CAS: 102728-64-3; 2-((2-Amino-6-Oxo-1H-Purin-9(6H)-yl)Methoxy)Ethyl Acetate

该化合物是一种合成核素类比,显示对guanine基的结构性改变;该化合物的特点是在抗生素结构的9个位置上存在一种乙氧氧基甲基组,这提高了其溶性性和生物利用率;乙氧基组的存在可能影响其与生物目标的相互作用,有可能影响其药理特性;作为核素的类同,它可能通过干扰核酸合成或功能而表现出抗病毒或抗癌活动;该复合的特性包括其分子重量,各种溶剂的溶性以及生理条件下的稳定性,这些对于其在药用化学中的应用至关重要;此外,其合成和特征涉及标准的有机化学技术,其生物活动可以通过各种分析来评估,以确定其功效和安全性;总体而言,9-(2)-乙氧乙氧甲基基氧基氮基甲酸)九guaine是药物发展和分子生物学研究的一个重要领域.

结构式图片

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2-amino-1,9-dihydro-6H-purin-6-one 2-acetoxyethyl acetoxymethyl ether 1,1,1,3,3,3-hexamethyl-disilazane 6-Trimethylsilanyloxy-9H-purin-2-ylamine acycloguanosine -2-amino-6-chloro-9H-purine9-(2-acetoxyethoxy)methyl-2-amino-6-chloro-9H-purine valacyclovir Hydr°Chloride 2-[(2-amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy]ethyl N-[(benzyloxy)carbonyl]-L-valinate

合成工艺路线路线简述

  • 合成目标产物 9-(2'-Acetoxyethoxymethyl)-Guanine 主要起始原料 Guanine And 2-[(Acetyloxy)Methoxy]Ethyl Acetate
  • (文献来源)合成步骤主要原料 Guanine 和 2-[(Acetyloxy)Methoxy]Ethyl Acetate
鸟嘌呤置于cesium Iodide Ammonium Sulfate体系中,用 乙腈 用作溶剂,化学反应 3.0H,反应生成9-(2-乙酰氧基乙氧基甲基)鸟嘌呤
参考文献:Efficient Synthesis Of Acyclic Nucleosides By N-Alkylation Of Pyrimidine And Purine-Bases Using A New Coupling Agent Of Cesium Iodide
标题:Efficient Synthesis Of Acyclic Nucleosides By N-Alkylation Of Pyrimidine And Purine-Bases Using A New Coupling Agent Of Cesium Iodide
摘要:成功合成了无环核苷,包括((1,3-双(苄氧基)-2-丙氧基)甲基)-2-硫代吡啶,-尿嘧啶,-2-硫代尿嘧啶和-2-硫代腺嘌呤,以及(2-乙酰氧乙氧基甲基)-2-硫代腺嘌呤,-2-硫代吡啶,-尿嘧啶和-2-硫代尿嘧啶,合成方法为在中性条件下,使用碘化铯在乙腈中通过与相应的烷基乙酸酯(2)和烷基氯化物(3)进行n-烷基化反应,获得了非常好的产量.
Doi:10.1246/cl.1988.1045

专利信息


专利号:US-5496945-A
优先权日:1993-06-14
标题 :Process for the synthesis of 9-(2-hydroxyethoxy methyl) guanine
发明人:BRUZZESE TIBERIO; GUAZZI GIUSEPPE; ROGNONI MARCO; MARCON GIULIANO
权利人:SOLAR CHEM SA
摘要:A process for the synthesis of 9-(2-hydroxyethoxy methyl) guanine in which guanine, or its salts, is reacted with 2-4 moles of hexamethyldisilazane, in the presence of an aprotic solvent and of ammonium sulfate. Thereafter, the trimethylsilyl derivative, without being isolated, is reacted with a stoichiometric quantity of an acyloxyethoxy methyl halide and hydrolyzed with aqueous sodium acetate or sodium hydroxyde to give 9-(2-hydroxyethyoxy methyl) guanine.

专利号:US-5648489-A
优先权日:1994-05-17
标题 :Syntheses of acyclic guanine nucleosides
发明人:CHU CHUNG K; DU JINFA; WANG CHUNGUANG
权利人:UNIV GEORGIA
摘要:A method is provided for the synthesis of synthesis of acyclic purine nucleosides, particularly 9-(2-hydroxy-ethoxymethyl)-guanine (acyclovir) and 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine ('DHPG') where the N2,N9-diprotected guanine is reacted with CH3C(O)OCH2O(CH2)2)OC(O)CH3 or 2-acetoxymethoxy-1,3-diacetoxypropane, respectively, in the presence of a mixture of an acid and acetic anhydride, or in the presence of an acid, where the acid can be phosphoric acid or polyphosphoric acid.

专利号:WO-9941229-A1
优先权日:1998-02-11
标题:Halogenated phenyl alcohol amides (ligands of gabab receptor) having an anticonvulsant activity
发明人:CARVAJAL SANDOVAL GUILLERMO; MEZA TOLEDO SERGIO ENRIQUE
权利人:CARVAJAL SANDOVAL GUILLERMO; MEZA TOLEDO SERGIO ENRIQUE
摘要:New anticonvulsant compounds have been synthesized with a chlorine or fluorine atom in the position para of the phenyl ring. These compounds include DL-2-hydroxy-2-(4'-chlorophenyl)butyramide, DL-2-hydroxy-2-(4'-fluorophenyl)butyramide, DL-3-hydroxy-3-(4'-chlorophenyl)pentanamide, DL-3-hydroxy-3-(4'-fluorophenyl)pentanamide, DL-4-hydroxy-4-(4'-chlorophenyl)hexanamide and DL-4-hydroxy-4-(4'-fluorophenyl)hexanamide. Said compounds have a rather significant anticonvulsant activity against convulsions produced by pentylene tetrazol, as well as unexpected properties in particular a high affinity to the GABAB receptor in addition to a sustained anticonvulsant activity. The invention also relates to methods for the synthesis of halogenated phenyl alcohol amides such as indicated in the examples given in the disclosure.

专利号:US-5565565-A
优先权日:1994-08-04
标题 :Preparation of N-9 substituted guanine compounds
发明人:LODEWIJK ERIC; HAN YEUN-KWEI; SCHLOEMER GEORGE C; NGUYEN SAM L
权利人:SYNTEX INC
摘要:The invention relates to efficient and selective processes for the synthesis of the antiviral N-9 substituted guanine compounds acyclovir and ganciclovir.

专利号:RU-2111967-C1
优先权日:1996-09-26
标题:Method of synthesis of aciclovir

专利号:DE-69409578-T2
优先权日:1993-06-14
标 题:Process for the synthesis of 9- (2-hydroxyethoxymethyl) guanine
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合成参考文献


参考文献:10.1021/jm0308747
摘要:Prekupec S, Svedruzić D, Gazivoda T, Mrvos-Sermek D, Nagl A, Grdisa M, Pavelić K, Balzarini J, De Clercq E, Folkers G, Scapozza L, Mintas M, Raić-Malić S. Synthesis and biological evaluation of iodinated and fluorinated 9-(2-hydroxypropyl) and 9-(2-hydroxyethoxy)methyl purine nucleoside analogues. J Med Chem. 2003 Dec 18;46(26):5763–72. doi: 10.1021/jm0308747.
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