CAS: 96964-90-8; 2′-Deoxy-8-(Phenylmethoxy)Guanosine

该化合物是一种纯衍生物,其结构复杂,包括氨基组,苯氧基替代体和四氢氟基丁酸.这种化合物具有双环净核心特征,对生物活动至关重要,特别是在核酸化学领域.水氧甲基组和四氢氟呋喃的存在有助于其溶性以及与生物目标的潜在互动.其结构特征表明,它可能具有与药用化学有关的特性,可能在生物化学途径中起到抑制或调节作用.根据(2R,5R)配置,化合物的立体化学对其生物活动至关重要,影响它与酶或受体相互作用的方式.

英文名称2′-Deoxy-8-(Phenylmethoxy)Guanosine
中文名称2'-脱氧-8-(苯基甲氧基)-鸟苷
IUPAC名称2-amino-8-(benzyloxy)-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one
其它别名8-Benzyloxy-2'-Deoxyguanosine
CAS编号96964-90-8
MFCD编号:MFCD03701133
分子式:C17H19N5O5分子量:373.37
产品CID: 2019594
产品分类医药中间体 → 原料药中间体

相似结构搜索
InChIKey: AMEUNRVTNJBDJN-PQDIPPBSSA-N
InChI=1S/C17H19N5O5/c18-16-20-14-13(15(25)21-16)19-17(26-8-9-4-2-1-3-5-9)22(14)12-6-10(24)11(7-23)27-12/h1-5,10-12,23-24H,6-8H2,(H3,18,20,21,25)/t10-,11+,12+/m0/s1
计算化学: 氢键受体数7.0氢键供体数4.0可旋转键数5.0

物理性质

熔点175-177°C
沸点175-177 °C
密度1.70±0.1 g/cm3(预测)
pKa:9.30±0.20(预测)
PSA:148.51
LogP:0.5027
折射率1.772
溶解性DMSO (Slightly), Methanol (Slightly)
外观形态浅米色至棕色固体
产品应用该化合物是针对同性淋巴瘤恶性肿瘤的活动;它的抗癌机制包括抑制DNA合成和诱导流行性硬化.

MSDS等安全信息

警示词warning
危险描述H303 May be harmful if swallowed+H313 Skin contact may be harmful+H333 Inhalation may be harmful to the body
防范说明P264+P280+P305+P351+P338+P337+P313
安全声明H303+H313+H333

上下游产品

8-bromo-2'-deoxyguanosine benzyl alcohol sodium phenyl-methanolate dimethyl sulfoxide 7,8-dihydro-8-oxo-2'-deoxyguanosine 2-Amino-8-benzyloxy-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one 2'-deoxy-7,8-dihydro-8-oxoguanosine-5'-triphosphate 7,8-dihydro-8-oxo-2'-deoxyguanosine

合成工艺路线路线简述

合成目标产物 8-Benzyloxy-2'-Deoxy-D-Guanosine 主要起始原料 8-Bromo-2'-Deoxyguanosine And Benzyl Alcohol
100-51-6 + 13389-03-2 = 96964-90-8
反应条件:1.1 Reagents: Sodium Solvents: Dimethyl Sulfoxide
标题:Efficient Synthesis Of 8-Oxo-Dgtp: A Mutagenic Nucleotide
作者:Nampalli,S.; Kumar,S.
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2000 卷标:10(15) 页码:1677-1679]

100-51-6 + 13389-03-2 = 96964-90-8
反应条件:1.1 Reagents: Sodium Solvents: Dimethyl Sulfoxide,Dimethylformamide; Overnight,70 °C
标题:Synthesis Of 8-Oxo-Dgtp And Its β,γ-Ch2-,β,γ-Chf-,And β,γ-Cf2- Analogues
作者:Zheng,Yiying; Haratipour,Pouya; Kashemirov,Boris A.; Mckenna,Charles E.
参考文献:Tetrahedron Letters 日期:2021 卷标:67]

= 96964-90-8 [标题:Reaction Conditions
标题:8-Substituted Guanosine And 2'-Deoxyguanosine Derivatives As Potential Inducers Of The Differentiation Of Friend Erythroleukemia Cells
作者:Lin,Tai Shun; Cheng,Jia Chong; Ishiguro,Kimiko; Sartorelli,Alan C.
参考文献:Journal Of Medicinal Chemistry 日期:1985 卷标:28(9) 页码:1194-8]

100-51-6 + 13389-03-2 = 96964-90-8
反应条件:1.1 Reagents: Sodium Solvents: Dimethyl Sulfoxide
标题:Synthesis And Thermodynamic Studies Of Oligodeoxyribonucleotides Containing Tandem Lesions Of Thymidine Glycol And 8-Oxo-2'-Deoxyguanosine
作者:Wang,Yuesong; Wang,Yinsheng
参考文献:Chemical Research In Toxicology 日期:2006 卷标:19(6) 页码:837-843]

100-51-6 + 13389-03-2 = 96964-90-8
反应条件:1.1 Reagents: Sodium; 60 °C1.2 Solvents: Dimethyl Sulfoxide; 24 H,65 °C
标题:Blocking Protein Binding Of Small Interfering Rnas With Guanine Analogs Filling The Major Groove To Prevent Off-Target Effects
参考文献:World Intellectual Property Organization]

13389-03-2 + 20194-18-7 = 96964-90-8
反应条件:1.1 Solvents: Dimethyl Sulfoxide,Benzyl Alcohol
标题:Synthesis Of 8-Oxo-7,8-Dihydro-6-O-Methyl-2'-Deoxyguanosine And Its Use As A Probe To Study Dna-Base Excision By Muty Enzyme
作者:Varaprasad,Chamakura V.; Bulychev,Nickolai; Grollman,Arthur P.; Johnson,Francis
参考文献:Tetrahedron Letters 日期:1996 卷标:37(1) 页码:9-12]

= 96964-90-8 [标题:Reaction Conditions
标题:A Serendipitous Synthesis Of 8-Dimsyl-2'-Deoxyguanosine
作者:Nampalli,Satyam; Livshin,Inna; Kumar,Shiv
参考文献:Nucleosides & Nucleotides 日期:1999 页码:697-699

📜2'-脱氧鸟苷置于n-溴代丁二酰亚胺(Nbs),Sodium体系中,用水,乙腈作为反应溶剂,化学反应 1.0H,反应生成 2'-脱氧-8-(苯基甲氧基)-鸟苷
参考文献:8-Oxo-Dgtp 及其 β,γ-Ch2-,β,γ-Chf-和 β,γ-Cf2-类似物的合成
标题: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