合成路线:Idoxuridine can be obtained by several related ways:1) The reaction of 5-iodouracil (I) with refluxing POCl3 and dimethylaniline gives 2,4-dichloro-5-iodopyrimidine (II),which by reaction with NaOCH3 in refluxing methanol,is converted into 2,4-dimethoxy-5-iodopyrimidine (III).The reaction of (III) with 2-deoxy-3,6-di-O-p-toluoyl-D-ribofuranosyl chloride (IV) in acetonitrile yields the ribofuranosyl pyridone (V),which is demethylated with acetic anhydride - dry HCl to afford 2'-deoxy-5-iodo-3',6'-di-O-p-toluoyluridine (VI).Finally,this compound is hydrolyzed with NaOCH3 in methanol.2) The acetylation of 5-iodouracil (I) with refluxing acetic anhydride gives 1-acetyl-5-iodouracil (VII),which by reaction with mercuric acetate in refluxing methanol is converted into the corresponding mercurium salt (VIII).The condensation of (VIII) with the ribofuranosyl chloride (IV) in chloroform affords the protected 2'-deoxy-5-iodouridine (VI),already obtained.3) The iodination of 2'-deoxyuridine (IX) with iodine,iodic acid,acetic anhydride,CCl4 and water gives 2'-deoxy-5,6-diiodo-5,6-dihydrouridine (X),which is then treated with NaOH to eliminate HI.4) By direct iodination of 2'-deoxyuridine (IX) with iodine and nitric acid in refluxing chloroform.
参考文献标题:A rapid method for the synthesis of 5-iodo-2'-deoxyuridine (IDR) and optimisation of the parameters
文献作者:Trivedi,M.A.
参考来源:J Label Compd Radiopharm 1993,33(7),607-12
合成路线:Idoxuridine can be obtained by several related ways:1) The reaction of 5-iodouracil (I) with refluxing POCl3 and dimethylaniline gives 2,4-dichloro-5-iodopyrimidine (II),which by reaction with NaOCH3 in refluxing methanol,is converted into 2,4-dimethoxy-5-iodopyrimidine (III).The reaction of (III) with 2-deoxy-3,6-di-O-p-toluoyl-D-ribofuranosyl chloride (IV) in acetonitrile yields the ribofuranosyl pyridone (V),which is demethylated with acetic anhydride - dry HCl to afford 2'-deoxy-5-iodo-3',6'-di-O-p-toluoyluridine (VI).Finally,this compound is hydrolyzed with NaOCH3 in methanol.2) The acetylation of 5-iodouracil (I) with refluxing acetic anhydride gives 1-acetyl-5-iodouracil (VII),which by reaction with mercuric acetate in refluxing methanol is converted into the corresponding mercurium salt (VIII).The condensation of (VIII) with the ribofuranosyl chloride (IV) in chloroform affords the protected 2'-deoxy-5-iodouridine (VI),already obtained.3) The iodination of 2'-deoxyuridine (IX) with iodine,iodic acid,acetic anhydride,CCl4 and water gives 2'-deoxy-5,6-diiodo-5,6-dihydrouridine (X),which is then treated with NaOH to eliminate HI.4) By direct iodination of 2'-deoxyuridine (IX) with iodine and nitric acid in refluxing chloroform.
参考文献标题:Idoxuridine
文献作者:Castar,J.; Robinson,C.
参考来源:Drugs Fut 1995,20(7),670
合成路线:Idoxuridine can be obtained by several related ways:1) The reaction of 5-iodouracil (I) with refluxing POCl3 and dimethylaniline gives 2,4-dichloro-5-iodopyrimidine (II),which by reaction with NaOCH3 in refluxing methanol,is converted into 2,4-dimethoxy-5-iodopyrimidine (III).The reaction of (III) with 2-deoxy-3,6-di-O-p-toluoyl-D-ribofuranosyl chloride (IV) in acetonitrile yields the ribofuranosyl pyridone (V),which is demethylated with acetic anhydride - dry HCl to afford 2'-deoxy-5-iodo-3',6'-di-O-p-toluoyluridine (VI).Finally,this compound is hydrolyzed with NaOCH3 in methanol.2) The acetylation of 5-iodouracil (I) with refluxing acetic anhydride gives 1-acetyl-5-iodouracil (VII),which by reaction with mercuric acetate in refluxing methanol is converted into the corresponding mercurium salt (VIII).The condensation of (VIII) with the ribofuranosyl chloride (IV) in chloroform affords the protected 2'-deoxy-5-iodouridine (VI),already obtained.3) The iodination of 2'-deoxyuridine (IX) with iodine,iodic acid,acetic anhydride,CCl4 and water gives 2'-deoxy-5,6-diiodo-5,6-dihydrouridine (X),which is then treated with NaOH to eliminate HI.4) By direct iodination of 2'-deoxyuridine (IX) with iodine and nitric acid in refluxing chloroform.
参考文献标题:Introduction of the 5-halogenated uracil moiety into deoxyribonucleic acid of mammalian cells in culture
文献作者:Cheong,L.; Rich,M.A.; Eidinoff,M.L.
