Synthesis and pharmacological characterization of enantiomerically pure muscarinic agonists: Difluoromuscarines

Journal of Medicinal Chemistry

Volumn 40, Issue 7, 1997, Pages 1099-1103

  Angeli, Piero ^a   Cantalamessa, Franco ^a   Cavagna, Roberto ^a   Conti, Paola ^b   De Amici, Marco ^b   De Micheli, Carlo ^b   Gamba, Anna ^c   Marucci, Gabriella ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

^c UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 [(DIMETHYLAMINO)METHYL] 4,4 DIFLUORO 5 METHYLTETRAHYDROFURAN METHIODIDE; MUSCARINE DERIVATIVE; MUSCARINIC AGENT; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLADDER CONTRACTION; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENANTIOMER; GUINEA PIG; HEART MUSCLE CONTRACTILE FORCE; HEART RATE; HEMODYNAMICS; ILEUM CONTRACTION; NONHUMAN; RAT; RECEPTOR AFFINITY; STEREOSPECIFICITY;

ANIMALS; GUINEA PIGS; HEART ATRIA; ILEUM; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MUSCARINE; MUSCARINIC AGONISTS; RATS; RECEPTORS, MUSCARINIC; STEREOISOMERISM; URINARY BLADDER;

EID: 0030965572     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960742w     Document Type: Article

References (15)

1. De Amici, M.; Dallanoce, C.; De Micheli, C.; Grana, E.; Dondi, G.; Ladinsky, H.; Schiavi, G. B.; Zonta, F. Synthesis and pharmacological investigation of stereoisomeric muscarines. Chirality 1992, 4, 230-239.
2. De Amici, M.; Dallanoce, C.; De Micheli, C.; Grana, E.; Barbieri, A.; Ladinsky, H.; Schiavi, G. B.; Zonta, F. Synthesis and pharmacological investigation of the enantiomers of muscarone and allomuscarone. J. Med. Chem. 1992, 35, 1915-1920.
3. De Amici, M.; De Micheli, C.; Gianferrara, T.; Grana, E.; Zonta, F.; Ladinsky, H.; Schiavi, G. B. Synthesis and muscarinic activity of the chiral forms of methylenemusearones. Il Farmaco 1993, 48, 1349-1357.
4. Angeli, P. Pentatomic cyclic agonists and muscarinic receptors: a 20 years review. Il Farmaco 1995, 9, 565-577 and references cited therein.
5. Bravo, P.; Resnati, G.; Angeli, P.; Frigerio, M.; Viani, F.; Arnone, A.; Marucci, G.; Cantalamessa, F. Synthesis and pharmacological evaluation of enantiomerically pure 4-deoxy-4-fluoromuscarines. J. Med. Chem. 1992, 35, 3102-3110.
6. Hudlicky, M. Fluorination with diethylaminosulfur trifluoride and related aminofluorosulfuranes. Org. React. 1988, 35, 513-637.
7. Wilkinson, J. A. Recent Advances in the Selective Formation of the Carbon-Fluorine Bond. Chem. Rev. 1992, 92, 505-519.
8. Angeli, P.; Brasili, L.; Giannella, M.; Gualtieri, F.; Picchio, M. T.; Teodori, E. Chiral muscarinic agonists possessing a 1,3-oxathiolane nucleus: enantio-and tissue-selectivity on isolated preparations of guinea-pig ileum and atria and of rat urinary bladder. Naunyn-Schmiedeberg's Arch. Pharmacol. 1988, 337, 241-245.
9. 2 muscarinic receptors in a modified pithed rat preparation. Naunyn-Schmiedeberg's Arch. Pharmacol. 1990, 342, 625-629.
10. Furchgott, R. F. The classifications of adrenoceptors. An evaluation from the standpoint of receptor theory. In Handbook of experimental pharmacology; Blaschko H., Muscholl E., Eds.; Springer: Berlin, Heidelberg New York, 1972; pp 283-335.
11. Angeli, P.; Brasili, L.; Giannella, M.; Gualtieri, F.; Pigini, M. Affinity and efficacy correlate with chemical structure more than potency does in a series of pentatomic cyclic muscarinic agonists. Br. J. Pharmacol. 1985, 85, 783-786.
12. 6 solution.
13. 6 solution.
14. Furchgott, R. F.; Bursztyn, P. Comparison of dissociation constants and of relative efficacies of selected agonists acting on parasympathetic receptors. Ann. N.Y. Acad. Sci. 1967, 144, 882-899.
15. Shipley, R. E.; Tilden, J. H. A pithed rat preparation suitable for assaying pressor substances. Proc. Soc. Exp. Biol. Med. 1947, 64, 453-455.