cyclohexa[1,2-d]-2,3,3a,11a-tetrahydro-3-hydroxy-2-hydroxymethyl-10H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-10-one | 1215184-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: cyclohexa[1,2-d]-2,3,3a,11a-tetrahydro-3-hydroxy-2-hydroxymethyl-10H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-10-one
• 英文别名: (11R,13R,14R,15S)-14-hydroxy-13-(hydroxymethyl)-12,16-dioxa-2,10-diazatetracyclo[8.6.0.03,8.011,15]hexadeca-1,3(8)-dien-9-one
• CAS: 1215184-85-2
• 化学式: C₁₃H₁₆N₂O₅
• 分子量: 280.28
• InChiKey: SSWSVUANSUPVIV-MWGHHZFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cyclohexa[1,2-d]-2,3,3a,11a-tetrahydro-3-hydroxy-2-hydroxymethyl-10H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-10-one 在 sodium ethanolate 、 盐酸 、 水 作用下， 以 乙醇 为溶剂， 以13%的产率得到3-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5,6,7,8-tetrahydroquinazoline-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：

  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 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以80%的产率得到cyclohexa[1,2-d]-2,3,3a,11a-tetrahydro-3-hydroxy-2-hydroxymethyl-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