Synthesis and biological evaluation of neutrophilic inflammation inhibitors

Babior, 1984, Oxidants from phagocytes: agents of defence and destruction, Blood, 64, 959, 10.1182/blood.V64.5.959.959 Hamers, 1985, Oxidative stress in human neutrophilic granulocites: host defence and self-defence, 351 Malech, 1987, Neutrophils in human diseases, New Engl. J. Med., 317, 687, 10.1056/NEJM198709103171107 Styrt, 1989, The role of phagocytes in non infectious disease, 145 Henson, 1987, Tissue injury in inflammation: oxidants, proteases and cationic proteins, J. Clin. Invest., 79, 669, 10.1172/JCI112869 Weiss, 1989, Tissue destruction by neutrophils, New Engl. J. Med., 320, 356 Nathan, 1989, Respiratory burst in adherent human neutrophils: triggering by colony-stimulating factor CSF-GM and CSF-G, Blood, 73, 301, 10.1182/blood.V73.1.301.301 Babior, 1973, Biological defence mechanism. The production by leukocytes of superoxide, a potential bactericidal agent, J. Clin. Invest., 52, 741, 10.1172/JCI107236 Sassone-Corsi, 1994, Goals for signal transduction pathways: linking up transcriptional regulation, EMBO J., 13, 4717, 10.1002/j.1460-2075.1994.tb06797.x Nishizuka, 1995, Protein kinase C and lipid signalling for sustained cellular responses, FASEB J., 69, 484, 10.1096/fasebj.9.7.7737456 Quilliam, 1991, Rapl A is a substrate for cyclic AMP-dependent protein kinase in human neutrophils, J. Immunol., 147, 1628, 10.4049/jimmunol.147.5.1628 Mueller, 1992, Reversal of inhibitory pathways in neutrophils by protein kinase antagonist: a rational approach to the restoration of depressed cell function?, J. Leukocyte Biol., 52, 400, 10.1002/jlb.52.4.400 Wright, 1990, Differential inhibition of human neutrophils function. Role of cyclic AMP-specific, cyclic GMP-insensitive phosphodiesterase, Biochem. Pharmacol., 40, 699, 10.1016/0006-2952(90)90304-4 Bevilacqua, 1994, Nimesulide decrease superoxide production by inhibiting phosphodiesterase tipe IV, Eur. J. Pharmacol., 268, 415, 10.1016/0922-4106(94)90067-1 Torphy, 1998, Phosphodiesterase isozymes. Molecular target for novel antiasthma agents, Am. J. Resp. Crit. Care Med., 157, 351, 10.1164/ajrccm.157.2.9708012 Crocker, 1999, Therapeutical potential of phosphodiesterase 4 inhibitors in allergic diseases, Drugs Today, 35, 519, 10.1358/dot.1999.35.7.548265 Doherty, 1999, Phosphodiesterase 4 inhibitors as novel anti-inflammatory agents, Curr. Op. Chem. Biol., 3, 466, 10.1016/S1367-5931(99)80068-4 Palfreyman, 1996, Phosphodiesterase type IV inhibitors, vol. 33, 1 Stafford, 1996, Chronic pulmonary inflammation and other therapeutic applications of PDE IV inhibitors, Annu. Rep. Med. Chem., 13, 71, 10.1016/S0065-7743(08)60447-9 Norman, 1998, PDE4 inhibitors 1998, Exp. Opin. Ther. Pat., 8, 771, 10.1517/13543776.8.7.771 Burnouf, 1998, Phosphodiesterase inhibitors, Annu. Rep. Med. Chem., 33, 91, 10.1016/S0065-7743(08)61075-1 Norman, 1999, PDE4 inhibitors 1999, Exp. Opin. Ther. Pat., 9, 1101, 10.1517/13543776.9.8.1101 Schmiechen, 1977 Duplantier, 1996, Biarylcarboxylic acids and -amides: inhibition of phosphodiesterase type IV versus [3H]rolipram binding activity and their relationship to emetic behavior in the ferret, J. Med. Chem., 39, 120, 10.1021/jm9505066 Barnette, 1995, J. Pharmacol. Exp. Ther., 273, 1396 Saccomano, 1991, Calcium-independent phosphodiesterase inhibitors as putative antidepressants: [3-(bicycloalkyloxy)-4-methoxyphenyl-2-imidazolidinones, J. Med. Chem., 