8-amino-4-(methylsulfonyl)-6-N-methyl-2-β-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene | 129572-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-amino-4-(methylsulfonyl)-6-N-methyl-2-β-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene
• 英文别名: (2R,3R,4S,5R)-2-(11-amino-9-methyl-6-methylsulfonyl-2,3,5,7,9,10-hexazatricyclo[6.3.1.04,12]dodeca-1,4(12),5,7,10-pentaen-3-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 129572-01-6
• 化学式: C₁₃H₁₇N₇O₆S
• 分子量: 399.387
• InChiKey: PMLZQXHUAMDIEG-BFAGERDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  198
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  8-amino-4-(methylsulfonyl)-6-N-methyl-2-β-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 mercury(II) oxide 、 肼 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 39.5h， 生成 8-amino-6-N-methyl-2-(2-deoxy-3,5-O-(tetraisopropyldisiloxandiyl)-β-D-ribofuranosyl)-1,2,3,5,6,7-hexaazaacenaphthylene
  参考文献：
  名称：

  Synthesis and cytotoxicity studies of 8-amino-6-methyl-2-.beta.-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene (7-Aza-TCN) and the corresponding 2'-deoxy- and arabinonucleoside analogues

  摘要：

  The tricyclic nucleoside 8-amino-6-N-methyl-2-beta-D-ribofuranosyl-1,2,3,5,6, 7-hexaazaacenaphthylene was synthesized from 8-amino-6-N-methyl-4-(methylthio)-2-beta-D-ribofuranosyl-1,2,3,5,6, 7-hexaazaacenaphthylene. The 2'-deoxy analogue of 5, 8-amino-6-N-methyl-2-(2-deoxy-beta-D-ribofuranosyl)-1,2,3,5,6, 7-hexaazaacenaphthylene (11), and the arabino analogue of (5), 8-amino-6-N-methyl-2-beta-D-arabinofuranosyl-1,2,3,5,6, 7-hexaazaacenaphthylene (14) were synthesized from 5. Nucleosides 2,3,4,5,11, and 14 were evaluated for potential anticancer activity by measuring their ability to inhibit the growth of L1210 and H. Ep. 2 tumor cells in vitro.

  DOI：

  10.1021/jm00174a012
• 作为产物：
  描述：

  8-amino-6-N-methyl-4-(methylthio)-2-β-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene 在 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以75%的产率得到8-amino-4-(methylsulfonyl)-6-N-methyl-2-β-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene
  参考文献：
  名称：

  Synthesis and cytotoxicity studies of 8-amino-6-methyl-2-.beta.-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene (7-Aza-TCN) and the corresponding 2'-deoxy- and arabinonucleoside analogues

  摘要：

  The tricyclic nucleoside 8-amino-6-N-methyl-2-beta-D-ribofuranosyl-1,2,3,5,6, 7-hexaazaacenaphthylene was synthesized from 8-amino-6-N-methyl-4-(methylthio)-2-beta-D-ribofuranosyl-1,2,3,5,6, 7-hexaazaacenaphthylene. The 2'-deoxy analogue of 5, 8-amino-6-N-methyl-2-(2-deoxy-beta-D-ribofuranosyl)-1,2,3,5,6, 7-hexaazaacenaphthylene (11), and the arabino analogue of (5), 8-amino-6-N-methyl-2-beta-D-arabinofuranosyl-1,2,3,5,6, 7-hexaazaacenaphthylene (14) were synthesized from 5. Nucleosides 2,3,4,5,11, and 14 were evaluated for potential anticancer activity by measuring their ability to inhibit the growth of L1210 and H. Ep. 2 tumor cells in vitro.

  DOI：

  10.1021/jm00174a012

文献信息

• KAWASAKI, ANDREW M.;WOTRING, LINDA L.;TOWNSEND, LEROY B., J. MED. CHEM., 33,(1990) N2, C. 3170-3176
  作者：KAWASAKI, ANDREW M.、WOTRING, LINDA L.、TOWNSEND, LEROY B.

  DOI：——

  日期：——