Acute and chronic anti-inflammatory evaluation of imidazo[1,2-a]pyridine carboxylic acid derivatives and docking analysis

Acosta SL, Muro LV, Sacerio AL, Monteagudo GL, Peña AR, Okwei SN (2003) Anti-inflammatory effects of an aqueous extract of Capraria biflora L. Acta Farm Bonaerense 22(1):53–55

Arumugam P, Gayatri PN, Subathra M, Ramesh A (2008) Anti-inflammatory activity of four solvents fractions of ethanol extract of Mentha spicata L. investigated on acute and chronic inflammation induced rats. Environ Toxicol Pharm 26:92–95

Borea PA, Varani K, Gessi S, Gilli P, Dalpiaz A (1998) Receptor binding thermodynamics as a tool for linking drug efficacy and affinity. Farmaco 53(4):249–254

Brooijmans N, Kuntz ID (2003) Molecular recognition and docking algorithms. Ann Rev Biophys Biomol Struct 32:335–373

Clària J (2003) Cyclooxygenase-2 biology. Curr Pharm Design 9:2177–2190

ChemSilico. https://secure.chemsilico.com/index.php . Accessed 15 April 2011

Dharmasiri MG, Jayakody JRAC, Galhena G, Liyanage SSP, Ratnasooriya WD (2003) Antiinflammatory and analgesic activities of mature fresh leaves of Vitex negundo. J Ethnopharmacol 87:199–206

Filipponi E, Cecchetti V, Tabarrini O, Bonelli D, Fravolini A (2000) Chemometric rationalization of the structural and physicochemical basis for selective cyclooxygenase-2 inhibition: toward more specific ligands. J Comput Aided Mol Des 14:277–291

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Peterson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98, Revision A.9. Gaussian, Inc., Pittsburgh

Gómez-Zaleta B, González-De la Rosa CH, Pérez-Hernández G, Beltrán HI, Aparicio F, Rojas-Hernández A, Rojo-Domínguez A (2008) Molecular speciation effect on docking and drug design. A computational study for mangiferin, a carbohydrate-polyphenol bioconjugate as a test case. J Mex Chem Soc 52(1):78–87

González PR, Poza GP, Vives R, Canto G (2002) Antiinflamatorios inhibidores selectivos de la ciclooxigenasa-2 (COX-2). Alergol Inmunol Clin 17:247–254

Gupta M, Mazumdar UK, Sivakumar T, Vamsi MLM, Karki SS, Sambathkumar R, Manikandan L (2003) Evaluation of anti-inflammatory activity of chloroform extract of Bryonia laciniosa in experimental animal models. Biol Pharm Bull 26:1342–1344

Huang M-T, Ghal G, Ho C-T (2004) Inflammatory process and molecular targets for anti-inflammatory nutraceuticals. Compr Rev Food Sci Food Saf 3:127–139

Humphrey W, Dalke A, Schulten K (1996) VMD: visual molecular dynamics. J Mol Graph 14:33–38

Isis/draw. http://www.mdli.com/ . Accessed 5 February 2011

Kale M, Misar AV, Dave V, Joshi M, Mujumdar AM (2007) Anti-inflammatory activity of Dalbergia lanceolaria bark ethanol extract in mice and rats. J Etnopharmacol 112:300–304

Mannhold R, Poda GI, Ostermann C, Tetko IV (2009) Calculation of molecular lipophilicity: state of the art and comparison of Log P methods on more than 96000 compounds. J Pharm Sci 98(3):861–893

Márquez-Flores YK, Campos-Aldrete ME, Salgado-Zamora H, Correa-Basurto J, Meléndez-Camargo ME (2011) Docking simulations, synthesis, and anti-inflammatory activity evaluation of 2-(N-alkyl)amino-3-nitroimidazo[1,2-a]pyridines. Med Chem Res. doi: 10.1007/s00044-011-9585-5

Maruyama Y, Anami K, Terasawa M, Goto K, Imayoshi T, Kadobe Y, Mizushima Y (1981) Antiinflammatory activity of an imidazopyridine derivative (miroprofen). Arzneim Forsch 31(7):1111–1118

Marzocco S, Di Paola R, Serraino I, Sorrentino R, Meli R, Mattaceraso G, Cuzzocrea S, Pinto A, Autire G (2004) Effect of methylguanidine in carrageenan-induced acute inflammation in the rats. Eur J Pharm 484:341–350

Mehanna AS (2003) NSAIDs: chemistry and pharmacological actions. Am J Pharm Educ 67(2):1–7

Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ (1998) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19:1639

Noguez MNA, Rubio MA, Rojas OI, Chávez CAE (2009) Determinación del coeficiente de partición y del pKa de la 4, 4′- diaminodifenilsulfona a partir de datos de solubilidad. Revista Mexicana de Ciencias Farmacéuticas 40(1):12–18

Pedernera AM, Guardia T, Guardia CC, Ester RA, de la Rocha NE, Di Genaro S, Pelzer LE (2006) Anti-ulcerogenic and anti-inflammatory activity of the methanolic extract of Larrea divaricata Cav. in rat. J Ethnopharmacol 105:415–420

Perianayagam JB, Sharma SK, Pillai KK (2006) Anti-inflammatory activity of Trichodesma indicum root extract in experimental animals. J Ethnopharmacol 104:410–414

Praveen RPN, Knaus EE (2008) Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond. J Pharm Pharm Sci 11(2):81s–110s

Rathi A, Rao ChV, Ravishankar B, De S, Mehrotra S (2004) Anti-inflammatory and anti-nociceptive activity of the water decoction Desmodium gangeticum. J Ethnopharmacol 95:259–263

Secretaría de Agricultura, Ganadería, Desarrollo Rural, Pesca y Alimentación (1999) Technical specifications for the production, care and use of laboratory animals. Official Mexican Standard. NOM-062.ZOO

VCCLAB. Virtual Computation Chemistry Laboratory. http://146.107.217.178/lab/alogps/start.html . Accessed 20 March 2011

Viji V, Helen A (2008) Inhibition of lipoxygenases and cyclooxygenase-2 enzymes by extracts isolated from Bacopa monniera (L.) Wettst. J Ethnopharmacol 118:305–311

Warshakoon NC, Wu S, Boyer A, Kawamoto R, Sheville J, Renock S, Xu K, Pokross M, Evdokimov AG, Walter R, Mekel M (2006) A novel series of imidazo[1, 2-a]pyridine derivatives as HIF-1a prolyl hydroxylase inhibitors. Bioorg Med Chem Lett 16:5598–5601

Winkelmann E, Raether W, Hartung H, Wagner WH (1977) Chemotherapeutisch wirksame nitroverbindungen. 3. Mitteilung: nitropyridine, nitroimidazopyridine und vezwandte verbindugen. Arzneim Forsch 27:82–89