34, 291, 10.1021/jm00105a045 Marivet, 1989, Inhibition of cyclic adenosine-3′,5′-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogues, J. Med. Chem., 32, 1450, 10.1021/jm00127a009 Polymeropoulos, 1997, A pharmacophore model for PDE IV inhibitors, Quant. Struct. Act. Relat., 16, 231, 10.1002/qsar.19970160307 Polymeropou, 1999, A peptidic binding site model for PDE4 inhibitors, Quant. Struct. Act. Relat., 18, 543, 10.1002/(SICI)1521-3838(199912)18:6<543::AID-QSAR543>3.0.CO;2-V Fossa, 2001, An update topographical model for phosphodiesterase 4 (PDE4) catalytic site, Quant. Struct. Act. Relat., 20, 17, 10.1002/1521-3838(200105)20:1<17::AID-QSAR17>3.0.CO;2-X Xu, 2000, Atomic structure of PDE4: insights into phosphodiesterase mechanism and specificity, Science, 288, 1822, 10.1126/science.288.5472.1822 Bruno, 1999, Antiinflammatory agents: new series of N-substituted amino acids with complex pyrimidine structures endowed with antiphlogistic activity, Il Farmaco, 54, 95, 10.1016/S0014-827X(98)00109-8 Bruno, 2000, Synthesis and pharmacological screening of novel non-acid gastroprotective antipyretic antiinflammatory agents with antiplatelet properties, Arzneimittel Forsch. Drug Res., 50, 140 Dallegri, 1999, Cefoperazone prevents the inactivation of α1-antitrypsin by activated neutrophils, Antimicrob. Agent. Chemiotherap., 43, 2307, 10.1128/AAC.43.9.2307 Souness, 1995, Suppression of eosinophils function by RP 73401, a potent and selective inhibitor of cyclic AMP-specific phosphodiesterase comparison with rolipram, Br. J. Pharmacol., 115, 39, 10.1111/j.1476-5381.1995.tb16317.x Barnette, 1998, SB207499 (Ariflo), a potent and selective second generation phosphodiesterase 4 inhibitor: in vitro anti-inflammatory actions, J. Pharmacol. Exp. Ther., 284, 420 Harbinson, 1977, The effect of a novel orally-active selective PDE4 isoenzyme inhibitor (CDP840) on allergen-induced responses in asthmatic subjects, Eur. Respir. J., 10, 1008, 10.1183/09031936.97.10051008 Ashton, 1994, Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues, J. Med. Chem., 37, 1696, 10.1021/jm00037a021 Sunggak, 1985, Zinc-modified cyanoborohydride as a selective reducing agent, J. Org. Chem., 50, 1927, 10.1021/jo00211a028 Borch, 1971, The cyanohydridoborate anion as a selective reducing agent, JACS, 93, 2897, 10.1021/ja00741a013 V.L. Cohan, E.F. Kleinman, Isoxazoline compounds as inhibitors of TNF release, Chem. Abstr. 124: 11, 7297 (1999) Dankberg, 1976, A test of granulocyte membrane integrity and phagocytic function, Cryobiology, 13, 430, 10.1016/0011-2240(76)90098-5 Dapino, 1993, Induction of neutrophils respiratory burst by tumor necrosis factor alpha; priming effect of solid phase fibronectin and intervention of CD11b–CD18 integrins, Clin. Exp. Immunol., 94, 533, 10.1111/j.1365-2249.1993.tb08230.x Leslie, 1987, Evaluation and improvement of rapid microassay for measuring superoxide anion production by phagocytes. Spectrophotometric aspect, J. Immunol. Methods, 103, 253, 10.1016/0022-1759(87)90297-3 Weishaar, 1986, Multiple molecular forms of cyclic nucleotide phosphodiesterase in cardiac and smooth muscle and in platelets, Biochem. Pharmacol., 35, 787, 10.1016/0006-2952(86)90247-9 Torphy, 1992, Stimulation of beta adrenoceptors in a human monocyte cell line (U937) up-regulates cyclic AMP-specific phosphodiesterase activity, J. Pharmacol. Exp. Ther., 263, 1195