8-bromo-9-[(2R,4S,5R)-4-trimethylsilyloxy-5-(trimethylsilyloxymethyl)oxolan-2-yl]purin-6-amine | 913069-30-4

• 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: 8-bromo-9-[(2R,4S,5R)-4-trimethylsilyloxy-5-(trimethylsilyloxymethyl)oxolan-2-yl]purin-6-amine
• CAS: 913069-30-4
• 化学式: C₁₆H₂₈BrN₅O₃Si₂
• 分子量: 474.505
• InChiKey: SNZCTOWYROPAAS-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  97.31
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  8-bromo-9-[(2R,4S,5R)-4-trimethylsilyloxy-5-(trimethylsilyloxymethyl)oxolan-2-yl]purin-6-amine 在 N-甲基吡咯烷酮 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 2'-deoxy-8-ethyladenosine
  参考文献：
  名称：

  通过与四烷基锡试剂交叉偶联获得的C-烷基化嘌呤核苷的抗病毒活性。

  摘要：

  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。

  DOI：

  10.1021/jm00072a013
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 氢溴酸 、 sodium acetate 作用下， 反应 0.5h， 生成 8-bromo-9-[(2R,4S,5R)-4-trimethylsilyloxy-5-(trimethylsilyloxymethyl)oxolan-2-yl]purin-6-amine
  参考文献：
  名称：

  Synthesis of photoactive DNA: incorporation of 8-bromo-2′-deoxyadenosine into synthetic oligodeoxynucleotides

  摘要：

  8-Bromo-N6-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine-3'-O-(2-cyanoethyl-N,N-diisopropyl) phosphoramidite was synthesized and used to introduce 8-bromo-2'-deoxyadenosine (8-Br-dA) into oligodeoxynucleotides by means of automated synthesis. 8-Br-dA was found not to affect adversely the stability of duplex DNA, as judged by the melting behavior of several 8-Br-dA-containing duplexes.

  DOI：

  10.1016/s0040-4039(00)74234-1

文献信息

• Effects of 8-methyl-2′-deoxyadenosine incorporation into quadruplex forming oligodeoxyribonucleotides
  作者：Antonella Virgilio、Veronica Esposito、Antonio Randazzo、Luciano Mayol、Aldo Galeone

  DOI：10.1016/j.bmc.2004.11.037

  日期：2005.2

  In this paper we report the synthesis and the structural characterization of two modified oligodeoxyribonucleotides (ODNs), namely d(A(8Me)GGGT) and d(TA(8Me)GGGT), where A(8Me) represents a 8-methyl-2'-deoxyadenosine. Both ODNs have been studied by H-1 NMR, CD spectroscopy and molecular modelling and shown to form fourfolds symmetric G-quadruplex structures, with all strands parallel and equivalent to each other. The complexes are characterized by thermal stabilities comparable to that of their natural counterparts. NOE patterns involving 8-methyl group in A(8Me) residues allowed us to define the main structural features at 8 the 5'-end of the complexes. Particularly, inter- and intrastrand NOEs show a syn-orientation and a symmetrical arrangement of A(8Me) bases stacking on the adjacent G-tetrad. (C) 2004 Elsevier Ltd. All rights reserved.