CAS: 97845-60-8; 2-(2-(2-Amino-6-Chloro-9H-Purin-9-yl)Ethyl)Propane-1,3-Diyl Diacetate

该化合物是一种属于纯衍生物类的化学化合物.它有一个纯基,具体地说,是2-氨-6-6-氯-氯纯,它与丙烷基链相连,再用两种乙酸组替代.这一结构表明,该化合物可能表现出生物活动,有可能影响核酸代谢,或作为各种生物化学途径的抑制剂.氨基和氯基组的存在表明,它可能参与氢联结和其他相互作用,可能影响其溶性与再活性.二乙酸会增强其脂性,有可能影响其药用皮肤特性.

英文名称2-(2-(2-Amino-6-Chloro-9H-Purin-9-yl)Ethyl)Propane-1,3-Diyl Diacetate
中文名称9-(4-乙酰氧基-3-乙酰氧甲基丁基)-2-氨基-6-氯嘌呤
IUPAC名称2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate
其它别名1,3-Propanediol,2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-, diacetate (ester) (9CI); 9-(4-Acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine; 9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chl; 1,3-Propanediol,2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-, 1,3-diacetate
CAS编号97845-60-8
MFCD编号:MFCD08458206
EINECS号:619-293-7
FDA UNII编号:V9DM57H0B7
分子式:C14H18ClN5O4
分子量:355.78
产品CID: 2023172
产品分类生物化工 → 核苷类药物 → 核苷中间体

相似结构搜索
InChIKey: KXPSHSVVYGZKAV-UHFFFAOYSA-N
InChI=1S/C14H18ClN5O4/c1-8(21)23-5-10(6-24-9(2)22)3-4-20-7-17-11-12(15)18-14(16)19-13(11)20/h7,10H,3-6H2,1-2H3,(H2,16,18,19)…
计算化学: 氢键受体数8.0氢键供体数1.0可旋转键数9.0

MSDS等安全信息

GHS象形图
GHS符号GHS08;
注释: Health hazard
危险类别致突变性类别2
警示词Warning(警告)
危险描述H341 |怀疑导致遗传缺陷.
防范说明P264-P270-P301+P312-P330-P501
安全声明H303+H313+H333

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

172529-93-0 = 97845-60-8
反应条件:1.1 Reagents: Sodium Borohydride Solvents: Dichloromethane1.2 Reagents: Triethylamine,4-(Dimethylamino)Pyridine Solvents: Dichloromethane1.1 Reagents: Sodium Borohydride Solvents: Dichloromethane; 20 Min,20 °C1.2 Reagents: Methanol; 20 °C; 2 H,25 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 6.81.4 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)Pyridine Solvents: 1,2-Dichloroethane; 20 Min,Rt1.5 Reflux; 2 H,Reflux; Reflux -> 20 °C; < 20 °C1.6 Reagents: Sodium Hydroxide Solvents: Water; Ph 6.81.1 Reagents: Sodium Borohydride Solvents: Methanol,Dichloromethane; 20 °C; 20 H,20 - 22 °C; 90 Min,20 - 22 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 20 - 22 °C; Ph 6 - 7,20 - 22 °C1.3 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 20 - 30 Min,Reflux; 90 Min,Reflux; Reflux -> 20 °C1.4 Reagents: Sodium Hydroxide Solvents: Water; Neutralized
标题:Preparation Of Antiviral Purine Derivativesimproved Synthesis Of Penciclovirmethod For Manufacturing Of Antiviral Agents Derived From Purine Compounds
作者:Deng,Yan; Et Al
参考文献:World Intellectual Property Organization 日期:2009 卷标:26(9) 页码:737-739]

333335-55-0 = 97845-60-8
反应条件:1.1 Reagents: Diisobutylaluminum Hydride Solvents: Tetrahydrofuran1.2 Reagents: Triethylamine,4-(Dimethylamino)Pyridine Solvents: Dichloromethane
标题:Regioselective Alkylation Of Guanines Using 2-Acetoxytetrahydrofurans
作者:Geen,G. R.; Et Al
参考文献:Tetrahedron Letters 日期:2001 卷标:42(9) 页码:1781-1784]

172529-94-1 = 97845-60-8
反应条件:1.1 Catalysts: Triethylamine,4-(Dimethylamino)Pyridine Solvents: Dichloromethane; Reflux; 1 H,Reflux; Reflux -> Rt1.2 Reagents: Sodium Hydroxide Solvents: Water; Ph 6.5,Rt1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 25 - 35 °C; 35 °C -> 45 °C; 3 H,45 °C1.1 Reagents: Triethylamine Solvents: Dichloromethane; 1 H,Heated; Ph 7,Rt
标题:Synthesis Of Famciclovirimproved Process For Preparation Of Penciclovir And Intermediates Thereofsynthesis And Structural Elucidation Of Famciclovir
作者:Chen,Wen-Hun Rani,B. Sudha; Et Al
参考文献:Huaxue Shiji 日期:2006 卷标:28(3) 页码:185-186]