参考来源:J Biol Chem 1960,235(5),1441-7
合成路线:Idoxuridine can be obtained by several related ways:1) The reaction of 5-iodouracil (I) with refluxing POCl3 and dimethylaniline gives 2,4-dichloro-5-iodopyrimidine (II),which by reaction with NaOCH3 in refluxing methanol,is converted into 2,4-dimethoxy-5-iodopyrimidine (III).The reaction of (III) with 2-deoxy-3,6-di-O-p-toluoyl-D-ribofuranosyl chloride (IV) in acetonitrile yields the ribofuranosyl pyridone (V),which is demethylated with acetic anhydride - dry HCl to afford 2'-deoxy-5-iodo-3',6'-di-O-p-toluoyluridine (VI).Finally,this compound is hydrolyzed with NaOCH3 in methanol.2) The acetylation of 5-iodouracil (I) with refluxing acetic anhydride gives 1-acetyl-5-iodouracil (VII),which by reaction with mercuric acetate in refluxing methanol is converted into the corresponding mercurium salt (VIII).The condensation of (VIII) with the ribofuranosyl chloride (IV) in chloroform affords the protected 2'-deoxy-5-iodouridine (VI),already obtained.3) The iodination of 2'-deoxyuridine (IX) with iodine,iodic acid,acetic anhydride,CCl4 and water gives 2'-deoxy-5,6-diiodo-5,6-dihydrouridine (X),which is then treated with NaOH to eliminate HI.4) By direct iodination of 2'-deoxyuridine (IX) with iodine and nitric acid in refluxing chloroform.
参考文献标题:Synthesis and biological activities of iododeoxyuridine,an analog of thymidine
文献作者:Prusoff,W.H.
参考来源:Biochim Biophys Acta 1959,32295-6
合成路线:Idoxuridine can be obtained by several related ways:1) The reaction of 5-iodouracil (I) with refluxing POCl3 and dimethylaniline gives 2,4-dichloro-5-iodopyrimidine (II),which by reaction with NaOCH3 in refluxing methanol,is converted into 2,4-dimethoxy-5-iodopyrimidine (III).The reaction of (III) with 2-deoxy-3,6-di-O-p-toluoyl-D-ribofuranosyl chloride (IV) in acetonitrile yields the ribofuranosyl pyridone (V),which is demethylated with acetic anhydride - dry HCl to afford 2'-deoxy-5-iodo-3',6'-di-O-p-toluoyluridine (VI).Finally,this compound is hydrolyzed with NaOCH3 in methanol.2) The acetylation of 5-iodouracil (I) with refluxing acetic anhydride gives 1-acetyl-5-iodouracil (VII),which by reaction with mercuric acetate in refluxing methanol is converted into the corresponding mercurium salt (VIII).The condensation of (VIII) with the ribofuranosyl chloride (IV) in chloroform affords the protected 2'-deoxy-5-iodouridine (VI),already obtained.3) The iodination of 2'-deoxyuridine (IX) with iodine,iodic acid,acetic anhydride,CCl4 and water gives 2'-deoxy-5,6-diiodo-5,6-dihydrouridine (X),which is then treated with NaOH to eliminate HI.4) By direct iodination of 2'-deoxyuridine (IX) with iodine and nitric acid in refluxing chloroform.
参考文献标题:Iodination of 2'-deoxycytidine and related substances
文献作者:Chang,P.K.; Welch,A.D.
参考来源:J Med Chem 1963,6428-30
合成路线:Idoxuridine can be obtained by several related ways:1) The reaction of 5-iodouracil (I) with refluxing POCl3 and dimethylaniline gives 2,4-dichloro-5-iodopyrimidine (II),which by reaction with NaOCH3 in refluxing methanol,is converted into 2,4-dimethoxy-5-iodopyrimidine (III).The reaction of (III) with 2-deoxy-3,6-di-O-p-toluoyl-D-ribofuranosyl chloride (IV) in acetonitrile yields the ribofuranosyl pyridone (V),which is demethylated with acetic anhydride - dry HCl to afford 2'-deoxy-5-iodo-3',6'-di-O-p-toluoyluridine (VI).Finally,this compound is hydrolyzed with NaOCH3 in methanol.2) The acetylation of 5-iodouracil (I) with refluxing acetic anhydride gives 1-acetyl-5-iodouracil (VII),which by reaction with mercuric acetate in refluxing methanol is converted into the corresponding mercurium salt (VIII).The condensation of (VIII) with the ribofuranosyl chloride (IV) in chloroform affords the protected 2'-deoxy-5-iodouridine (VI),already obtained.3) The iodination of 2'-deoxyuridine (IX) with iodine,iodic acid,acetic anhydride,CCl4 and water gives 2'-deoxy-5,6-diiodo-5,6-dihydrouridine (X),which is then treated with NaOH to eliminate HI.4) By direct iodination of 2'-deoxyuridine (IX) with iodine and nitric acid in refluxing chloroform.
参考文献标题:Nucleic acid components and their analogues.XLIII.Synthesis of anomeric 5-iodo-2'-deoxyuridines
文献作者:Prystas,M.; Sorm,F.
参考来源:Coll Czech Chem Commun 1964,29121-9
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