CAS: 932-52-5; 5-Aminopyrimidine-2,4(1H,3H)-Dione

该化合物是一种微米衍生物,一种类似尿素的类似物,其特点是在聚氨环的5个位置上存在一个氨基组,其分子式为C4H4N2O2,其分子重量相对较低,该化合物一般是白色到白晶状固体,水中溶解和各种有机溶剂,有利于其在生物化学应用中的使用. 5-Aminouracil因其在核酸代谢中所起的作用而闻名,并研究其潜在的治疗用途,特别是在抗病毒和抗癌研究方面.氨基组增强了其再活性,允许进行各种化学修改,使其成为医药化学中有价值的化合物.此外,由于存在氨基和碳基功能组,它可以参与氢的结合,影响其在生物系统中的相互作用.

英文名称5-Aminopyrimidine-2,4(1H,3H)-Dione
中文名称5-氨基尿嘧啶
IUPAC名称5-amino-1H-pyrimidine-2,4-dione
其它别名5-Amino-2,4-pyrimidinediol; 5-Amino-2,4-dihydroxypyrimidine
CAS编号932-52-5
MFCD编号:MFCD00006025
EINECS号:213-252-3
FDA UNII编号:R2O7EKY9G9
分子式:C4H5N3O2
分子量:127.1
产品CID: 1970868
产品分类医药中间体 → 嘧啶类化合物

相似结构搜索
产品信息参考;;;;
InChIKey: BISHACNKZIBDFM-UHFFFAOYSA-N
InChI=1S/C4H5N3O2/c5-2-1-6-4(9)7-3(2)8/h1H,5H2,(H2,6,7,8,9)…
计算化学: 氢键受体数3.0氢键供体数3.0可旋转键数0.0

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别急性毒性类别4(经口)
警示词Warning(警告)
危险描述H302 |吞咽有害.
防范说明P264-P270-P301+P312+P330-P501-P301+P310a-P321-P405-P501a
UN编号NONH for all modes of transport
危险品标志Xn
安全声明22-24/25-36-26
危险类别码22-36/37/38-20/21/22
WGK Germany3

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

5-nitrobarbituric acid 5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid 2,4-dihydroxy-5-bromopyrimidine 5-bromouracil H-pyrimidine-2,4-dione5-[bis-(2-hydroxy-ethyl)-amino]-1H-pyrimidine-2,4-dione N-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-benzamideN-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-benzamide 4-chloro-2-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylamino)-benzoic acid 5-(1-thioureido)uracil

合成工艺路线路线简述

合成目标产物 5-Aminouracil 主要起始原料 5-Nitrouracil
127726-93-6 = 932-52-5
反应条件:1.1 Reagents: Water Solvents: Ethanol,Water
标题:The Synthesis And Chlorination Of Some Pyrimidin-4-Ols Having 5-Nitrogen Functionality
作者:Harnden,Michael R.; Hurst,Derek T.
参考文献:Australian Journal Of Chemistry 日期:1990 卷标:43(1) 页码:47-53]

= 932-52-5
反应条件:1.1 Reagents: Zinc Chloride,Nickelate(2-),Tetrakis(Cyano-Kc)-,Potassium (1:2),(Sp-4-1)- Solvents: Water; Rt1.2 Rt; 1 W,Rt
标题:Vibrational Spectroscopic Study Of Two Dimensional Polymer Compounds Of 5-Aminouracil
作者:Bayrak,Celal; Secken,Nilgun
参考文献:Asian Journal Of Chemistry 日期:2014 卷标:26(8) 页码:2241-2245]

= 932-52-5 [标题:Reaction Conditions
标题:Synthesis,Reactivity,And Biological Activity Of 5-Aminouracil And Its Derivatives
作者:Shaker,Raafat Mohamed; Abd Elrady,Mohamed; Sadek,Kamal Usef
参考文献:Molecular Diversity 日期:2016 卷标:20(1) 页码:153-183]

= 932-52-5 [标题:Reaction Conditions
标题:Preparation And Physicochemical Properties Of Uracil Derivatives With Potential Biological Activity
作者:Pecorari,P.; Vampa,G.; Albasini,A.; Rinaldi,M.; Melegari,M.; Et Al
参考文献:Farmaco 日期:1988 卷标:43(4) 页码:311-18]

= 932-52-5 [标题:Reaction Conditions
标题:2,4-Bis(Substituted) 5-Nitropyrimidines Of Expected Diuretic Action
作者:El-Kerdawy,M. M.; Zayed,A. A.; Abou Hamid,M. M.
参考文献:Egyptian Journal Of Chemistry 日期:1987 卷标:29(2) 页码:247-51]

5536-30-1 = 932-52-5 + 494754-71-1
反应条件:1.1 Catalysts: Thymidine Phosphorylase Solvents: Water; 2 H,Ph 6.8,37 °C
标题:Commercial Manufacture Of Nucleoside Compound And Purification Of The Product
参考文献:Japan]

