Skip to main content
Log in

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

  • Research Articles
  • Medicinal Chemistry
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

New series of catechol ether type derivatives5, 6 have been synthesized and applied to biological test. Even though it is a preliminary data, some of our target molecules show the promising result against PDE IV inhibition. SAR and biological studies with synthetic compounds will be discussed in detail.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References Cited

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    PubMed  CAS  Google Scholar 

  • Beavo, J. A., Conti, M. and Heaslip, R. J., Multiple cyclic nucleotide phosphodiesterases.Mol. Pharmacol., 46, 399–405 (1994).

    PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • Cohan, V. L., Showell, H. J., Pettipher, E. R., Fisher, D. A., Pazzoles, C. J., Watson, J. W., Turner, C. R. and Cheng, J. B.,In vitro pharmacology of the novel type IV phosphodiesterase (PDEIV) inhibitor, CP-80,633.J. Allergy Clin. Immunol., 95, 350 (1995) [Abstract].

    Google Scholar 

  • Cortijo, J., Bou, J., Beleta, J., Cardelus, I., Llenas, J., Motciool, E. and Gristwood, R. W., Investigation into the role of phosphodiesterase IV in bronchorelaxation, including studies with human bronchus.Br. J. Pharmacol., 108, 562–56 (1993).

    PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • Holbrook, M., Gozzard, N., James, T., Higgs, G. and Hughes, B., Inhibition of bronchospasm and ozone-induced airway hyperresponsiveness in the guineapig by CDP840, a novel phosphodiesterase type 4 inhibitor.Br. J. Pharmacol., 118, 1192–1200 (1996).

    PubMed  CAS  Google Scholar 

  • Kammer, G. M., The adenylate cyclase-cAMP-protein kinase pathway and regulation of immune response.Immunol. Today 9, 222–229 (1988).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • Schmiechen, R., Schneider, H. H. and Watchtel, H., Close correlation between behavioral response and bindingin vivo for inhibitors of the rolipram-sensitive phosphodiesterase.Psychopharmacology, 102, 17–20 (1990).

    Article  PubMed  CAS  Google Scholar 

  • Torphy, T. J. and Undem, B. J., Phosphodiesterase inhibitors: New opportunities for the treatment of asthma.Thorax 46, 512–523 (1991).

    Article  PubMed  CAS  Google Scholar 

  • Smellie, A., Teig, S. L. and Towbin, P., “Poling: Promoting Conformational Coverage”.J. Comp. Chem., 16, 171–187 (1995).

    Article  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Chung K. Rhee.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rhee, C.K., Kim, J.H., Sub, BC. et al. Synthesis and biological studies of catechol ether type derivatives as potential phosphodiesterase (PDE) IV inhibitors. Arch Pharm Res 22, 202–207 (1999). https://doi.org/10.1007/BF02976547

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02976547

Key words

Navigation