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Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine.

Publication ,  Journal Article
Kaminski, JJ; Carruthers, NI; Wong, SC; Chan, TM; Billah, MM; Tozzi, S; McPhail, AT
Published in: Bioorganic & medicinal chemistry
July 1999

Following the discovery of the first dual antagonist of platelet-activating factor (PAF) and histamine, 1-acetyl-4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin- 11-ylidene)piperidine, Sch 37370, 1, a related series of structures, exemplified by (+/-)-1-acetyl-4-(8-chloro-5,6-dihydro-11H-benzo[5,6]-cyclohepta[1,2-b] pyridin-11-yl)piperazine, Sch 40338, 2, were prepared. Interestingly, the compounds exhibited a parallel structure antiallergy activity relationship, suggesting that the two series may adopt a common conformation at the PAF receptor. Conformational analysis led to a proposal for this bioactive conformation accessible to both series. The synthesis of novel conformationally constrained analogues that might mimic the proposed bioactive conformation of these compounds, and the evaluation of their in vitro antiallergy activity form the subject matter of this report.

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Published In

Bioorganic & medicinal chemistry

DOI

EISSN

1464-3391

ISSN

0968-0896

Publication Date

July 1999

Volume

7

Issue

7

Start / End Page

1413 / 1423

Related Subject Headings

  • Structure-Activity Relationship
  • Stereoisomerism
  • Receptors, Histamine H1
  • Rats
  • Pyridines
  • Platelet Aggregation Inhibitors
  • Platelet Aggregation
  • Platelet Activating Factor
  • Piperidines
  • Piperazines
 

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Kaminski, J. J., Carruthers, N. I., Wong, S. C., Chan, T. M., Billah, M. M., Tozzi, S., & McPhail, A. T. (1999). Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine. Bioorganic & Medicinal Chemistry, 7(7), 1413–1423. https://doi.org/10.1016/s0968-0896(99)00075-9
Kaminski, J. J., N. I. Carruthers, S. C. Wong, T. M. Chan, M. M. Billah, S. Tozzi, and A. T. McPhail. “Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine.Bioorganic & Medicinal Chemistry 7, no. 7 (July 1999): 1413–23. https://doi.org/10.1016/s0968-0896(99)00075-9.
Kaminski JJ, Carruthers NI, Wong SC, Chan TM, Billah MM, Tozzi S, et al. Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine. Bioorganic & medicinal chemistry. 1999 Jul;7(7):1413–23.
Kaminski, J. J., et al. “Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine.Bioorganic & Medicinal Chemistry, vol. 7, no. 7, July 1999, pp. 1413–23. Epmc, doi:10.1016/s0968-0896(99)00075-9.
Kaminski JJ, Carruthers NI, Wong SC, Chan TM, Billah MM, Tozzi S, McPhail AT. Conformational considerations in the design of dual antagonists of platelet-activating factor (PAF) and histamine. Bioorganic & medicinal chemistry. 1999 Jul;7(7):1413–1423.
Journal cover image

Published In

Bioorganic & medicinal chemistry

DOI

EISSN

1464-3391

ISSN

0968-0896

Publication Date

July 1999

Volume

7

Issue

7

Start / End Page

1413 / 1423

Related Subject Headings

  • Structure-Activity Relationship
  • Stereoisomerism
  • Receptors, Histamine H1
  • Rats
  • Pyridines
  • Platelet Aggregation Inhibitors
  • Platelet Aggregation
  • Platelet Activating Factor
  • Piperidines
  • Piperazines