618392-05-5 = 932-52-5 + 578-95-0
反应条件:1.1 Reagents: Water; 24 H,Neutralized,90 °C
标题:5-(Acridin-9-Yl-Amino)Uracil - A Hydrolytically Labile Nucleobase Modification In Peptide Nucleic Acid
作者:Matarazzo,Augusto; Hudson,Robert H. E.
参考文献:Canadian Journal Of Chemistry 日期:2013 卷标:91(12) 页码:1202-1206]

= 932-52-5
反应条件:1.1 Reagents: Sodium Bicarbonate,Sodium Dithionite Solvents: Water; 4 H,75 °C
标题:Process For Preparing 3,6-Diaminopyrazine-2,5-Dicarboxylic Acid And Synthetic Intermediate Thereof
参考文献:World Intellectual Property Organization]

= 932-52-5
反应条件:1.1 Reagents: Ammonia,Sodium Dithionite Solvents: Water; 75 Min,Rt; Ph 8,Rt; 3 H,75 °C
标题:Pyrazine-2,5-Diamines As Novel Oxidation Dye Precursors Of The Developer Type
参考文献:Germany]

= 932-52-5
反应条件:1.1 Reagents: Ammonia,Sodium Thiosulfate Solvents: Water; Ph 8,Rt; 3 H,75 °C; 75 °C -> 15 °C
标题:Preparation Of Pyrido[3,2-D]Pyrimidine As Pi3Kδ Inhibitors
参考文献:World Intellectual Property Organization]

= 932-52-5
反应条件:1.1 Solvents: Ethanol; 48 H,Ph 10.2,80 °C
标题:Reaction Of Dextran Polyaldehyde With Aminohydroxypyrimidines
作者:Tishchenko,E. V.; Iozep,A. A.; Ivin,B. A.
参考文献:Russian Journal Of Applied Chemistry (Translation Of Zhurnal Prikladnoi Khimii) 日期:2002 卷标:75(4) 页码:680-682]

= 932-52-5 [标题:Reaction Conditions
标题:An Efficient Approach For The Synthesis Of 1,2,3-Triazole Moiety To Generate Uracil Molecular Architectures Through Cu-Catalyzed Azide-Alkyne Cycloaddition
作者:Mohamed,Asmaa H.
参考文献:Journal Of Heterocyclic Chemistry 日期:2019 卷标:56(10) 页码:2831-2838]

= 932-52-5 [标题:Reaction Conditions
标题:Antimetabolites Of Nucleic Acid. I. Synthesis Of 5-Amino-6-Azauracil Derivatives And Their Biological Activities
作者:Asano,Shingo; Kitamura,Jiro; Takatori,Kichitaro
参考文献:Yakugaku Zasshi 日期:1972 卷标:92(6) 页码:781-4]

= 932-52-5 + 141-82-2 + 617-45-8 + 6915-15-7 + 80-69-3 + 66-22-8 + 2577-38-0 + 134434-28-9 + 1068-84-4 + 496-76-4 + 57-13-6 + 68-94-0 + 65-86-1 + 73-24-5 + 73-40-5 + 79-14-1
反应条件:1.1 Reagents: Ammonium Chloride Solvents: Water; 3 - 30 D,38 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 24 H,110 °C
标题:New Insights Into The Characterization Of 'Insoluble Black Hcn Polymers'
作者:Ruiz-Bermejo,Marta; De La Fuente,Jose L.; Rogero,Celia; Menor-Salvan,Cesar; Osuna-Esteban,Susana; Et Al
参考文献:Chemistry & Biodiversity 日期:2012 卷标:9(1) 页码:25-40

2(1H)-嘧啶酮,5,6-二氨基-置于genes From Klebsiella Pneumoniae Subsp. Pneumoniae体系中,用 Aq. Buffer 作为反应溶剂,化学反应生成 5-氨基尿嘧啶
参考文献:Discovery Of A Bacterial 5-Methylcytosine Deaminase
标题:Discovery Of A Bacterial 5-Methylcytosine Deaminase
摘要:5-Methylcytosine Is Found In All Domains Of Life,But The Bacterial Cytosine Deaminase From Escherichia Coli (Coda) Will Not Accept 5-Methylcytosine As A Substrate. Since Significant Amounts Of 5-Methylcytosine Are Produced In Both Prokaryotes And Eukaryotes,This Compound Must Eventually Be Catabolized And The Fragments Recycled By Enzymes That Have Yet To Be Identified. We Therefore Initiated A Comprehensive Phylogenetic Screen For Enzymes That May Be Capable Of Deaminating 5-Methylcytosine To Thymine. From A Systematic Analysis Of Sequence Homologues Of Coda From Thousands Of Bacterial Species,We Identified Putative Cytosine Deaminases Where A "Discriminating" Residue In The Active Site,Corresponding To Asp-314 In Coda From E. Coli,Was No Longer Conserved. Representative Examples From Klebsiella Pneumoniae (Locus Tag: Kpn00632),Rhodobacter Sphaeroides (Locus Tag: Rsp0341),And Corynebacterium Glutamicum (Locus Tag: Ncgl0075) Were Demonstrated To Efficiently Deaminate 5-Methylcytosine To Thymine With Values Of K(Cat)/k-M Of 1.4 X 10(5),2.9 X 10(4),And 1.1 X 10(3) M-1 S(-1),Respectively. These Three Enzymes Also Catalyze The Deamination Of 5-Fluorocytosine To 5-Fluorouracil With Values Of K(Cat)/k-M Of 1.2 X 10(5),6.8 X 10(4),And 2.0 X 10(2) M-1 S(-1),Respectively. The Three-Dimensional Structure Of Kpn00632 Was Determined By X-Ray Diffraction Methods With 5-Methylcytosine (Pdb Id: 4R85),5-Fluorocytosine (Pdb Id: 4R88),And Phosphonocytosine (Pdb Id: 4R7W) Bound In The Active Site. When Thymine Auxotrophs Of E. Coli Express These Enzymes,They Are Capable Of Growth In Media Lacking Thymine When Supplemented With 5-Methylcytosine. Expression Of These Enzymes In E. Coli Is Toxic In The Presence Of 5-Fluorocytosine,Due To The Efficient Transformation To 5-Fluorouracil.
DOI:10.1021/bi5012767

