2-amino-N6-methoxy-N6-methyl-9-(3-C-methyl-β-D-ribofuranosyl)adenine | 1298095-30-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-amino-N6-methoxy-N6-methyl-9-(3-C-methyl-β-D-ribofuranosyl)adenine
• 英文别名: (2R,3S,4R,5R)-5-[2-amino-6-[methoxy(methyl)amino]purin-9-yl]-2-(hydroxymethyl)-3-methyloxolane-3,4-diol
• CAS: 1298095-30-3
• 化学式: C₁₃H₂₀N₆O₅
• 分子量: 340.339
• InChiKey: ZIOQMKDUVFVUOH-HUHPYQOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  6-chloro-9-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)-9H-purin-2-amine 在 甲醇 、 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 2-amino-N6-methoxy-N6-methyl-9-(3-C-methyl-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3′-C-methyl-ribonucleosides as antitumor agents

  摘要：

  A series of N-6-aminopurine-9-beta-D-ribonucleosides and ribose-modified 3'-C-methyl analogues substituted at N-6-position with a small group like hydroxy, methoxy or amino group or at C2(N-6) position have been synthesized and tested against a panel of human leukemia and carcinoma cell lines. N-6-Hydrazino-9-beta-D-ribofuranosyl-Purine (5) displayed the best antiproliferative activity in the low micromolar or submicromolar range against all tested tumor cell lines. The activity of this nucleoside is related in part to ribonucleotide reductase inhibition. C2-modification or 3'-C-methylation in N-6-substituted adenosine analogues leads to a decrease or loss in activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.055

文献信息

• Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3′-C-methyl-ribonucleosides as antitumor agents
  作者：Loredana Cappellacci、Riccardo Petrelli、Palmarisa Franchetti、Patrizia Vita、Praveen Kusumanchi、Mohineesh Kumar、Hiremagalur N. Jayaram、Bingsen Zhou、Yun Yen、Mario Grifantini

  DOI：10.1016/j.ejmech.2011.01.055

  日期：2011.5

  A series of N-6-aminopurine-9-beta-D-ribonucleosides and ribose-modified 3'-C-methyl analogues substituted at N-6-position with a small group like hydroxy, methoxy or amino group or at C2(N-6) position have been synthesized and tested against a panel of human leukemia and carcinoma cell lines. N-6-Hydrazino-9-beta-D-ribofuranosyl-Purine (5) displayed the best antiproliferative activity in the low micromolar or submicromolar range against all tested tumor cell lines. The activity of this nucleoside is related in part to ribonucleotide reductase inhibition. C2-modification or 3'-C-methylation in N-6-substituted adenosine analogues leads to a decrease or loss in activity. (C) 2011 Elsevier Masson SAS. All rights reserved.