2,6-二氢-6-甲基-2-beta-D-呋喃核糖基-1,2,3,5,6,7-六氮杂苊烯-8-胺 | 109947-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,6-二氢-6-甲基-2-beta-D-呋喃核糖基-1,2,3,5,6,7-六氮杂苊烯-8-胺
• 英文名称: 8-amino-6-N-methyl-2-(β-D-ribofuranosyl)-1,2,3,5,6,7-hexaazaacenaphtylene
• 英文别名: 8-amino-6-N-methyl-2-β-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene；8-Amino-6(N)-methyl-2-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene；(2R,3R,4S,5R)-2-(11-amino-9-methyl-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: 109947-70-8
• 化学式: C₁₂H₁₅N₇O₄
• 分子量: 321.296
• InChiKey: QQTLSGPMECXWPS-BFAGERDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,6-二氢-6-甲基-2-beta-D-呋喃核糖基-1,2,3,5,6,7-六氮杂苊烯-8-胺 在 吡啶 、 sodium tetrahydroborate 、 乙酸酐 、 二甲基亚砜 作用下， 以 乙醇 为溶剂， 反应 25.5h， 生成 8-amino-6-N-methyl-2-(3,5-O-(tetraisopropyldisiloxandiyl)-β-D-arabinofuranosyl)-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-4-(methylsulfonyl)-6-N-methyl-2-β-D-ribofuranosyl-1,2,3,5,6,7-hexaazaacenaphthylene 在 mercury(II) oxide 、 肼 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 2,6-二氢-6-甲基-2-beta-D-呋喃核糖基-1,2,3,5,6,7-六氮杂苊烯-8-胺
  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

• An unusual reductive ring-opening of the 1,2,3,5,6,7-hexaazaacenaphthylene ring system
  作者：Andrew M. Kawasaki、Leroy B. Townsend

  DOI：10.1016/s0040-4039(00)99223-2

  日期：1989.1

  Studies on an unexpected reaction involving a reductive cleavage of the pyridazine moiety of a tricyclic heterocycle are described. Structure assignments for the products obtained from the reductive cleavage were made using physicochemical methods.

  描述了对涉及三环杂环的哒嗪部分的还原性切割的意外反应的研究。由还原裂解获得的产物的结构分配是使用物理化学方法进行的。
• 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：——
• 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
  作者：Andrew M. Kawasaki、Linda L. Wotring、Leroy B. Townsend

  DOI：10.1021/jm00174a012

  日期：1990.12

  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.