Novel oxotremorine-related heterocyclic derivatives: Synthesis and in vitro pharmacology at the muscarinic receptor subtypes

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 24, 2007, Pages 7626-7637

  Dallanoce, Clelia ^a   De Amici, Marco ^a   Barocelli, Elisabetta ^b   Bertoni, Simona ^b   Roth, Bryan L ^c   Ernsberger, Paul ^d   De Micheli, Carlo ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

^c UNIVERSITY OF NORTH CAROLINA   (United States)

^d CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

Binding assays; Cloned receptors; Functional tests; Muscarinic ligands; Muscarinic receptor subtypes; Oxotremorine related compounds

Indexed keywords

1 [4 (4,5 DIHYDROISAXAZOL 3 YLOXY)BUT 2 YN 1 YL]INDOLINE; 1 [4 (4,5 DIHYDROISAXAZOL 3 YLOXY)BUT 2 YN 1 YL]INDOLINE METHIODIDE; 1 [4 (4,5 DIHYDROISAXAZOL 3 YLOXY)BUT 2 YN 1 YL]PIPERIDINE METHIODIDE; 1 [4 (4,5 DIHYDROISAXAZOL 3 YLOXY)BUT 2 YN 1 YL]PIPERIDINE OXALATE; 2 (4 PIPERIDIN 1 YLBUT 2 YN 1 YL)ISOXAZOLIDIN 3 ONE; 2 (4 PIPERIDIN 1 YLBUT 2 YN 1 YL)ISOXAZOLIDIN 3 ONE METHIODIDE; 2 [4 (2,3 DIHYDRO 1H INDOL 1 YL)BUT 2 YN 1 YL)ISOXAZOLIDIN 3 ONE METHIODIDE; 2 [4 (3,4 DIHYDROISOQUINOLIN 2(1H)YL) BUT 2 YN 1 YL]ISOXAZOLIDIN 3 ONE OXALATE; 2 [4 (3,4 DIHYDROISOQUINOLIN 2(1H)YL)BUT 2 YN 1 YL)ISOXAZOLIDIN 3 ONE METHIODIDE; 2 [4 (4,5 DIHYDROISOXAZOL 3 YLOXY)BUT 2 YN 1 YL] 1,2,3,4 TETRAHYDROISOQUINOLINE METHIODIDE; 2 [4 (4,5 DIHYDROISOXAZOL 3 YLOXY)BUT 2 YN 1 YL] 1,2,3,4 TETRAHYDROISOQUINOLINE OXALATE; 2 [4 (8 AZABICYCLO[3.2.1]OCT 8 YL)BUT 2 YN 1 YL]ISOXAZOLIDIN 3 ONE; 5 METHYL 3 [(4 PYROLIDIN 1 YLBUT 2 YN 1 YL)OXY]ISOXAZOLE FUMARATE; 5 METHYL 3 [(4 PYRROLIDIN 1 YLBUT 2 YN 1 YL)OXY]ISOXAZOLE METHIODIDE; 5 PHENYL 3 [(4 PYROLIDIN 1 YLBUT 2 YN 1 YL)OXY]ISOXAZOLE FUMARATE; 5 PHENYL 3 [(4 PYRROLIDIN 1 YLBUT 2 YN 1 YL)OXY]ISOXAZOLE METHIODIDE; 8 [4 (4,5 DIHYDROISOXAZOL 3 YLOXY)BUT 2 YN 1 YL] 8 AZABICYCLO[3.2.1]OCTANE OXALATE; [4 [(3 CHLOROPHENYL)CARBAMOYLOXY] 2 BUTYNYL]TRIMETHYLAMMONIUM; BETHANECHOL; MUSCARINIC M1 RECEPTOR; MUSCARINIC M1 RECEPTOR AGONIST; MUSCARINIC M2 RECEPTOR; MUSCARINIC M2 RECEPTOR AGONIST; MUSCARINIC M3 RECEPTOR; N,N DIMETHYL 4 [(5 METHYLISOXAZOL 3 YL)OXY] BUT 2 YN 1 AMINE FUMARATE; N,N DIMETHYL 4 [(5 METHYLISOXAZOL 3 YL)OXY]BUT 2 YN 1 AMINE METHIODIDE; N,N DIMETHYL 4 [(5 PHENYLISOXAZOL 3 YL)OXY]BUT 2 YN 1 AMINE OXALATE; OXOTREMORINE DERIVATIVE; QUINUCLIDIN 3 ONE O [4 (ISOXAZOL 3 YLOXY)BUT 2 YN 1 YL]OXIME FUMARATE; QUINUCLIDIN 3 ONE O [4 (ISOXAZOL 3 YLOXY)BUT 2 YN 1 YL]OXIME METHIODIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CHO CELL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG DETERMINATION; DRUG EFFICACY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ELECTROSTIMULATION; FEMALE; IN VITRO STUDY; NONHUMAN; PROTEIN FUNCTION;

ANIMALS; CELLS, CULTURED; DRUG EVALUATION, PRECLINICAL; GUINEA PIGS; HETEROCYCLIC COMPOUNDS; HUMANS; LIGANDS; MOLECULAR STRUCTURE; MUSCARINIC AGONISTS; MUSCARINIC ANTAGONISTS; OXOTREMORINE; RABBITS; RECEPTORS, MUSCARINIC; RECOMBINANT PROTEINS;

