2'-脱氧-8-(苯基甲氧基)-鸟苷 | 96964-90-8

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 2'-脱氧-8-(苯基甲氧基)-鸟苷
• 中文别名: 1-苯并噻庚英-5(2H)-酮,4-氨基-3,4-二氢-7-甲基-
• 英文名称: 8-benzyloxy-2'-deoxyguanosine
• 英文别名: 8-Benzyloxy-2'-deoxyguanosine；2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-phenylmethoxy-1H-purin-6-one
• CAS: 96964-90-8
• 化学式: C₁₇H₁₉N₅O₅
• 分子量: 373.368
• InChiKey: AMEUNRVTNJBDJN-QJPTWQEYSA-N

物化性质

• 熔点：
  175-177°C
• 密度：
  1.70±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  7

制备方法与用途

2′-脱氧-8-(苯基甲氧基)鸟苷是一种嘌呤核苷类似物，具有广泛的抗肿瘤活性，特别是针对惰性淋巴系统恶性肿瘤。其抗癌机制主要通过抑制DNA合成和诱导细胞凋亡来实现。

反应信息

• 作为反应物：
  描述：

  2'-脱氧-8-(苯基甲氧基)-鸟苷 在 吡啶 、 咪唑 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 N-[9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-methoxy-8-phenylmethoxypurin-2-yl]-2-phenoxyacetamide
  参考文献：
  名称：

  8-oxo-7,8-dihydro-6- O -methyl-2'-deoxyguanosine的合成及其作为研究MutY酶DNA碱基切除的探针的用途

  摘要：

  由2'-脱氧鸟苷合成了含有8-氧代-7,8-二氢-6- O-甲基-2'-脱氧鸟苷（1）的23mer低聚物。已经研究了MutY蛋白对此的活性以及相关的包含8-甲氧基-dG的寡聚物。

  DOI：

  10.1016/0040-4039(95)02069-1
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 N-溴代丁二酰亚胺(NBS) 、 sodium 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 2'-脱氧-8-(苯基甲氧基)-鸟苷
  参考文献：
  名称：

  8-oxo-dGTP 及其 β,γ-CH2-、β,γ-CHF- 和 β,γ-CF2- 类似物的合成

  摘要：

  已经由8 - oxo - dGMP 2通过它的吗啉 5'-氨基磷酸酯14或优选地，它的N-甲基咪唑 5'-氨基磷酸酯15与适当的双膦酸的三正丁基铵盐11-13。后一种方法还提供了一个方便的新途径3。类似物4 – 6可能可用作3在异常DNA复制和修复中的作用的机械探针。

  DOI：

  10.1016/j.tetlet.2021.152890

文献信息

• Methods of screening for nucleoside analogs that are incorporated by HIV
  申请人：Darwin Molecular Corporation

  公开号：US05512431A1

  公开（公告）日：1996-04-30

  Methods and compositions related to HIV are disclosed. Using the methods of the present invention, nucleoside analogs may be screened for the ability to be incorporated by reverse transcriptase of human immunodeficiency virus ("HIV RT") and cause incorrect base pairing. Progressive mutation of the virus by such nucleoside analogs renders it non-viable.

  本发明揭示了与HIV相关的方法和组合物。使用本发明的方法，可以筛选核苷类似物，以确定其是否能够被人类免疫缺陷病毒（“HIV RT”）的反转录酶所合并，并引起不正确的碱基配对。通过这些核苷类似物对病毒的逐步突变使其无法生存。
• METHODS AND COMPOSITIONS RELATED TO MODIFIED GUANINE BASES FOR CONTROLLING OFF-TARGET EFFECTS IN RNA INTERFERENCE
  申请人：Burrows Cynthia J.

  公开号：US20120095077A1

  公开（公告）日：2012-04-19

  Disclosed are compositions and methods related to modified nucleobases. Also disclosed are compositions and methods related to modified interfering RNAs. Also disclosed are compositions and methods related to modified guanine bases for controlling off-target effects in RNA interference.

  本发明涉及修饰核苷酸的组合物和方法。还涉及修饰干扰RNA的组合物和方法。还涉及修饰鸟嘌呤碱基以控制RNA干扰中的非特异性效应的组合物和方法。
• Methods of screening for nucleoside analogs that are incorporated by HIV reverse transcriptase and cause incorrect base pairing
  申请人：DARWIN MOLECULAR CORPORATION

  公开号：EP1004675A2

  公开（公告）日：2000-05-31

  Methods and compositions related to HIV are disclosed. Using the methods of the present invention, nucleoside analogs may be screened for the ability to be incorporated by reverse transcriptase of human immunodeficiency virus ("HIV RT") and cause incorrect base pairing. Progressive mutation of the virus by such nucleoside analogs renders it non-viable.

  本发明公开了与艾滋病毒有关的方法和组合物。使用本发明的方法，可以筛选出核苷类似物，以确定其是否能被人类免疫缺陷病毒（"HIV RT"）的逆转录酶结合，并导致不正确的碱基配对。这种核苷类似物可使病毒发生渐进变异，从而使其丧失生存能力。
• Synthesis of <i>N</i>²-Alkyl-8-oxo-7,8-dihydro-2′-deoxyguanosine Derivatives and Effects of These Modifications on RNA Duplex Stability
  作者：Arunkumar Kannan、Cynthia J. Burrows

  DOI：10.1021/jo102187y

  日期：2011.1.21

  N-2-Alkyl analogues of 8-oxo-7,8-dihydro-2'-deoxyguanosine (OG) were synthesized (alkyl = propyl, benzyl) via reductive amination of the protected OG nucleoside and incorporated into various positions of an RNA strand. Thermal stability studies of duplexes containing A or C opposite a single modified base revealed only moderate destabilization. Both OG as well as its N-2-alkyl analogues can pair opposite A or C with nearly equal stability, potentially offering a new means of modulating RNA protein interactions in the minor vs major grooves.
• 8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells
  作者：Tai Shun Lin、Jia Chong Cheng、Kimiko Ishiguro、Alan C. Sartorelli

  DOI：10.1021/jm00147a012

  日期：1985.9

  A variety of 8-substituted guanosine and 2'-deoxyguanosine derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells in culture. The most active agents in the guanosine series were 8-substituted-N(CH3)2, -NHCH3, -NH2, -OH, and -SO2CH3, which caused 68, 42, 34, 33, and 30% of erythroleukemia cells to attain benzidine positivity, a functional measure of maturation, at concentrations of 5, 1, 0.4, 5, and 5 mM, respectively. The 8-OH derivative of the 2'-deoxyguanosine series produced comparable activity, causing 62% benzidine-positive cells at a level of 0.2 mM. These findings indicate that 8-substituted analogues of guanosine and 2'-deoxyguanosine have the potential to terminate leukemia cell proliferation through conversion to end-stage differentiated cells.