Synthesis and pharmacological activity of 2-(substituted)-3-{2-[(4-phenyl- 4-cyano)piperidino]ethyl}-1,3-thiazolidin-4-ones

Chemical Biology and Drug Design

Volumn 67, Issue 6, 2006, Pages 432-436

  Mazzoni, Orazio ^a   Di Bosco, Antonio Mazzella ^a   Grieco, Paolo ^a   Novellino, Ettore ^a   Bertamino, Alessia ^a   Borrelli, Francesca ^a   Capasso, Raffaele ^a   Diurno, Maria Vittoria ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

1,3 thiazolidin 4 ones derivatives; Antidiarrhoeal activity; Thiazolidinones

Indexed keywords

2 (4 METHYLPHENYL) 3 [2 [(4 PHENYL 4 CYANO)PIPERIDINO]ETHYL] 1,3 THIAZOLIDIN 4 ONE; 2 (4 NITROPHENYL) 3 [2 [(4 PHENYL 4 CYANO)PIPERIDINO]ETHYL] 1,3 THIAZOLIDIN 4 ONE; 2 (INDOL 3 YL) 3 [2 [(4 PHENYL 4 CYANO)PIPERIDINO]ETHYL] 1,3 THIAZOLIDIN 4 ONE; 2 (NAPHTHYL 2 YL) 3 [2 [4 (PHENYL 4 CYANO)PIPERIDINO]ETHYL] 1,3 THIAZOLIDIN 4 ONE; 2 PHENYL 3 [2 [(4 PHENYL 4 CYANO)PIPERIDINO]ETHYL] 1,3 THIAZOLIDIN 4 ONE; 2,4 THIAZOLIDINEDIONE DERIVATIVE; ANTIDIARRHEAL AGENT; CASTOR OIL; LOPERAMIDE; NALOXONE; OPIATE RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DIARRHEA; DOSE RESPONSE; DRUG ACTIVITY; DRUG MEGADOSE; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; LD 50; MOUSE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; ANTIDIARRHEALS; CASTOR OIL; DIARRHEA; LOPERAMIDE; MICE; MODELS, MOLECULAR; NALOXONE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLIDINEDIONES;

EID: 33746115697     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2006.00399.x     Document Type: Article

References (21)

1. Coupar I.M. (1987) Opioid action on the intestine: the importance of the intestinal mucosa. Life Sci;41:917-925.
2. Van Neuten J.M., Janssen P.A., Fontaine J. (1974) Loperamide (R-18533), a novel type of antidiarrheal agent: Part 3. In vitro studies on the peristaltic reflex and other experiments on isolated tissues. Arzeinmittelforschung;24:1641- 1645.
3. Awouters F., Niemegeers C.J., Janssen P.A. (1983) Pharmacology of antidiarrheal drugs. Annu Rev Pharmacol Toxicol;23:279-301.
4. Bueno L., Fioramonti J. (1988) Action of opiates on gastrointestinal function. Baillieres Clin Gastroenterol:2:123-139.
5. Bradwshaw J.M., Harvey R.F. (1982) Antidiarrhoeal agents. Clinical pharmacology and therapeutic use. Drugs;24:440-451.
6. Gutstein H.B., Akil H. (2003) Analgesici oppioidi, Jafri S. and Pasricha P. J. Terapia della diarrea, della stipsi e delle malattie infiammatorie intestinali. In: Hardman J.G., Limbird L.E., Goodman Gilman A., editors. Goodman & Gilman's The Pharmacological Basis of Therapeutics, 10th edn. New York, USA: Mc-Graw Hill;p. 566-573, 985-989.
7. Sadeque A.J., Wandel C., He H., Shah S., Wood A.J. (2000) Increased drug delivery to the brain by P-glycoprotein inhibition. Clin Pharmacol Ther;68:231-237.
8. Diurno M.V., Izzo A.A., Mazzoni O., Bolognese A., Capasso F. (1996) Antidiarrhoeal activity of new thiazolidinones related to Loperamide. J Pharm Pharmacol;48:760-762.
9. G-Nitro-L-arginine methyl ester modulates intestinal secretion and motility produced by carbachol. Eur J Pharmacol;271:31-35.
10. Niemeggers C.L.E., Lenaerts F.M., Janssen P.A.J. (1974) Loperamide (R-18533), a novel type of antidiarrheal agent: Part 1. In vivo oral pharmacology and acute toxicity. Comparison with morphine, codeine, diphenoxylate and difenoxine. Arzeinmittelforschung;24:1633-1636.
11. Subramanian G., Paterlini M.G., Portoghese P.S., Ferguson D.M. (2000) Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor. J Med Chem;43:381-391.
12. Micovic I.V., Ivanovic M.D., Vuckovic S.M., Prostran M.S., Dosen-Micovic L., Kiricojevic V.D. (2000) The synthesis and preliminary pharmacological evaluation of 4-methyl fentanyl. Bioorg Med Chem Lett;10:2011-2014.
13. Kromer W. (1988) Endogenous and exogenous opioids in the control of gastrointestinal motility and secretion. Pharm Rev;40:121-162.
14. Wüster M., Herz A. (1978) Opiate agonist action of antidiarrheal agents in vitro and in vivo - findings in support for selective action. Naunyn Schmiedebergs Arch Pharmacol;301:187-194.
15. Diurno M.V., Mazzoni O., Calignano A., Giordano F., Bolognese A. (1992) Synthesis and antihistaminic activity of some thiazolidin-4-ones. J Med Chem;35:2910-2912.
16. Tallarida R.J., Murray R.B. (1986) Manual of Pharmacological Calculations with Computer Programs. New York, USA: Springer-Verlag.
17. Brünger A.T., Kuriyan J., Karplus M. (1987) Crystallographic R factor refinement by molecular dynamics. Science;235:458-460.
18. Nilges M., Clore G.M., Gronenborn A.M. (1988) Determination of three-dimensional structures of proteins from interproton distance data by dynamical simulated annealing from a random array of atoms. Circumventing problems associated with folding. FEBS Lett;239:129-136.
19. Havel T.F. (1991) An evaluation of computational strategies for use in the determination of protein structure from distance constraints obtained by nuclear magnetic resonance. Prog Biophys Mol Biol;56:43-78.
20. Dauber-Osguthorpe P., Roberts V.A., Osguthorpe D.J., Wolff J., Genest M., Hagler A.T. (1988) Structure and energetics of ligand binding to proteins: Escherichia coli dihydrofolate reductase-trimethoprim, a drug-receptor system. Proteins;4:31-47.
21. Allinger N.L., Yuh Y.H., Lii J.H. (1989) Molecular mechanics. The MM3 force field for hydrocarbons. J Am Chem Soc;111:8551-8566.