(3R,3'aR,5'aS,9'bS)-3-(3-bromo-4-methoxyphenyl)-5'a,9'-dimethyl-2-phenylspiro[1,2-oxazolidine-5,3'-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran]-2',8'-dione | 1443017-72-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3R,3'aR,5'aS,9'bS)-3-(3-bromo-4-methoxyphenyl)-5'a,9'-dimethyl-2-phenylspiro[1,2-oxazolidine-5,3'-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran]-2',8'-dione
• CAS: 1443017-72-8
• 化学式: C₂₉H₂₈BrNO₅
• 分子量: 550.449
• InChiKey: WUQVYYITCVOYDQ-XXFKYZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-1-(3-bromo-4-methoxyphenyl)-N-phenylmethanimine oxide 、 (3aS,5aS,9bS)-5a,9-dimethyl-3-methylene-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione 以 苯 为溶剂， 反应 8.0h， 以20%的产率得到
  参考文献：
  名称：

  Synthesis and anticancer activity of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of α-santonin

  摘要：

  In the present study, novel Spiro derivatives of alpha-santonin were prepared and tested for their anticancer activity against a panel of six human cancer cell lines. Spiro-isoxazoline and spiro-isoxazolidine derivatives have been generated on C-ring of alpha-santonin (alpha-methylene-gamma-butyrolactone) by the 1,3-dipolar cycloaddition of alpha-santonin derivative 6 with nitrile oxides 7 and nitrones 9 respectively. Among all, compound 10b '' had shown IC50 of 0.01, 0.5 and 0.3 mu M against PC-3, THP-1 and MCF-7 cell lines respectively. Further, flow cytometry studies showed that PC-3 cells treated with the spiro-isoxazolidine derivative 10b '' were arrested in the sub G1 phase of the cell cycle in a concentration dependent manner. The spiro-isoxazolidine derivative 10b '' also showed concentration dependent inhibitory activity against NF-kappa B, p65 with 57% inhibition in 24 h at 10 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.003

文献信息

• Synthesis and anticancer activity of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of α-santonin
  作者：Jabeena Khazir、Parvinder Pal Singh、D. Mahendhar Reddy、Irfan Hyder、Syed Shafi、S.D. Sawant、Gousia Chashoo、Ajay Mahajan、M.S. Alam、A.K. Saxena、S. Arvinda、B.D. Gupta、H.M. Sampath Kumar

  DOI：10.1016/j.ejmech.2013.01.003

  日期：2013.5

  In the present study, novel Spiro derivatives of alpha-santonin were prepared and tested for their anticancer activity against a panel of six human cancer cell lines. Spiro-isoxazoline and spiro-isoxazolidine derivatives have been generated on C-ring of alpha-santonin (alpha-methylene-gamma-butyrolactone) by the 1,3-dipolar cycloaddition of alpha-santonin derivative 6 with nitrile oxides 7 and nitrones 9 respectively. Among all, compound 10b '' had shown IC50 of 0.01, 0.5 and 0.3 mu M against PC-3, THP-1 and MCF-7 cell lines respectively. Further, flow cytometry studies showed that PC-3 cells treated with the spiro-isoxazolidine derivative 10b '' were arrested in the sub G1 phase of the cell cycle in a concentration dependent manner. The spiro-isoxazolidine derivative 10b '' also showed concentration dependent inhibitory activity against NF-kappa B, p65 with 57% inhibition in 24 h at 10 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.