1353989-34-0
• 化学式: C₁₄H₁₃ClN₄O₃
• 分子量: 320.735
• InChiKey: ZOLSLHFVGPQCHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 11-amino-10-chloro-2-methyl-9-(methylamino)-3-oxo-2,7-diazatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene-6-carboxylate 在 ammonium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以80%的产率得到8-amino-7-chloro-6-(methylamino)-2-oxo-1,2-dihydropyrrolo[4,3,2-d,e]quinoline-4-carboxamide
  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：

  methyl 6,8-diamino-7-chloro-2-oxo-1,2-dihydropyrrolo[4,3,2-de]quinoline-4-carboxylate 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到ammosamide B
  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

文献信息

• Design, Synthesis, and Biological Evaluation of Potent Quinoline and Pyrroloquinoline Ammosamide Analogues as Inhibitors of Quinone Reductase 2
  作者：P. V. Narasimha Reddy、Katherine C. Jensen、Andrew D. Mesecar、Phillip E. Fanwick、Mark Cushman

  DOI：10.1021/jm201251c

  日期：2012.1.12

  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.