N-(4-丁基苯基)-2'-脱氧鸟苷 | 87781-96-2

• 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: N-(4-丁基苯基)-2'-脱氧鸟苷
• 中文别名: 环戊甲酰胺,1-氨基-2-(1-甲基乙基)-,(1S,2R)-
• 英文名称: N2-(p-n-Butylphenyl)-9-(2-deoxy-β-D-ribofuranosyl)guanine
• 英文别名: N(2)-(4-n-Butylphenyl) 2'-deoxyguanosine；2-(4-butylanilino)-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 87781-96-2
• 化学式: C₂₀H₂₅N₅O₄
• 分子量: 399.45
• InChiKey: HPXCEMUJBTUFGO-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-丁基苯基)-2'-脱氧鸟苷 在 吡啶 、 四丁基氢氧化铵 作用下， 反应 0.5h， 生成 N2-(4-n-Butylphenyl)-2'deoxy-3,5'-cycloguanosine
  参考文献：
  名称：

  Synthesis of the P¹, P²-Methylene Analog of N²- (p-n-Butylphenyl)-2′- deoxyguanosine 5′-Triphosphate: A Non-substrate Inhibitor of DNA Polymerases

  摘要：

  N-2-(p-n-Butylphenyl)-2'-deoxyguanosine 5'-(P-1,P-2-methylene)-triphosphate (BuPdGMPCH(2)PP) has been synthesized. Displacement of the mesyloxy group of 5'-MesBuPdG by methanediphosphonate gave 30% of BuPdGMPCH(2)P, but 68% of 3,5'-cycloBuPdG. Reaction of the nucleoside BuPdG with methanediphosphonate and DCC gave 62% of BuPdGMPCH(2)PPCH(2)P, which was hydrolyzed to BuPdGMPCH(2)P in 77% yield. The title compound was obtained by reacting the imidazolide of BuPdGMPCH(2)P with orthophosphate. BuPdGMPCH(2)PP inhibited calf thymus DNA polymerase a with K-i = 9.5 nM, a potency only fivefold weaker than that of BuPdGTP itself.

  DOI：

  10.1080/15257779408013245
• 作为产物：
  描述：

  2-溴次黄嘌呤 在 sodium methylate 、 sodium hydride 、 4-丁基苯铵氯化物 、 N,N-二甲基苯胺 、 2-巯基乙醇 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 乙二醇甲醚 为溶剂， 反应 97.5h， 生成 N-(4-丁基苯基)-2'-脱氧鸟苷
  参考文献：
  名称：

  2-（pn-丁基苯胺基）嘌呤及其核苷类似物的合成，细胞生长抑制和抗肿瘤筛选。

  摘要：

  合成了N2-（pn-丁基苯基）鸟嘌呤（BuPG）和2-（pn-丁基苯胺基）腺嘌呤（BuAA）的衍生物，并测试了它们作为哺乳动物DNA聚合酶α，细胞生长和大分子合成的抑制剂。2-（pn-Butylanilino）-6-氯嘌呤（BuACl）用作制备一系列6取代类似物的有用中间体。BuACl的钠盐与2-乙氧基3,5-二-对甲苯甲酰基-β-D-呋喃呋喃糖基氯在乙腈中反应，得到64％的相应9-β核苷（封端的BuAdCl）和仅14％ 7-β异构体 在BuAdCl中对氯进行解封和取代生成了一系列2-（pn-丁基苯胺基）-9-（2-脱氧-β-D-核呋喃糖基）嘌呤衍生物。解封并取代6-氯基团后，BuACl的钠盐与（2-乙酰氧基乙氧基）甲基溴反应，一系列的2-（pn-丁基苯胺基）-9-[（2-羟基乙氧基）甲基]嘌呤。合成的碱基是从中国仓鼠卵巢细胞中分离的DNA聚合酶α的抑制剂，最有效的化合物是2-（pn-丁基

  DOI：

  10.1021/jm00384a019

文献信息

• Synthesis and characterization of N2-(p-n-butylphenyl)-2'-deoxyguanosine and its 5'-triphosphate and their inhibition of HeLa DNA polymerase .alpha.
  作者：George E. Wright、Lech W. Dudycz

  DOI：10.1021/jm00368a012

  日期：1984.2

  N2-(p-n-Butylphenyl)-2'-deoxyguanosine (BuPdG) and its 5'-triphosphate (BuPdGTP), expected to be inhibitors of eukaryotic DNA polymerase alpha, have been synthesized. BuPdG was synthesized by two methods and characterized by 1H NMR and by chemical relation to guanosine. Direct synthesis involving silylated N2-(p-n-butylphenyl)guanine (BuPG) and 1-chloro-3,5-di-p-toluoyl-2-deoxyribofuranose in the presence

