2-amino-N⁶-amino-N⁶-methyladenosine

• 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-amino-N⁶-methyladenosine
• 英文别名: 1-[2-amino-6-(N-methyl-hydrazino)-purin-9-yl]-β-D-1-deoxy-ribofuranose；2-amino-N6-amino-N6-methyladenosine；2-Amino-6-(1-methyl-hydrazino)-9-β-D-ribofuranosyl-purin；(2R,3R,4S,5R)-2-[2-amino-6-[amino(methyl)amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₁₁H₁₇N₇O₄
• 分子量: 311.3
• InChiKey: NFFGTXCRIHHQGF-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  6-氯鸟嘌呤核苷 、 甲基肼 以 乙醇 、 水 为溶剂， 以83%的产率得到2-amino-N⁶-amino-N⁶-methyladenosine
  参考文献：
  名称：

  Anti-malarial activity of N6-modified purine analogues

  摘要：

  Plasmodium falciparum causes one of the deadliest forms of malaria and resistance to the currently available drugs makes it imperative to develop new, safe and potent drugs. Parasites such as P. falciparum are unable to synthesise purines de novo and to this end often have multiple purine uptake and salvage systems. With this in mind, we have designed and synthesised libraries of purine analogues as potential anti-malarial agents. Herein, we report three compounds with promising activity against the highly chloroquine-resistant VS1 P. falciparum namely: N-6-hydroxyadenine (1c), 2-amino-N-6-aminoadenosine (2b) and 2-amino-N-6-amino-N-6-methyladenosine (4b). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.038

文献信息

• WO2007/135380
  申请人：——

  公开号：——

  公开（公告）日：——
• Anti-malarial activity of N6-modified purine analogues
  作者：Kathleen Too、Daniel M. Brown、Emily Bongard、Vanessa Yardley、Livia Vivas、David Loakes

  DOI：10.1016/j.bmc.2007.05.038

  日期：2007.8

  Plasmodium falciparum causes one of the deadliest forms of malaria and resistance to the currently available drugs makes it imperative to develop new, safe and potent drugs. Parasites such as P. falciparum are unable to synthesise purines de novo and to this end often have multiple purine uptake and salvage systems. With this in mind, we have designed and synthesised libraries of purine analogues as potential anti-malarial agents. Herein, we report three compounds with promising activity against the highly chloroquine-resistant VS1 P. falciparum namely: N-6-hydroxyadenine (1c), 2-amino-N-6-aminoadenosine (2b) and 2-amino-N-6-amino-N-6-methyladenosine (4b). (c) 2007 Elsevier Ltd. All rights reserved.