7-acetyl-2,3,3a,9a-tetrahydro-3-hydroxy-2-hydroxymethyl-8H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-8-one | 1215184-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-acetyl-2,3,3a,9a-tetrahydro-3-hydroxy-2-hydroxymethyl-8H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-8-one
• 英文别名: (2R,4R,5R,6S)-11-acetyl-5-hydroxy-4-(hydroxymethyl)-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,10-dien-12-one
• CAS: 1215184-75-0
• 化学式: C₁₁H₁₂N₂O₆
• 分子量: 268.226
• InChiKey: AIZNNQNCNGTPJT-BDNRQGISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-acetyl-2,3,3a,9a-tetrahydro-3-hydroxy-2-hydroxymethyl-8H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-8-one 在 sodium ethanolate 、 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以25%的产率得到5-acetyl-3-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione
  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：

  N'-(6-hydroxy-5-hydroxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3oxazol-2-yl]-N,N-dimethylimidoformamide 、 2,2,6-三甲基-4H-1,3-二英-4-酮 以 丙酮 为溶剂， 反应 2.0h， 以17%的产率得到7-acetyl-2,3,3a,9a-tetrahydro-3-hydroxy-2-hydroxymethyl-8H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-8-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

文献信息

• Synthesis and in vitro cytostatic activity of new β - d -arabino furan[1′,2′:4,5]oxazolo- and arabino-pyrimidinone derivatives
  作者：Jean-Jacques Bosc、Laurent Latxague、Jean-Michel Léger、Jan Balzarini、Isabelle Forfar、Christian Jarry、Jean Guillon

  DOI：10.1016/j.ejmech.2009.10.032

  日期：2010.2

  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.