(2R,3R,4S,5R)-2-(6-氨基-8-乙烯基嘌呤-9-基)-5-(羟基甲基)四氢呋喃-3,4-二醇 | 142386-40-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: (2R,3R,4S,5R)-2-(6-氨基-8-乙烯基嘌呤-9-基)-5-(羟基甲基)四氢呋喃-3,4-二醇
• 英文名称: 8-vinyladenosine
• 英文别名: (2R,3R,4S,5R)-2-(6-amino-8-ethenylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 142386-40-1
• 化学式: C₁₂H₁₅N₅O₄
• 分子量: 293.282
• InChiKey: XWDWYGMKPANXOO-JJNLEZRASA-N

物化性质

• 沸点：
  688.0±65.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  8-ethenyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)adenosine 在 氟化铵 作用下， 以 甲醇 为溶剂， 以50%的产率得到(2R,3R,4S,5R)-2-(6-氨基-8-乙烯基嘌呤-9-基)-5-(羟基甲基)四氢呋喃-3,4-二醇
  参考文献：
  名称：

  Synthesis and cytotoxic activity of 6-vinyl- and 6-ethynyluridine and 8-vinyl- and 8-ethynyladenosine

  摘要：

  It is well-known that the introduction of vinyl and ethynyl moieties into nucleosides is of crucial importance for cytostatic, antiviral, or other biological activities. In this study 6- and 8-vinyl-and -ethynyluridine and -adenosine were prepared by a general procedure involving the palladium-catalyzed cross-coupling of trimethylsilylacetylene or vinyltributyltin. The introduction of a vinyl group at C-6 of uridine or an ethynyl group at C-8 of adenosine resulted in nucleoside derivatives showing cytostatic activity against several murine and/or human tumor cell lines. Interestingly, 8-vinyladenosine had pronounced selective inhibitory effects on human (Molt/4F and MT-4) versus murine (L1210 and FM3A) tumor cell lines.

  DOI：

  10.1021/jm00001a025

文献信息

• Straightforward C-8 alkylation of adenosine analogues with tetraalkyltin reagents
  作者：Petros Mamos、Arthur A. Van Aerschot、nancy J. Weyns、Piet A. Herdewijn

  DOI：10.1016/s0040-4039(00)74226-2

  日期：1992.4

  A one step synthesis of the 8-methyl-, 8-ethyl -and 8-vinyl derivatives of adenosine, 2′-deoxyadenosine and 2′,3′-dideoxyadenosine starting from the readily available 8-bromo congeners is described. This reaction makes use of a transient silylation procedure and a Pd(0) catalysed cross-coupling with tetraorganotin reagents.

  描述了从容易获得的8-溴同源物开始的腺苷，2'-脱氧腺苷和2'，3'-二脱氧腺苷的8-甲基，8-乙基和8-乙烯基衍生物的一步合成。该反应利用了瞬态甲硅烷基化程序和Pd（0）催化与四有机锡试剂的交叉偶联。
• Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents
  作者：Arthur A. Van Aerschot、Petros Mamos、Nancy J. Weyns、Satoru Ikeda、Erik De Clercq、Piet A. Herdewijn

  DOI：10.1021/jm00072a013

  日期：1993.10

  2-, 6-, And 8-alkylated (methyl, ethyl, and vinyl) adenosine analogues were synthesized by a palladium-catalyzed cross-coupling of a tetraalkyltin with the halogenated purine nucleosides. The synthesis of the 8-substituted analogues was accomplished using a transient protection procedure. The 6-alkylated-9-beta-D-ribofuranosylpurines as well as 2-ethyladenosine were cytotoxic at relatively low concentrations

  通过将四烷基锡与卤代嘌呤核苷进行钯催化的交叉偶联，可合成2-，6-和8-烷基化（甲基，乙基和乙烯基）的腺苷类似物。8-取代类似物的合成使用瞬态保护程序完成。6烷基化的9-β-D-呋喃呋喃糖基嘌呤以及2-乙基腺苷在相对较低的浓度（0.8-10微克/ mL）下具有细胞毒性。8-甲基腺苷是牛痘病毒的有效和选择性抑制剂，而8-乙基和8-乙烯基腺苷对呼吸道合胞病毒具有特异性抑制作用。8-Vinyladenosine显示出对单纯疱疹病毒（1型）的特殊活性。
• US5580972A
  申请人：——

  公开号：US5580972A

  公开（公告）日：1996-12-03
• US5783679A
  申请人：——

  公开号：US5783679A

  公开（公告）日：1998-07-21
• [EN] PURINE NUCLEOSIDE MODIFICATIONS BY PALLADIUM CATALYZED METHODS<br/>[FR] MODIFICATIONS DE NUCLEOSIDES PURIQUES PAR DES PROCEDES DE CATALYSE AU PALLADIUM
  申请人：NEXSTAR PHARMACEUTICALS, INC.

  公开号：WO1996016972A1

  公开（公告）日：1996-06-06

  (EN) This invention discloses an improved method for the preparation of modified purine nucleosides using a palladium catalyst.(FR) L'invention concerne un procédé perfectionné permettant de préparer des nucléosides puriques modifiés au moyen d'un catalyseur à palladium.