8-fluoro-9-chlorosulfonyl-5,6-dihydro-5-oxo-11H-indenp[1,2-c]isoquinoline | 864063-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 8-fluoro-9-chlorosulfonyl-5,6-dihydro-5-oxo-11H-indenp[1,2-c]isoquinoline
• 英文别名: 8-Fluoro-5-oxo-6,11-dihydroindeno[1,2-c]isoquinoline-9-sulfonyl chloride
• CAS: 864063-40-1
• 化学式: C₁₆H₉ClFNO₃S
• 分子量: 349.77
• InChiKey: TWQNJIXCSOCAKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-fluoro-9-chlorosulfonyl-5,6-dihydro-5-oxo-11H-indenp[1,2-c]isoquinoline 、 N-(3-氨丙基)吗啉 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以45%的产率得到8-Fluoro-5-oxo-5,11-dihydro-6H-indeno[1,2-c]isoquinoline-9-sulfonic acid (3-morpholin-4-yl-propyl)-amide
  参考文献：
  名称：

  Discovery of Potent Poly(ADP-ribose) Polymerase-1 Inhibitors from the Modification of Indeno[1,2-c]isoquinolinone

  摘要：

  Novel indeno[1,2-c]isoquinolinone derivatives were synthesized and evaluated as inhibitors of the nuclear enzyme poly(ADP-ribose) polymerase-1 (PARP-1). These potent nonmutagenic PARP-1 inhibitors possess an additional five-membered ring between the B and C rings of 6(5H)-phenanthridinone. The most potent PARP-1 inhibitors were obtained from the substitution of the D ring at the C-9 position, in particular sulfonamide and N-acyl analogues (6 and 11). The 9-sulfonamide analogues 11a and 12a exhibited IC50 values of 1 and 10 nM, respectively.

  DOI：

  10.1021/jm0502891
• 作为产物：
  描述：

  5,6-dihydro-5-oxo-8-fluoro-indeno[1,2-c]isoquinoline 在 磺酰氯 作用下， 反应 0.75h， 以80%的产率得到8-fluoro-9-chlorosulfonyl-5,6-dihydro-5-oxo-11H-indenp[1,2-c]isoquinoline
  参考文献：
  名称：

  Discovery of Potent Poly(ADP-ribose) Polymerase-1 Inhibitors from the Modification of Indeno[1,2-c]isoquinolinone

  摘要：

  Novel indeno[1,2-c]isoquinolinone derivatives were synthesized and evaluated as inhibitors of the nuclear enzyme poly(ADP-ribose) polymerase-1 (PARP-1). These potent nonmutagenic PARP-1 inhibitors possess an additional five-membered ring between the B and C rings of 6(5H)-phenanthridinone. The most potent PARP-1 inhibitors were obtained from the substitution of the D ring at the C-9 position, in particular sulfonamide and N-acyl analogues (6 and 11). The 9-sulfonamide analogues 11a and 12a exhibited IC50 values of 1 and 10 nM, respectively.

  DOI：

  10.1021/jm0502891

文献信息

• Discovery of Potent Poly(ADP-ribose) Polymerase-1 Inhibitors from the Modification of Indeno[1,2-<i>c</i>]isoquinolinone
  作者：Prakash G. Jagtap、Erkan Baloglu、Garry J. Southan、Jon G. Mabley、Hongshan Li、Jing Zhou、John van Duzer、Andrew L. Salzman、Csaba Szabó

  DOI：10.1021/jm0502891

  日期：2005.8.1

  Novel indeno[1,2-c]isoquinolinone derivatives were synthesized and evaluated as inhibitors of the nuclear enzyme poly(ADP-ribose) polymerase-1 (PARP-1). These potent nonmutagenic PARP-1 inhibitors possess an additional five-membered ring between the B and C rings of 6(5H)-phenanthridinone. The most potent PARP-1 inhibitors were obtained from the substitution of the D ring at the C-9 position, in particular sulfonamide and N-acyl analogues (6 and 11). The 9-sulfonamide analogues 11a and 12a exhibited IC50 values of 1 and 10 nM, respectively.