(1R,3aS,7aR)-1-(isoquinolin-7-yl)-7a-methyl-2,3,3a,4-tetrahydro-1H-inden-5(7aH)-one | 1366053-28-2

• 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: (1R,3aS,7aR)-1-(isoquinolin-7-yl)-7a-methyl-2,3,3a,4-tetrahydro-1H-inden-5(7aH)-one
• 英文别名: (1R,3aS,7aR)-1-isoquinolin-7-yl-7a-methyl-2,3,3a,4-tetrahydro-1H-inden-5-one
• CAS: 1366053-28-2
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: NMAOSGGFLPNCMQ-UHOSZYNNSA-N

物化性质

• 沸点：
  454.9±34.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3aS,7aR)-1-(isoquinolin-7-yl)-7a-methyl-2,3,3a,4-tetrahydro-1H-inden-5(7aH)-one 在 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (1R,3aS,7aS)-methyl 1-(isoquinolin-7-yl)-7a-methyl-2,3,3a,7a-tetrahydro-1H-indene-5-carboxylate
  参考文献：
  名称：

  Creation of Readily Accessible and Orally Active Analogue of Cortistatin A

  摘要：

  Syntheses of structurally simplified analogues of cortistatin A (1), a novel antiangiogenic steroidal alkaloid from Indonesian marine sponge, and their biological activities were investigated. The analogues were designed by considering the 3-D structure of 1. Compound 30, in which the isoquinoline moiety was appended to the planar tetracyclic core structure, showed potent antiproliferative activity against human umbilical vein endothelial cells (HUVECs) together with high selectivity and also showed in vivo antiangiogenic activity and significant antitumor effect by oral administration.

  DOI：

  10.1021/ml300143d
• 作为产物：
  描述：

  (1S,3aS,7aS)-1-(isoquinolin-7-yl)-7a-methylhexahydro-1H-inden-5(6H)-one 在 三甲基氯硅烷 、 六甲基二硅氮烷 、 sodium iodide 、 2-碘酰基苯甲酸 作用下， 以 乙腈 、 二甲基亚砜 为溶剂， 反应 11.0h， 以71%的产率得到(1R,3aS,7aR)-1-(isoquinolin-7-yl)-7a-methyl-2,3,3a,4-tetrahydro-1H-inden-5(7aH)-one
  参考文献：
  名称：

  NOVEL CORTISTATIN A ANALOG AND USE THEREOF

  摘要：

  公开号：

  EP2617720B1

文献信息

• NOVEL CORTISTATIN A ANALOG AND USE THEREOF
  申请人：Osaka University

  公开号：EP2617720B1

  公开（公告）日：2016-03-30
• US8791263B2
  申请人：——

  公开号：US8791263B2

  公开（公告）日：2014-07-29
• Creation of Readily Accessible and Orally Active Analogue of Cortistatin A
  作者：Naoyuki Kotoku、Yuji Sumii、Takeshi Hayashi、Satoru Tamura、Takashi Kawachi、Sho Shiomura、Masayoshi Arai、Motomasa Kobayashi

  DOI：10.1021/ml300143d

  日期：2012.8.9

  Syntheses of structurally simplified analogues of cortistatin A (1), a novel antiangiogenic steroidal alkaloid from Indonesian marine sponge, and their biological activities were investigated. The analogues were designed by considering the 3-D structure of 1. Compound 30, in which the isoquinoline moiety was appended to the planar tetracyclic core structure, showed potent antiproliferative activity against human umbilical vein endothelial cells (HUVECs) together with high selectivity and also showed in vivo antiangiogenic activity and significant antitumor effect by oral administration.