  已经合成了N2-（pn-丁基苯基）-2'-脱氧鸟苷（BuPdG）及其5'-三磷酸（BuPdGTP），它们有望成为真核DNA聚合酶α的抑制剂。通过两种方法合成BuPdG，并通过1H NMR和与鸟嘌呤的化学关系进行表征。在三甲基甲硅烷基三氟甲磺酸酯存在下，直接合成包括甲硅烷基化的N2-（pn-丁基苯基）鸟嘌呤（BuPG）和1-氯-3,5-二-对甲苯甲酰基-2-脱氧核糖呋喃糖的方法得到了一个脱氧核糖核苷的α和两个β异构体通过1 H NMR。但是，NMR和UV光谱在区分7个和9个异构体方面是模棱两可的。所需的9-β-BuPdG的身份最终由其从相应的核糖核苷的独立合成中证实。O'的1 H NMR谱 BuPG的乙酰化核糖核苷表现出O'乙酰化鸟苷的特征性模式，并且通过将O'乙酰化的2-溴代肌苷异构体与pn丁基苯胺和氨反应的产物联系起来，证明了它们的同一性：2-溴代肌苷鸟苷还产生了可疑的9-β-核糖核苷B
• Chemoselective arylation of 2′-deoxyguanosine at N-2 with organoiron complexes
  作者：Gerard A. Potter、Raymond McCague、Michael Jarman

  DOI：10.1039/c39920000637

  日期：——

  2′-Deoxyguanosine has been directly and chemoselectively arylated at the N2-amino function by treatment with tricarbonyl(η5-cyclohexadienylium)iron or tricarbonyl[η5-2-(n-butyl)cyclohexadienylium]iron cations, followed by decomplexation and dehydrogenation, providing a rapid route to N2-aryl-2′-deoxyguanosine nucleosides.

  通过使用三羰基（δ-5-环己二烯基）铁或三羰基[δ-5-2-（正丁基）环己二烯基]铁阳离子处理 2'²-脱氧鸟苷，然后进行脱氨化和脱氢反应，可直接并化学选择性地在 N2-氨基功能处芳基化，从而为 N2-芳基-2'²-脱氧鸟苷核苷提供了一条快速途径。
• Synthesis and Biochemical Study of N²-(<i>p</i>-n-Butylphenyl)-2′-deoxyguanosine 5′-(α,β-imido)triphosphate (BuPdGMPNHPP): A Non-Substrate Inhibitor of B Family DNA Polymerases
  作者：James M. Stattel、Ivan Yanachkov、George E. Wright

  DOI：10.1080/07328319808003483

  日期：1998.8

  BuPdGMPNHPP was synthesized and assayed as a non-incorporable inhibitor of B family DNA polymerases. The derivative was synthesized by preparation of the imidophosphorane of BuPdG followed by reaction with orthophosphate using the imidazolide method. BuPdGMPNHPP inhibited human DNA polymerase alpha and T4 DNA polymerase 10 and 3.5-times more potently than BuPdGTP, respectively, and was not a substrate for either enzyme. BuPdGMPNHPP acts as an active site affinity probe that could find use in co-crystallization trials of B family DNA polymerases.
• Synthesis of biologically active N2-amine adducts of 2′-deoxyguanosine
  作者：Radha R Bonala、Irina G Shishkina、Francis Johnson

  DOI：10.1016/s0040-4039(00)01196-5

  日期：2000.9

  Several biologically important N-2-adducts of 2'-deoxyguanosine (dG) that previously were difficultly accessible, have been synthesized directly by means of the Buchwald-Hartwig reaction. The reaction employed in each case involves the coupling of 2'-deoxy-2-bromoinosine with the appropriate amine. Deprotection in all cases gave good yields of the desired 2-alkylated or -arylated deoxynucleoside. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of the P¹, P²-Methylene Analog of N²- (<i>p</i>-n-Butylphenyl)-2′- deoxyguanosine 5′-Triphosphate: A Non-substrate Inhibitor of DNA Polymerases
  作者：Ivan Yanachkov、George E. Wright

  DOI：10.1080/15257779408013245

  日期：1994.3

  N-2-(p-n-Butylphenyl)-2'-deoxyguanosine 5'-(P-1,P-2-methylene)-triphosphate (BuPdGMPCH(2)PP) has been synthesized. Displacement of the mesyloxy group of 5'-MesBuPdG by methanediphosphonate gave 30% of BuPdGMPCH(2)P, but 68% of 3,5'-cycloBuPdG. Reaction of the nucleoside BuPdG with methanediphosphonate and DCC gave 62% of BuPdGMPCH(2)PPCH(2)P, which was hydrolyzed to BuPdGMPCH(2)P in 77% yield. The title compound was obtained by reacting the imidazolide of BuPdGMPCH(2)P with orthophosphate. BuPdGMPCH(2)PP inhibited calf thymus DNA polymerase a with K-i = 9.5 nM, a potency only fivefold weaker than that of BuPdGTP itself.