专利信息

专利号:US-2007049757-A1
优先权日:2005-08-26
标题:Methods for the synthesis of substituted amino uracils
发明人：RIEGER JAYSON M; THOMPSON ROBERT
权利人:RIEGER JAYSON M; THOMPSON ROBERT
摘要:The invention provides novel methods of preparing substituted amino uracil compounds that can be employed as useful intermediates in the synthesis of various xanthines. Highly regioselective unsymmetrical amino uracils can be obtained using these methods which is a particular advantage over other existing methods.

专利号:US-9221821-B2
优先权日:2012-06-05
标题:Methods for the synthesis of 1,3-substituted aminouracils and other xanthine-related compounds
发明人：DIEP NHUT; KALYAN YURIY B
权利人:FOREST LAB HOLDINGS LTD; FOREST LAB HOLDINGS LTD
摘要:Methods for the synthesis of disubstituted aminouracils and xanthine and/or xanthine-related compounds are provided.

专利号:US-5075446-A
优先权日:1989-12-29
标题:Synthesis of tetrahydro-2-furylated pyrimidine derivatives
发明人：KIM YONG H; LEE CHUN H
权利人:KOREA ADVANCED INST SCI & TECH
摘要:The synthesis of 1-(tetrahydro-2-furyl) pyrimidine derivatives in good yields by the reaction of trimethylsilylated pyrimidine bases with 2-acetoxytetrahydrofuran using a catalytic amount of cesium chloride in acetonitrile under mild conditions is described.

专利号:US-4849513-A
优先权日:1983-12-20
标题 :Deoxyribonucleoside phosphoramidites in which an aliphatic amino group is attached to the sugar ring and their use for the preparation of oligonucleotides containing aliphatic amino groups
发明人：SMITH LLOYD M; FUNG STEVEN; KAISER ROBERT J
权利人:CALIFORNIA INST OF TECHN
摘要:The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permitting amino groups to be selectively placed at any position on oligonucleotides of any composition or length which is attainable by current DNA synthetic methods. Fluorescent dyes or other detectable moieties may be covalently attached to the amino groups to yield the corresponding modified oligonucleotide.

专利号:US-5118802-A
优先权日:1983-12-20
标题:DNA-reporter conjugates linked via the 2' or 5'-primary amino group of the 5'-terminal nucleoside
发明人：SMITH LLOYD M; FUNG STEVEN; KAISER JR ROBERT J
权利人:CALIFORNIA INST OF TECHN
摘要:The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permitting amino groups to be selectively placed at any position on oligonucleotides of any composition or length which is attainable by current DNA synthetic methods. Fluorescent dyes or other detectable moieties may be covalently attached to the amino groups to yield the corresponding modified oligonucleotide.

专利号:US-5866700-A
优先权日:1993-12-17
标题:Solid-phase synthesis of oligoribonucleotides
发明人：PFLEIDERER WOLFGANG; SCHNELL RALF; MATYSIAK STEPHAN
权利人:HOECHST AG
摘要:A process for the preparation of oligoribonucleotides of the formula in which n, L, BB, W, T, Y', U, C1 and C2 are as defined in the description, by solid-phase synthesis is described, as are intermediates of the oligoribonucleotides.

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合成参考文献

摘要:G.B. Barlin and W. Pfleiderer. J. Chem. Soc., B 1971.
参考文献:10.1007/bf02976623
摘要:Fathalla OA, Zaghary WA, Radwan HH, Awad SM, Mohamed MS. Synthesis of new 2-thiouracil-5-sulfonamide derivatives with biological activity. Archives of Pharmacal Research. 2002 Jun;25(3):258–69. doi: 10.1007/bf02976623.

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CAS: 932-52-5; 5-Aminopyrimidine-2,4(1H,3H)-Dione

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MSDS等安全信息

欧盟法规

上下游产品

合成工艺路线路线简述

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