cyclohexa[1,2-e]-2,3,3a,11a-tetrahydro-3-(O-tertbutyldimethylsilyl)-2-(O-tert-butyldimethylsilylmethyl)-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one | 1215184-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexa[1,2-e]-2,3,3a,11a-tetrahydro-3-(O-tertbutyldimethylsilyl)-2-(O-tert-butyldimethylsilylmethyl)-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
• 英文别名: (12S,13R,14R,16R)-13-[tert-butyl(dimethyl)silyl]oxy-14-[[tert-butyl(dimethyl)silyl]oxymethyl]-11,15-dioxa-1,9-diazatetracyclo[8.6.0.02,7.012,16]hexadeca-2(7),9-dien-8-one
• CAS: 1215184-84-1
• 化学式: C₂₅H₄₄N₂O₅Si₂
• 分子量: 508.806
• InChiKey: SRFWKCLHOKHDMN-XWSHUIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cyclohexa[1,2-e]-2,3,3a,11a-tetrahydro-3-(O-tertbutyldimethylsilyl)-2-(O-tert-butyldimethylsilylmethyl)-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以100%的产率得到cyclohexa[1,2-e]-2,3,3a,11a-tetrahydro-3-hydroxy-2-hydroxymethyl-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
  参考文献：
  名称：

  Synthesis and in vitro cytostatic activity of new β - d -arabino furan[1′,2′:4,5]oxazolo- and arabino-pyrimidinone derivatives

  摘要：

  A series of nucleoside derivatives was obtained via heteroatom annulation of the amino oxazoline Of D(-)-arabinose. Unequivocal proofs for the stereostructure of some new arabinosyl pyrimidinone derivatives were obtained by X-ray structure analysis. These newly synthesized compounds were then evaluated for their cytostatic activity against murine leukemia (L1210), and human T-lymphocytes (Molt 4/C8 and CEM). Of all the compounds in the series, the protected silylated tricyclic fused pyrimidinone 10 showed the most significant antitumor activity against murine leukemia L1210 (IC50 = 6 mu M), and human T-lymphocytes cells Molt 4/C8 (IC50 = 7.9 mu M) and CEM/0 cell lines (IC50 = 7.5 mu M). None of the compounds exhibited significant antiviral inhibitory activities. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.032
• 作为产物：
  描述：

  2-环己酮甲酸乙酯 、 2-amino-3',5'-bis(O-t-butyldimethylsilyl)-β-D-arabinofurano<1',2':4,5>-2-oxazoline 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 5.0h， 以41%的产率得到cyclohexa[1,2-d]-2,3,3a,11a-tetrahydro-3-(O-tertbutyldimethylsilyl)-2-(O-tert-butyldimethylsilylmethyl)-10H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-10-one
  参考文献：
  名称：

  Synthesis and in vitro cytostatic activity of new β - d -arabino furan[1′,2′:4,5]oxazolo- and arabino-pyrimidinone derivatives

  摘要：

  A series of nucleoside derivatives was obtained via heteroatom annulation of the amino oxazoline Of D(-)-arabinose. Unequivocal proofs for the stereostructure of some new arabinosyl pyrimidinone derivatives were obtained by X-ray structure analysis. These newly synthesized compounds were then evaluated for their cytostatic activity against murine leukemia (L1210), and human T-lymphocytes (Molt 4/C8 and CEM). Of all the compounds in the series, the protected silylated tricyclic fused pyrimidinone 10 showed the most significant antitumor activity against murine leukemia L1210 (IC50 = 6 mu M), and human T-lymphocytes cells Molt 4/C8 (IC50 = 7.9 mu M) and CEM/0 cell lines (IC50 = 7.5 mu M). None of the compounds exhibited significant antiviral inhibitory activities. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.032