EID: 35348901533     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.09.003     Document Type: Article

References (37)

1. Caulfield M.P. Pharmacol. Ther. 58 (1993) 319
2. Wess J. Crit. Rev. Neurobiol. 10 (1996) 69
3. Caulfield M.P., and Birdsall N.J.M. Pharmacol. Rev. 50 (1998) 279
4. Eglen R.M. Auton. Autacoid. Pharmacol. 26 (2006) 219
5. Levey A.I. Life Sci. 52 (1993) 441
6. Vilaro M.T., Mengod G., and Palacios J.M. Prog. Brain Res. 98 (1993) 95
7. Chelala J.L., Kilani A., Miller M.J., Martin R.J., and Ernsberger P. Pharmacol. Toxicol. 83 (1998) 200
8. Wess J. Annu. Rev. Pharmacol. Toxicol. 44 (2004) 423
9. Mulugeta E., Karlsson E., Islam A., Kalaria R., Mangat H., Winblad B., and Adem A. Brain Res. 960 (2003) 259
10. Sheardown M.J., Shannon H.E., Swedberg M.D., Suzdak P.D., Bymaster F.P., Olesen P.H., Mitch C.H., Ward J.S., and Sauerberg P. J. Pharmacol. Exp. Ther. 281 (1997) 868
11. Mulugeta E., El-Bakri N., Karlsson E., Elhassan A., and Adem A. Brain Res. 982 (2003) 284
12. Yamada M., Basile A.S., Fedorova I., Zhang W., Duttaroy A., Cui Y., Lamping K.G., Faraci F.M., Deng C.-X., and Wess J. Life Sci. 74 (2003) 345 and references cited therein
13. Eglen R.M., and Nahorski S.R. Br. J. Pharmacol. 130 (2000) 13
14. Power A.E. Curr. Med. Chem. 11 (2004) 987
15. Sur C., and Kinney G.G. Curr. Neuropharmacol. 3 (2005) 63
16. Felder C.C., Bymaster F.P., Ward J., and De-Lapp N. J. Med. Chem. 43 (2000) 4333 and references cited therein
17. De Amici M., De Micheli C., Grana E., Rodi R., Zonta F., and Santagostino-Barbone M.G. Eur. J. Med. Chem. 24 (1989) 171
18. De Amici M., Dallanoce C., De Micheli C., Grana E., Barbieri A., Ladinsky H., Schiavi G.B., and Zonta F. J. Med. Chem. 35 (1992) 1915
19. Angeli P., Cantalamessa F., Cavagna R., Conti P., De Amici M., De Micheli C., Gamba A., and Marucci G. J. Med. Chem. 40 (1997) 1099
20. Dallanoce C., Conti P., De Amici M., De Micheli C., Barocelli E., Chiavarini M., Ballabeni V., Bertoni S., and Impicciatore M. Bioorg. Med. Chem. 7 (1999) 1539 and references cited therein
21. Barocelli E., Ballabeni V., Bertoni S., Dallanoce C., De Amici M., De Micheli C., and Impicciatore M. Life Sci. 67 (2000) 717
22. De Amici M., Conti P., Fasoli E., Barocelli E., Ballabeni V., Bertoni S., Impicciatore M., Roth B.L., Ernsberger P., and De Micheli C. Farmaco 58 (2003) 739
23. Disingrini T., Muth M., Dallanoce C., Barocelli E., Bertoni S., Kellershohn K., Mohr K., De Amici M., and Holzgrabe U. J. Med. Chem. 49 (2006) 366
24. Barocelli E., Ballabeni V., Bertoni S., De Amici M., and Impicciatore M. Life Sci. 68 (2001) 1775
25. Sorensen U.S., Falch E., and Krogsgaard-Larsen P. J. Org. Chem. 65 (2000) 1003
26. Iwai I., and Nakamura N. Chem. Pharm. Bull. 14 (1966) 1277
27. Mitsunobu O. Synthesis 1 (1981) 1
28. Grochowski E., and Jurczak J. Synthesis (1976) 682
29. Xu R., Sim M.-K., and Go M.-L. J. Med. Chem. 41 (1998) 3220
30. 4 receptors:. Budriesi R., Cacciaguerra S., Di Toro R., Bolognesi M.L., Chiarini A., Minarini A., Rosini M., Spampinato S., Tumiatti V., Melchiorre C. Br. J. Pharmacol. 132 (2001) 1099
31. Gómez C., Huerta F.F., Pastor I.M., and Yus M. Tetrahedron 53 (1997) 17201
32. Daly J.W., Gupta T.H., Padgett W.L., and Pei X.-F. J. Med. Chem. 43 (2000) 2514
33. Furchgott R.F., and Bursztyn P. Ann. N. Y. Acad. Sci. 144 (1967) 882
34. McKay D. Br. J. Pharmacol. 26 (1966) 9
35. Cheng Y.-C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
36. Eltze M. Eur. J. Pharmacol. 151 (1988) 205
37. Van Rossum J.M. Arch. Int. Pharmacodyn. Ther. 143 (1963) 299