Abstract
A series of quinoline-3-carboxylic acid derivatives has been synthesized with easy reaction conditions (in aqueous micellar microreactors and using microwave irradiation) and tested for its biological activity against human African trypanosomiasis (HAT). From this series, several derivatives of quinoline-3-carboxylic acid such as 23 and 24 exhibited potent activity against Trypanosoma brucei in vitro and had low cytotoxicity. The combination of electron withdrawing and donating groups in the structure seems to be the crucial factor to inhibit T. brucei.
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Simarro PP, Jannin J, Cattand P (2008) Eliminating human African trypanosomiasis: where do we stand and what comes next. PLoS Med 5: 174. doi:10.1371/journal.pmed.0050055
Deborggraeve S, Koffi M, Jamonneau V, Bonsu FA, Queyson R, Simarro PP, Herdewijn P, Buscher P (2008) Molecular analysis of archived blood slides reveals an atypical human trypanosoma infection. Diagn Micro Infec Dis 61: 428–433. doi:10.1186/1475-2875-10-195
Joshi PP, Shegokar VR, Power RM, Herder S, Katti R, Salkar HR, Dani VS, Bhargava A., Jannin J, Truc P (2005) Human trypanosomiasis caused by Trypanosoma evansi in India: the first case report. Am J Trop Med Hyg 73: 491–495
Kumar N, Orenstein R, Uslan DZ, Berbari EF, Klein CJ, Windebank AJ (2006) Melarsoprol-associated multifocal inflammatory CNS illness in African trypanosomiasis. Neurology 66: 1120–1121. doi:10.1212/01.wnl.0000202519.59577
Organ World Health (1986) Tech Rep Ser 739: 1
Hradil P, Hlavac J, Soural M, Hajduch M, Kolar M, Vecerova R (2009) 3-Hydroxy-2-phenyl-4(1H)-quinolinones as promising biologically active compounds. Mini Rev Med Chem 9: 696–702
Darque A, Dumètre A, Hutter S, Casano G, Robin M, Pannecouque C, Azas N (2009) Synthesis and biological evaluation of new heterocyclic quinolinones as anti-parasite and anti-HIV drug candidates. Bioorg Med Chem Lett 19: 5962–5964. doi:10.1002/chin.201008164
Geyer JA, Prigge ST, Waters NC (2005) Targeting malaria with specific CDK inhibitors. BBA-Proteins Proteom 1745: 160–170. doi:10.1016/j.bbapap.2005.07.031
Samant BS, Saraf YP, Bhagwat SS (2006) Chlorination of aromatic compounds in micellar media: regioselectivity. J Colloid Interface Sci 302: 207–211. doi:10.1016/j.jcis.2006.06.007
Samant BS, Bhagwat SS (2011) A novel improvement in ArLPdF catalytic fluorination of aromatic compounds. Appl Cata A: Gen 394: 191–194. doi:10.1016/j.apcata.2010.12.039
Samant BS, Kabalka GW (2011) A novel catalytic process for trifluoromethylation of bromoaromatic compounds. Chem Comm 47: 7236–7238. doi:10.1039/C1CC12098K
Samant BS, Kabalka GW (2012) Hydrogenolysis-hydrogenation of aryl ethers: selectivity pattern. Chem Commun 48: 8658–8660. doi:10.1039/c2cc34454h
Samant BS (2008) Synthesis of 3-hydroxypyrid-2-ones from furfural for treatment against iron overload and iron deficiency. Eur J Med Chem 43: 1978–1982. doi:10.1016/j.ejmech.2007.11.013
Samant BS, Sukhthankar MG (2009) Synthesis and comparison of antimalarial activity of febrifugine derivatives including halofuginone. Med Chem 5: 293–300. doi:10.1016/j.ejmech.2007.11.013
Samant BS, Sukhthankar MG (2011) Compounds containing 2-substituted imidazole ring for treatment against human African trypanosomiasis. Bioorg Med Chem Lett 21: 1015–1018. doi:10.1016/j.bmcl.2010.12.040
Varma RS (1999) Expeditious solvent-free organic syntheses using microwave irradiation. Clean Technol Envioron 1: 132–147. doi:10.1007/s100980050018
Drugs for Neglected Diseases Initiative (DNDi) newsletter: Geneva, November 2008. http://www.dndi.org/newsletters/n17/en/10_1.html
Raether W, Seidenath H (1983) The activity of fexinidazole (HOE 239) against experimental infections with Trypanosoma cruzi, trichomonads and Entamoeba histolytica. Ann Trop Med Parasitol 77: 13–26
Jennings FW, Urquhart GM (1983) The use of the 2-substituted 5-nitroimidazole, fexinidazole (Hoe 239) in the treatment of chronic T. brucei infections in mice. Z Parasitenkd 69: 577–581
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Samant, B.S., Nyangari, N. A novel microwave synthesis of quinoline-3-carboxylic acid derivatives for treatment against human African trypanosomiasis. Mol Divers 16, 685–695 (2012). https://doi.org/10.1007/s11030-012-9401-2
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DOI: https://doi.org/10.1007/s11030-012-9401-2