Abstract
With the emergence of high throughput screening of bioactive molecules, there is constant need for the development of new strategies for diversity-oriented synthesis. We describe here a novel one-pot multicomponent reaction for the synthesis of uracil derivatives using easily available starting materials. This new synthetic strategy provides easy access to diverse uracil derivatives in moderate to good yields.
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References
Loksha YM, Pedersen EB, Loddo R, La Colla Paolo (2009) Synthesis and anti-HIV-1 activity of 1-substiuted 6-(3-cyanobenzoyl) and [(3-cyanophenyl)fluoromethyl]-5-ethyluracils. Archiv der Pharmazie 342: 501–506. doi:10.1002/ardp.200900058
Safonova TS, Nemeryuk MP, Likhovidova MM, Grineva NA, Keremov AF, Solov’eva NP, Anisimova OS (2008) Synthesis, properties, and reactions of derivatives of 1,3-dimethyl-6-(5’-aminopyrimidylthio-6’)uracils. Pharm Chem J 42: 11–14. doi:10.1007/s11094-008-0046-5
Maruyama T, Kozai S, Demizu Y, Witvrouw M, Pannecouque C, Balzarini J, Snoecks R, Andrei G, De Clercq E (2006) Synthesis and anti-HIV-1 and anti-HCMV activity of 1-substituted 3-(3,5-dimethylbenzyl)uracil derivatives. Chem Pharm Bull 54: 325–333. doi:10.1248/cpb.54.325
Prachayasittikul S, Sornsongkhram N, Pingaew R, Worachartcheewan A, Ruchirawat S, Prachayasittikul V (2009) Synthesis of N-substituted 5-iodouracils as antimicrobial and anticancer agents. Molecules 14: 2768–2779. doi:10.3390/molecules14082768
Núñez CM, Pavani GM, Díaz-Gavilán M, Rodríguez-Serrano F, Gómez-Vidal AJ, Marchal AJ, Aránega A, Gallo AM, Espinosa A, Campos MJ (2006) Synthesis and anticancer activity studies of novel 1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)uracil and (6’-substituted)-7- or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H- or 9H-purines. Tetrahedron 62: 11724–11733. doi:10.1016/j.tet.2006.09.039
Semenov VE, Voloshina AD, Toroptzova EM, Kulik NV, Zobov VV, Giniyatullin RK, Mikhailov AS, Nikolaev AE, Akamsin VD, Reznik VS (2006) Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers. Eur J Med Chem 41: 1093–1101. doi:10.1016/j.ejmech.2006.03.030
Zhi C, Long Z, Gambino J, Xu W, Brown CN, Barnes M, Butler M, LaMarr W, Wright EG (2003) Synthesis of substituted 6-anilinouracils and their inhibition of DNA polymerase IIIC and gram-positive bacterial growth. J Med Chem 46: 2731–2739. doi:10.1021/jm020591z
Yagi K, Akimoto K, Mimori N, Miyake T, Kudo M, Arai K, Ishii S (2000) Synthesis and insecticidal/acaricidal activity of novel 3-(2,4,6-trisubstituted phenyl)uracil derivatives. Pest Manag Sci 56: 65–73. doi:10.1002/(SICI)1526-4998(200001)56:1<65::AID-PS90>3.0.CO;2-S
Herdewijn P (2000) Heterocyclic modifications of oligonucleotides and antisense technology. Antisense Nucleic Acid Drug Dev 10: 297–310. doi:10.1089/108729000421475
Kurreck J (2003) Antisense technologies: improvement through novel chemical modifications. Eur J Biochem 270: 1628–1644. doi:10.1046/j.1432-1033.2003.03555.x
Iyer RP, Roland A, Zhou W, Ghosh K (1999) Modified oligonucleotides—syntheses, properties, and applications. Curr Opin Mol Ther 1: 344–358
Chiu Yl, Rana Tm (2003) siRNA function in RNAi: a chemical modification analysis. RNA 9: 1034–1048. doi:10.1261/rna.5103703
Fustero S, Piera J, Sanz-Cervera FJ, Catalán S, Ramírezde Arellano C (2004) A versatile synthesis of fluorinated uracils in solution and on solid-phase. Org Lett 6: 1417–1420. doi:10.1021/ol049668z
Nieto MR, Coelho A, Martínez A, Stefanachi A, Sotelo E, Raviña E (2003) Synthesis of 1-substituted-6-methyluracils. Chem Pharm Bull 51: 1025–1028. doi:10.1248/cpb.51.1025
Gabel N, Binkley S (1958) Synthesis of 1-aryluracils. J Org Chem 23: 643–645. doi:10.1021/jo01098a629
Senda S, Hirota K, Notani J (1972) Pyrimidine and related compounds. XVI. Synthesis of 1,3-disubstituted 5-cyanouracil derivatives and related compounds. Chem Pharm Bull 20: 1380–1388
Snyder RH, Jones ER (1946) Synthesis of 4-hydroxyquinolines. III. A direct synthesis of β-substituted acrylic esters. J Am Chem Soc 68: 1253–1255. doi:10.1021/ja01211a034
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Pedgaonkar, Y.Y., Degani, M.S. & Iyer, R.P. Diversity-oriented, one-pot, multi-component synthesis of substituted uracil derivatives. Mol Divers 15, 263–267 (2011). https://doi.org/10.1007/s11030-010-9266-1
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DOI: https://doi.org/10.1007/s11030-010-9266-1