256945-18-3 = 97845-60-8
反应条件:1.1 Reagents: Tetrabutylammonium Chloride Solvents: Acetonitrile; Rt -> 0 °C1.2 Reagents: Triethylamine,Phosphorus Oxychloride; 1 H,80 °C1.3 Reagents: Sodium Hydroxide Solvents: Dichloromethane,Water; 0 °C1.4 Reagents: Sodium Bicarbonate Solvents: Water; 0.5 H,Rt1.5 Solvents: Methanol; 25 H,15 °C; Ph 11.6 Reagents: Sodium Bicarbonate Solvents: Water; Ph 1 -> Ph 7.0; 1.5 H,0 °C
标题:Practical Syntheses Of Penciclovir And Famciclovir From N2-Acetyl-7-Benzylguanine
作者:Torii,Takayoshi; Et Al
参考文献:Tetrahedron 日期:2006 卷标:62(24) 页码:5709-5716]

10310-21-1 + 127047-77-2 = 97845-60-8
反应条件:1.1 Reagents: Potassium Carbonate Solvents: Dimethylformamide1.1 Reagents: Potassium Carbonate Solvents: Dimethylformamide; 16 H,Rt
标题:The Effect Of The C-6 Substituent On The Regioselectivity Of N-Alkylation Of 2-Aminopurinessynthesis Of Penciclovir
作者:Geen,Graham R.; Et Al Chen,Meiling; Et Al
参考文献:Tetrahedron 日期:1990 卷标:46(19) 页码:6903-14]

97845-72-2 = 97845-60-8
反应条件:1.1 Reagents: Tetrabutylammonium Chloride Solvents: Acetonitrile; Rt -> 0 °C1.2 Reagents: N,N-Dimethylaniline,Phosphorus Oxychloride; 1 H,70 °C1.3 Reagents: Sodium Bicarbonate Solvents: Dichloromethane,Water; Rt1.4 Solvents: Methanol,Water; 1.5 H,-5 °C1.1 Reagents: Benzyltriethylammonium Chloride,N,N-Dimethylaniline,Phosphorus Oxychloride Solvents: Acetonitrile; 0 °C; 1.5 H,70 °C1.2 Solvents: Methanol,Water; 1.5 H,0 °C
标题:Practical Syntheses Of Penciclovir And Famciclovir From N2-Acetyl-7-Benzylguaninevirtual Screening Of Acyclovir Derivatives As Potential Antiviral Agents: Design,Synthesis,And Biological Evaluation Of New Acyclic Nucleoside Protides
作者:Torii,Takayoshi; Et Al Derudas,Marco; Et Al
参考文献:Tetrahedron 日期:2006 卷标:62(24) 页码:5709-5716]

122497-17-0 = 97845-60-8
反应条件:1.1 Reagents: Sodium Borohydride Solvents: Dichloromethane; 20 °C1.2 Reagents: Methanol; 2 H,20 - 22 °C; 1.5 H,20 - 22 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 6.7 - 7,20 - 22 °C1.4 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 20 - 30 Min,Reflux; 1.5 H,Reflux; Reflux -> 20 °C1.5 Reagents: Sodium Hydroxide Solvents: Water; Ph 6.4 - 6.5
标题:An Improved And Commercially Viable Process For The Preparation Of Famciclovir
参考文献:India

鸟苷置于palladium On Activated Charcoal 盐酸,4-二甲氨基吡啶,四乙基氯化铵,氢气,Sodium Acetate,Potassium Carbonate,对甲苯磺酸,溶剂黄146,N,N-二甲基苯胺,Sodium Bromide,三氯氧磷体系中,用 N-甲基吡咯烷酮,甲醇,水,N,N-二甲基甲酰胺,乙腈作为反应溶剂,40.0~105.0 °C,101.33 Kpa 条件下,反应 59.0H,反应生成 9-(4-乙酰氧基-3-乙酰氧甲基丁基)-2-氨基-6-氯嘌呤
参考文献:Practical Syntheses Of Penciclovir And Famciclovir From N2-Acetyl-7-Benzylguanine
标题:Practical Syntheses Of Penciclovir And Famciclovir From N2-Acetyl-7-Benzylguanine
摘要:We Have Established Practical Methods For The Synthesis Of Penciclovir (Pcv) And Famciclovir (Fcv) From Readily Available Guanosine Via N2-Acetyl-7-Benzylguanine. The Alkylation Of N2-Acetyl-7-Benzylguanine Proceeded Selectively At The N9 Position To Give The Desired Alkylated Product In Good Yield In Salt Form. After Conventional Catalytic Hydrogenolysis Of The Benzyl Group And Hydrolysis Of The Resulting Acetate,Pure Pcv Was Obtained Without The Need For Chromatography. As A Side Chain Precursor,The Mesylate Was Selected Rather Than A Halide Since The Corresponding Halides Gave Several Impurities Under The Same Reaction Conditions. Two Procedures For The Synthesis Of Fcv From Pcv And A Derivative Are Also Reported. (C) 2006 Elsevier Ltd. All Rights Reserved.
DOI:10.1016/j.Tet.2006.03.080

海关参考信息

2905121000-正丙醇
2905399001-1,3-丙二醇
2909110000-乙醚
2912110000-甲醛
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专利信息

专利号:US-6388074-B2
优先权日:1983-08-18
标题 :Process for the preparation of purine derivatives
发明人：GEEN GRAHAM RICHARD; JARVEST RICHARD LEWIS
权利人:NOVARTIS INT PHARM LTD
摘要:The present invention provides a process for the synthesis of penciclovir and famciclovir by 9-substituting 2-amino-6-chloropurine (ACP) with an appropriate side chain precursor, followed by conversion of the 6-chloro moiety to a hydroxy moiety (i.e. to form a guanine) or hydrogen (to form a 2-aminopurine), respectively.