Synthesis and biological studies of catechol ether type derivatives as potential phosphodiesterase (PDE) IV inhibitors

Archives of Pharmacal Research

Volumn 22, Issue 2, 1999, Pages 202-207

  Rhee, Chung K ^a   Kim, Jong Hoon ^a   Suh, Byung Chul ^a   Xiang, Myung Xik ^a   Youn, Yong Sik ^a   Bang, Won Young ^a   Kim, Euikyung ^a   Shin, Jae Kyu ^a   Lee, Younha ^a  

^a CJ Corporation   (South Korea)

Author keywords

Anti asthma therapy; Catechol ether type PDE IV inhibitors; Phosphodiesterase (PDE); Structure activity relationship (SAR)

Indexed keywords

3',5' CYCLIC NUCLEOTIDE PHOSPHODIESTERASE; PHOSPHODIESTERASE INHIBITOR; PHOSPHODIESTERASE IV;

ANIMAL; ARTICLE; DRUG ANTAGONISM; GUINEA PIG; MALE; RAT; SPRAGUE DAWLEY RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

3',5'-CYCLIC-NUCLEOTIDE PHOSPHODIESTERASE; ANIMALS; GUINEA PIGS; MALE; PHOSPHODIESTERASE INHIBITORS; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033110768     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02976547     Document Type: Article

References (17)

1. Ashton, M. J., Cook, D. C., Fenton, G., Karlsson, J. A., Palfreyman, M. N., Raeburn, D., Ratcliffe, A. J., Souness, J. E., Thurairatnam, S. and Vicker, N., Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. J. Med. Chem., 37, 1696-1703 (1994).
2. Barnette, M. S., Grous, M., Cieslinski, L. B., Burman, M., Christensen, S. B. and Torphy, T. J., Inhibitors of phosphodiesterase IV (PDE IV) increase acid secretion in rabbit isolated gastric glands: correlation between function and interaction with a high-affinity rolipram binding site. J. Pharmacol. Exp. Ther., 273, 1396-1402 (1995).
3. Beavo, J. A., Conti, M. and Heaslip, R. J., Multiple cyclic nucleotide phosphodiesterases. Mol. Pharmacol., 46, 399-405 (1994).
4. Beavo, J. A. and Reifsnyder, D. H., Primary sequence of cyclic nucleotide phosphodiesterase isozymes and the design of selective inhibitors. Trends Pharmacol. Sci., 11, 150-155 (1990).
5. Christensen, S. B., Guider, A., Forster, C. J., Gleason, J. G., Bender, P. E., Karpinski, J. M., DeWolf, W. E. Jr., Barnette, M. S., Underwood, D. C., Griswold, D. E., Cieslinski, L. B., Burman, M., Bochnowicz, S., Osborn, R. R., Manning, C. D., Grous, M., Hillegas, L. M., Bartus, J. O., Ryan, M. D., Eggleston, D. S., Haltiwanger, R. C. and Torphy, T. J., 1,4-Cyclohexanecarboxylates: potent and selective inhibitors of phosphodiesterase 4 for the treatment of asthma. J. Med. Chem., 41, 821-835 (1998).
6. IV) inhibitor, CP-80,633. J. Allergy Clin. Immunol., 95, 350 (1995) [Abstract].
7. Cortijo, J., Bou, J., Beleta, J., cardelus, I., Llenas, J., Motciool, E. and Gristwood, R. W., Investigation into the role of phosphodiesterase IV in broncho-relaxation, including studies with human bronchus. Br. J. Pharmacol., 108, 562-56 (1993).
8. Erneux, C., Van Sande, J., Milot, F., Cochaux, P., Decosster, C. and Dumont, J. E., A mechanism in the control of intracellular cAMP level: the activation of a calmodulin-sensitive phosphodiesterase by a rise of intracellular free calcium. Mol. Cell. Endocrinol., 43, 123-134 (1985).
9. Holbrook, M., Gozzard, N., James, T., Higgs, G. and Hughes, B., Inhibition of bronchospasm and ozone-induced airway hyperresponsiveness in the guinea-pig by CDP840, a novel phosphodiesterase type 4 inhibitor. Br. J. Pharmacol., 118, 1192-1200 (1996).
10. Kammer, G. M. The adenylate cyclase-cAMP-protein kinase pathway and regulation of immune response. Immunol. Today 9, 222-229 (1988).
11. Lynch, J. E., Choi, W. -B., Churchill, H. R. O., Volante, R. P., Reamer, R. A. and Ball, R. G., Asymmetric synthesis of CD840 by Jacobsen Epoxidation. An usual Syn selective reduction of an epoxide. J. Org. Chem., 62, 9223-9228 (1997).
12. Marivet, M. C., Bourguignon, J. -J., Lugnier, C., Mann, A., Stoclet, J. -C. and Wermuth, C., Inhibition of cyclic adenosine-3′,5′-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogues. J. Med. Chem., 32, 1450-1457 (1989).
13. Nicholson, C., Challis, R. and Shakio, M., Differential modulation of tissue function and therapeutic potential of selective inhibitors of cyclic nucleotide phosphodiesterase isoenzymes. Trends Pharmacol. Sci., 12, 19-27 (1991).
14. Schmiechen, R., Schneider, H. H. and Watchtel, H., Close correlation between behavioral response and binding in vivo for inhibitors of the rolipram-sensitive phosphodiesterase. Psychopharmacology, 102, 17-20 (1990).
15. Torphy, T. J. and Undem, B. J., Phosphodiesterase inhibitors: New opportunities for the treatment of asthma. Thorax 46, 512-523 (1991).
16. Smellie, A., Teig, S. L. and Towbin, P., "Poling: Promoting Conformational Coverage". J. Comp. Chem., 16, 171-187 (1995).
17. Weishaar, R. E., Cain, M. H. and Bristol, J. A., A new generation of phosphodiesterase inhibitors: multiple molecular forms of phosphodiesterase and the potential for drug selectivity. J. Med. Chem., 28, 537-545 (1985).