Synthesis and anxiolytic activity of 1-phenyl-2-(4-aryl-1,3,4,5- tetrahydropyrido[2,3-b][1,4]diazepin-2-ylidene)-ethanone

Pharmazie

Volumn 61, Issue 6, 2006, Pages 517-521

  Liszkiewicz, H ^a   Kowalska, M W ^b   Rutkowska, M ^a   Gliniak, H ^a  

^a WROCLAW MEDICAL UNIVERSITY   (Poland)

^b UNIVERSITY OF WROC AW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 2 (4 [3 BROMO 4,5 DIMETHOXYPHENYL] 1,3,4,5 TETRAHYDROPYRIDOL[2,3 B][1,4]DIAZEPIN 2 YLIDENE)ETHANONE; 1 PHENYL 2 (4 [4 BROMOPHENYL] 1,3,4,5 TETRAHYDROPYRIDOL[2,3 B][1,4]DIAZEPIN 2 YLIDENE)ETHANONE; 1 PHENYL 2 (4 [4 CHLOROPHENYL] 1,3,4,5 TETRAHYDROPYRIDOL[2,3 B][1,4]DIAZEPIN 2 YLIDENE)ETHANONE; 1 PHENYL 2 (4 [4 TRIFLUOROMETHYLPHENYL] 1,3,4,5 TETRAHYDROPYRIDOL[2,3 B][1,4]DIAZEPIN 2 YLIDENE)ETHANONE; 1 PHENYL 2 (4 PHENYL 1,3,4,5 TETRAHYDROPYRIDOL[2,3 B][1,4]DIAZEPIN 2 YLIDENE)ETHANONE; 1 PHENYL 2 [4 ARYL 1,3,4,5 TETRAHYDROPYRIDO(2,3 B)(1,4)DIAZEPIN 2 YLIDENE)ETHANONE; 2,3 DIAMINOPYRIDINE; ALDEHYDE; AMINOPYRIDINE; BENZALDEHYDE DERIVATIVE; BENZOYLACETONE; DIAZEPINE DERIVATIVE; FUNCTIONAL GROUP; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; MALE; MOUSE; NONHUMAN; POLYMERIZATION; TRANQUILIZING ACTIVITY;

ANIMALS; ANTI-ANXIETY AGENTS; ANXIETY; AZEPINES; BEHAVIOR, ANIMAL; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICE; MICE, INBRED BALB C;

