(1S,3aS,7aS)-methyl 1-(Isoquinolin-7-yl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate | 1388055-28-4

• 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: (1S,3aS,7aS)-methyl 1-(Isoquinolin-7-yl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate
• 英文别名: (1R,3aS,7aS)-methyl1-(isoquinolin-7-yl)-7a-methyl-2,3,3a,7a-tetrahydro-1H-indene-5-carboxylate；methyl (1S,3aS,7aS)-1-isoquinolin-7-yl-7a-methyl-1,2,3,3a,6,7-hexahydroindene-5-carboxylate
• CAS: 1388055-28-4
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: GSCROILANDBOKH-ZVDOUQERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3aS,7aS)-methyl 1-(Isoquinolin-7-yl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate 在 L-Selectride 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 乙二胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 22.5h， 生成 (3S,3aR,11aS,11bR)-3-(isoquinolin-7-yl)-3a-methyl-1,3,3a,4,5,8,9,10,11a,11b-decahydrocyclopenta[c]xanthen-7(2H)-one
  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：

  (1R,3aS,7aS)-1-(isoquinolin-7-yl)-7a-methyl-2,3,3a,7a-tetrahydro-1H-inden-5-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 potassium diazodicarboxylate 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (1S,3aS,7aS)-methyl 1-(Isoquinolin-7-yl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-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

文献信息

• Synthetic Studies of Cortistatin A Analogue from the CD-Ring Fragment of Vitamin D<sub>2</sub>
  作者：Naoyuki Kotoku、Kohei Mizushima、Satoru Tamura、Motomasa Kobayashi

  DOI：10.1248/cpb.c13-00375

  日期：——

  Syntheses of analogue compounds of cortistatin A (1), an anti-angiogenic steroidal alkaloid from Indonesian marine sponge, were investigated by utilizing the CD-ring fragment of vitamin D₂. The incidental preparation of a new analogue having CD-cis-fused skeleton and its biological evaluation revealed the importance of the CD-trans-fused structure for the potent and selective antiproliferative activity

  利用维生素D 2的CD环片段，研究了来自印尼海洋海绵的抗血管生成甾体生物碱类皮质抑素A（1）的类似化合物的合成。附带的具有CD-顺式融合骨架的新类似物的附带制备及其生物学评估表明，CD融合结构对于1对人脐静脉内皮细胞（HUVEC）的有效和选择性抗增殖活性至关重要。
• 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.