Adenosin-5'-methylphosphonat | 3768-16-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: Adenosin-5'-methylphosphonat
• 英文别名: alpha-Methylene adenosine monophosphate；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-methylphosphinic acid
• CAS: 3768-16-9
• 化学式: C₁₁H₁₆N₅O₆P
• 分子量: 345.252
• InChiKey: PXSSQXBLDTZHLF-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  166
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Methyl-phosphonic acid (3aR,4R,6R,6aR)-6-(6-azido-purin-9-yl)-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester benzyl ester 在 palladium on activated charcoal 氢气 作用下， 生成 Adenosin-5'-methylphosphonat
  参考文献：
  名称：

  通过Mitsunobu反应合成5'-磷酸腺苷和5'-烷基膦酸酯

  摘要：

  Mitsunobu反应可以成功地用于实现嘌呤核苷的磷酸化和膦酰化。获得了一系列不同的具有良好至优异产率的不同的腺苷-5'-磷酸类似物。

  DOI：

  10.1016/0040-4039(95)00234-4

文献信息

• 5'-ALKYLPHOSPHONYLNUCLEOSIDES AS ANTIVIRALS
  申请人：FARMITALIA CARLO ERBA S.p.A.

  公开号：EP0445258A1

  公开（公告）日：1991-09-11
• Adenylation Enzyme Inhibitors
  申请人：Stichting Het Nederlands Kanker Instituut - antoni van Leeuwenhoek Ziekenhuis

  公开号：US20170327549A1

  公开（公告）日：2017-11-16

  The present invention concerns compounds that are capable of covalently entrapping adenylating enzymes. The present invention is essentially based on the discovery that analogues of adenylating enzyme (AE) substrates, wherein a methylene group has been incorporated at the carbon atom in the α-position relative to the carboxylate group involved in the adenylation, are capable of undergoing the adenylation reaction, thereby creating an activated methylene group in situ. The resulting ‘armed’ acyladenylate can interact with the enzyme resulting in covalent entrapment. Interestingly, the acyladenylate can alternatively be transferred to the next step in the enzyme cascade, following which the activated methylene group can interact with the next (active site cysteine containing) enzyme in the enzymatic cascade. The AE substrate analogues, based on their capability of ‘entrapping’ the respective enzymes, will have utility as activity based probes in biological research and also as diagnostic and/or therapeutic agents.
• [EN] 5'-ALKYLPHOSPHONYLNUCLEOSIDES AS ANTIVIRALS
  申请人：FARMITALIA CARLO ERBA S.R.L.

  公开号：WO1991004261A1

  公开（公告）日：1991-04-04

  (EN) The present invention relates to the use as antivirals of compounds of formula (I), wherein B is a purinic or pyrimidinic heterocycle; X is oxygen or sulphur; R1 is a hydroxyl group or a hydrogen atom; R2 is a linear, branched or cyclic, alkyl group of up to twenty carbon atoms; R3 is as specified for R2 above or a hydrogen atom, a cation or a polyhydroxy group.(FR) On prévoit l'utilisation en tant qu'agents antiviraux des composés de formule (I), où B est un hétérocycle purique ou pyrimidique; X est oxygène ou soufre; R1 est un groupe hydroxyle ou un atome d'hydrogène; R2 est un groupe alkyle linéaire, ramifié ou cyclique possédant jusqu'à vingt atomes de carbone; R3 est le même que R2 ci-dessus ou est un atome d'hydrogène, un cation ou un groupe polyhydroxy.
• Synthesis of adenosine-5′-phosphates and 5′-alkylphosphonates via the Mitsunobu reaction
  作者：Mourad Saady、Luc Lebeau、Charles Mioskowski

  DOI：10.1016/0040-4039(95)00234-4

  日期：1995.3

  The Mitsunobu reaction can be successfully applied to achieve phosphorylation and phosphonylation of purine nucleosides. A series of different adenosine-5′-phosphate analogs was obtained with good to excellent yields.

  Mitsunobu反应可以成功地用于实现嘌呤核苷的磷酸化和膦酰化。获得了一系列不同的具有良好至优异产率的不同的腺苷-5'-磷酸类似物。