Green, Catalyst-Free Synthesis of Mesalazine Conjugates

Abstract

A greener protocol for the synthesis of mesalazine conjugates is reported. Mesalazine conjugates are prepared in high yields by a one-pot reaction of mesalazine and aminoacyl/peptidoylbenzotriazoles in water under microwave irradiation.

Key words

mesalazine - amino acid - prodrug - green chemistry - benzotriazole methodology

• References

• 1 Podolsky DK. New Engl. J. Med. 1991; 325: 928
• 2 Crotty B, Jewel DP. Br. J. Clin. Pharmacol. 1992; 34: 189
• 3 Novis BH, Korzets Z, Chen P, Bernheim J. Br. Med. J. 1988; 296: 1442
• 4 Scheline RR. Pharmacol. Rev. 1973; 25: 451
• 5 Boxenbaum HG, Jodhka GS, Ferguson AC, Riegelman S, MacGregor TR. J. Pharmacokinet. Biopharm. 1974; 2: 211
• 6 Nakamura J, Asai K, Nishida K, Sasaki H. Chem. Pharm. Bull. 1992; 40: 2164
• 7 Jung YJ, Lee JS, Kim HH, Kim YM, Han S. Arch. Pharm. Res. 1998; 21: 174
• 8 Jung YJ, Lee JS, Kim YM. J. Pharm. Sci. 2001; 90: 1767
• 9 Katritzky AR, Lan X, Yang JZ, Denisko OV. Chem. Rev. 1998; 98: 409
• 10 Lebedyeva IO, Povstyanoy MV, Ryabitskii AB, Povstyanoy VM. J. Heterocycl. Chem. 2010; 47: 368
• 11 Chakraborti AK, Rudrawar S, Jadhav KB, Kaur G, Chankeshwara SV. Green Chem. 2007; 9: 1335
• 12 Panda SS, Ibrahim MA, Küçükbay H, Meyers MJ, Sverdrup FM, El-Feky SA, Katritzky AR. Chem. Biol. Drug Des. 2013; 82: in press; DOI: 10.1111/cbdd.12134
• 13 Panda SS, Bajaj K, Meyers MJ, Sverdrup FM, Katritzky AR. Org. Biomol. Chem. 2012; 10: 8985
• 14 Katritzky AR, Angrish P, Todadze E. Synlett 2009; 2392
• 15 Bajaj K, Panda SS, El-Nachef C, Katritzky AR. Chem. Biol. Drug Des. 2012; 80: 17