EID: 33745609560     PISSN: 00317144     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. Bott G, Field LD, Sternhell S (1980) Steric effects. A study of a rationally designed system. J Am Chem Soc 102: 5618-5626.
2. Carmine AA, Broaden RN (1985) Pirenzepine. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy in peptic ulcer diseases and other allied diseases. Drugs 30: 85-126.
3. Costall B, Jones BJ, Kelly ME, Naylor RJ, Tomkinks DM (1989) Exploration of mice in a black and white test box: Validation as a model of anxiety. Pharmacol Biochem Behav 32: 777-785.
4. Hargrawe KD, Proudfoot JR, Grozinger KG, Cullen E, Kapadia SR, Patel UR, Fuchs VU, Mauldin SC, Vitous J, Behnke ML, Klunder JM, Pal K, Skiles JW, McNail DW, Rose JM, Chow GC, Skoog MT, Wu JC, Schmidt G, Engel WW, Eberlein WG, Saboe TD, Campbell SJ, Rosenthal AS, Adams J (1991) Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 1. Tricyclic pyridobenzo- and dipyridodiazepinones. J Med Chem 34: 2231-2241.
5. Honigfeld G (1996) The clozapine national registry system: forty years of risk management. J Clin Psychiatry Monogr 14: 29-32.
6. Laatikainen R, Kolehmainen E (1985) A detailed INDO/FPT level study on the transmission pathways of the side chain α-proton long-range spin-spin couplings in styrene, toluene, naphthalene, and some other simple aromatics. A strategy. J Magn Reson 65: 89-99.
7. 2A) receptors. J Med Chem 45: 5136-5149.
8. Link A, Zaharevitz DW, Kunick C (1999) Antitumor pyrido[3,2-d][1] benzazepines: synthesis and in vitro activity of thiophene analogs. Pharmazie 54: 163-166.
9. Liszkiewicz H, Głowiak T, Kowalska MW, Rutkowska M, Szela̧g A, Barczyńska J, Kȩdzierska-Goździk L, Blaszczyk F, Dziewiszek W (1999) Synthesis and pharmacological properties of new derivatives of 2-amino-5-(2-amino-3-pyridyl)-1,3,4-oxadiazole. Polish J Chem 73: 321-332.
10. Liszkiewicz H, Kowalska MW, Głowiak T, Wietrzyk J, Opolski A (2002) Synthesis and antiproliferative activity in vitro of 1-phenyl-2-(4-aryl- 1,3,4,5-tetrahydropyrido[2,3-b][1,4]diazepin-2-ylidene)ethanone. Part I. Polish J Chem 76: 1607-1616.
11. Liszkiewicz H, Nawrocka W, Rutkowska M (2005) Nowa pochodna pirydo[2,3-b]-[1,4]diazepiny i sposób jej wyrwarzania. Biul Urz Pat 9(818): 56 A1 363208.
12. Litchfield JT, Wilcoxon F (1949) A simplified method of evaluating dose-effect experiments. J Pharmacol Exp Ther 96: 99-114.
13. Malik F, Hassan M, Rosenbaum D, Duddeck H (1989) NMR Spectra and conformational analysis of substituted 1,3,4,5-tetrahydro-2H-1,5-benzodiazepin- 2-one derivatives. Magn Reson Chem 27: 391-395.
14. Nawojski A, Liszkiewicz H, Nawrocka W, Ernest K, Szymańska-Kosmala M (1983) Synthesis and pharmacological investigations of derivatives 6-azabenzodiazepines. Pol J Pharmacol Pharm 35: 77-85.
15. Ojima I, Kuduk SD, Slater JC, Gimi RH, Sun CM (1996) Syntheses of new fluorine-containing taxoids by means of β-lactam synthon method. Tetrahedron 52: 209-224.
16. O'Neil IA, Thompson S, Kalindjian B, Jenkins TC (2003) The synthesis and biological activity of C2-fluorinated pyrrolo[2,1-e][1,4]benzodiazepines. Tetrahedron Lett 44: 7809-7812.
17. Proudfoot JR, Patel UR, Kapadia SR, Hargrave KD (1995) Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 3. Dipyrido[2,3-b:2′,3′-e]diayepinones. J Med Chem 38: 1406-1410.
18. Pu Yu M, Torok DS, Ziffer H, Pan X-Q, Meshnick SR (1995) Synthesis and antimarial activities of several fluorinated artemisin derivatives. J Med Chem 38: 4120-4124.
19. Saczewski F, Kobierska E, Petrusewicz J, Gendzwill A, Gdaniec M (2003) Synthesis and structure of novel 2,3,5,6-tetrahydro-1H-imidazo[2,1-b][1,3,5] benzotriazepines with vasocontractile activity in rabbit aortic rings. Farmaco 58: 1171-1178.
20. Stará IG, Starý I, Tichý M, Závada J, Hanuś (1994) Stereochemical dichotomy in the Stevens rearrangement of axially twisted dihydroazepinium and dihydrothie-pinium salts. A novel enantioselective synthesis of pentahelicene. J Am Chem Soc 116: 5084-5088.
21. Woolard FX, Paetsch J, Ellman JA (1997) A silicon linker for direct loading of aromatic compounds to supports. Traceless synthesis of pyridine-based tricyclics. J Org Chem 62: 6102-6103.
22. Zhao CL, Uetrecht JP (1995) Clozapine is oxidized by activated human neutrophils to a reactive nitrenium ion that irreversibly binds to the cells. J Pharmacol Exp Ther 275: 1476-1483.
23. Zhang W, Koehler KF, Harris B, Skolnick P, Cook JM (1994) Synthesis of benzofused benzodiazepines employed as probes of the agonist pharmacophore of benzodiazepine receptors. J Med Chem 37: 745-757.