Simple and rapid synthesis of some nucleoside derivatives: structural and spectral characterization

Abstract: In our present investigation a new series of nucleoside derivatives (2-13) were synthesized from uridine (1) via only two step reactions by direct acylation method. Firstly, uridine (1) was treated with 4-t-butylbenzoyl chloride in pyridine at -5?C and afforded the 5´-O-(4-t-butylbenzoyl)uridine derivative (2) in an excellent yield. In order to obtain newer products, the 5´-O-uridine derivative was further transformed to a series of 2´,3´-di-O-acyl derivatives (2-13) containing a wide variety of functionalities in a single molecular framework. The yields of the compounds were more than 80%. The synthesized titled compounds were characterized by their physical properties, FTIR (Fourier transform infrared spectroscopy), 1H-NMR (Nuclear magnetic resonance) spectroscopy and elemental analysis.

How to cite this paper

 Chowdhury, S., Bhuiyan, M., Ozeki, Y & Kawsar, S. (2016). Simple and rapid synthesis of some nucleoside derivatives: structural and spectral characterization.Current Chemistry Letters, 5(2), 83-92.

Refrences

1 Clercq D. E. (2011) The clinical potential of the acyclic (and cyclic) nucleoside phosphonates. The magic of the phosphonate bond. Biochem. Pharmacol., 82 (2) 99-109.

2 Miura S., and Izuta S. (2004) DNA polymerases as targets of anticancer nucleosides. Curr. Drug Targets, 5 (2) 191-195.

3 Bonate P. L., Arthaud L., Cantrell W. R., Stephenson K., Secrist J. A., and Weitman S. (2006) Discovery and development of clofarabine: A nucleoside analogue for treating cancer. Nat. Rev. Drug Discovery, 5 (10) 855-863.

4 Yamamoto T., Koyama H., Kurajoh M., Shoji T., Tsutsumi Z., and Moriwaki Y. (2011) Biochemistry of uridine in plasma. Clin. Chimica Acta, 412 (19) 1712-1724.

5 Rachakonda S., and Cartee L. (2004) Challenges in antimicrobial drug discovery and the potential of nucleoside antibiotics. Curr. Med. Chem., 11 (6) 775-793.

6 Dobolyi A., Juh?sz G., Kov?cs Z., and Kardos J. (2011) Uridine function in the central nervous system. Curr. Topics Med. Chem., 11 (8) 1058-1067.

7 Cansev M. (2006) Uridine and cytidine in the brain: Their transport and utilization. Brain Res. Rev., 52 (2) 389-397.

8 Geiger A., and Yamasaki S. (1956) Cytidine and uridine requirement of the brain. J. Neurochem., 1 (2) 93-100.

9 Hayakawa H., Ashizawa H., Tanaka H., and Miyasaka T. (1990) Introduction of an alkyl group into the sugar portion of uracilnucleosides by the use of gilman reagents. Chem. Pharm. Bull., 38 (2) 355-360.

10 Williams J., and Richardson A. (1967) Selective acylation of pyranoside—i.: Benzoylation of methyl ?-D-glycopyranosides of mannose, glucose and galactose. Tetrahedron, 23 (3) 1369-1378.

11 Kim S., Chang H., and Kim W. J. (1985) Selective benzoylation of diols with 1-(benzoyloxy) benzotriazole. J. Org. Chem., 50 (10) 1751-1752.

12 Wagner D., Verheyden J. P., and Moffatt J. G. (1974) Preparation and synthetic utility of some organotin derivatives of nucleosides. J. Org. Chem., 39 (1) 24-30.

13 Kawsar S. M., Mymona K., Asma R., Manchur M. A., Koide Y., and Ozeki Y. (2015) Infrared,1H-NMR spectral studies of some methyl 6-O-myristoyl-?-D-glucopyranoside derivatives: Assessment of antimicrobial effects. Int. Lett. Chem. Phys. Astron., 58, 122-136.

14 Gupta R., Paul S., Gupta A., Kachroo P., and Bani S. (1997) Synthesis and biological activities of some 2-substituted phenyl-3-(3-alkyl/aryl-5, 6-dihydro-s-triazolo-3,4-b1,3,4thiadiazol-6-yl) indoles. Ind. J. Chem., Sect. B:, 36 (8) 707-710.

15 Singh H., Shukla K. N., Dwivedi R., and Yadav L. D. S. (1990) Cycloaddition of 4-amino-3-mercapto-1, 2, 4-triazole to heterocumulenes and antifungal activity of the resulting 1, 2, 4-triazolo [3, 4-c]-1, 2-dithia-4, 5-diazines. J. Agric. Food Chem., 38 (7) 1483-1486.

16 Kabir A., Dutta P., and Kawsar S. M. (2004) Biological evaluation of some derivatives of methyl-?-D-mannopyranoside. Bull. Pure Appl. Sci., 23 (1) 39-45.

17 Kabir A., Kawsar S. M., Bhuiyan M., Islam M., and Rahman M. (2004) Biological evaluation of some mannopyranoside derivatives. Bull. Pure Appl. Sci., 23 (2) 83-91.

18 Kabir A., Matin M., and Kawsar S. M. (1998) Synthesis and antibacterial activities of some uridine derivatives. Chittagong Univ. J. Sci., 22 (1) 13-18.

19 Kawsar S. M., Ferdous J., Mostafa G., and Manchur M. (2014) A synthetic approach of D-glucose derivatives: Spectral characterization and antimicrobial studies. Chem. Chem. Technol., 8 (1) 19-27.

20 Kabir A., Kawsar S. M., Bhuiyan M., Rahman M. S., and Banu B. (2008) Biological evaluation of some octanoyl derivatives of methyl 4,6-O-cyclohexylidene-?-D-glucopyranoside. Chittagong Univ. J. Biol. Sci., 3 (1 & 2) 53-64.

21 Kawsar S. M., Faruk M. O., Rahman M. S., Fujii Y., and Ozeki Y. (2014) Regioselective synthesis, characterization, and antimicrobial activities of some new monosaccharide derivatives. Sci. Pharm., 82 (1) 1-20.

22 Kawsar S. M., Islam M. M., Chowdhury S. A., Hasan T., Hossain M. K., Manchur M. A., and Ozeki Y. (2013) Design and newly synthesis of some 1,2-O-isopropylidene-?-D-glucofuranose derivatives: Characterization and antibacterial screening studies. Hacett. J. Biol. Chem., 41 (3) 195-206.

23 Kawsar S. M., Uddin S., Nishat S. S. B. S., Manchur M. A., and Ozeki Y. (2015) Synthesis, characterization and antibacterial susceptibility of some benzenesulfonyl and N-acetylsulfanilyl derivatives of methyl ?-D-glucopyranoside. Curr. Res. Chem., 7 (2) 21-33.

24 Kawsar S. M., Uddin S., Manchur M. A., Fujii Y., and Ozeki Y. (2015) Acylation of D-glucose derivatives over C5H5N: Spectral characterization and in vitro antibacterial activities. Int. J. Biol. Chem., 9 (6) 269-282.