methyl (2R)-2-[[2-(6-aminopurin-9-yl)ethoxymethyl-phenoxy-phosphoryl]amino]propanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2R)-2-[[2-(6-aminopurin-9-yl)ethoxymethyl-phenoxy-phosphoryl]amino]propanoate
• 英文别名: methyl (2R)-2-[[2-(6-aminopurin-9-yl)ethoxymethyl-phenoxyphosphoryl]amino]propanoate
• 化学式: C₁₈H₂₃N₆O₅P
• 分子量: 434.392
• InChiKey: JIQWPHCYEYORRP-SGSXECEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  10

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  阿德福韦	Adefovir	106941-25-7	C8H12N5O4P	273.188
  ——	dichloro-9-[2-(phosphorylmethoxy)ethaneyl]adenine	142341-38-6	C8H10Cl2N5O2P	310.079

反应信息

• 作为产物：
  描述：

  阿德福韦 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 32.5h， 生成 methyl (2R)-2-[[2-(6-aminopurin-9-yl)ethoxymethyl-phenoxy-phosphoryl]amino]propanoate
  参考文献：
  名称：

  Synthesis and evaluation of novel amidate prodrugs of PMEA and PMPA

  摘要：

  Some novel amidate prodrugs of PMEA and PMPA have been synthesised and tested in vitro for their biological activity. Compound 5 in particular showed greatly enhanced antiviral potency compared with the parent nucleotide analogue. In vitro enzymatic studies and structure-activity relationships indicate that the degradation mechanism of such prodrugs may be the same as that described for the phosphoramidate triesters of nucleotide analogues. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00128-7

文献信息

• Synthesis and evaluation of novel amidate prodrugs of PMEA and PMPA
  作者：Carlo Ballatore、Christopher McGuigan、Erik De Clercq、Jan Balzarini

  DOI：10.1016/s0960-894x(01)00128-7

  日期：2001.4

  Some novel amidate prodrugs of PMEA and PMPA have been synthesised and tested in vitro for their biological activity. Compound 5 in particular showed greatly enhanced antiviral potency compared with the parent nucleotide analogue. In vitro enzymatic studies and structure-activity relationships indicate that the degradation mechanism of such prodrugs may be the same as that described for the phosphoramidate triesters of nucleotide analogues. (C) 2001 Elsevier Science Ltd. All rights reserved.