Synthesis and biological evaluation of novel azetidine derivatives as dopamine antagonist

Medicinal Chemistry Research

Volumn 22, Issue 12, 2013, Pages 5982-5989

  Metkar, Shashikant D ^a   Bhatia, Manish S ^b   Desai, Uday V ^a  

^a SHIVAJI UNIVERSITY   (India)

^b BHARATI VIDYAPEETH COLLEGE OF PHARMACY   (India)

Author keywords

Azetidine; Benzhydrylamines; D2, D4 antagonist; Epichlorohydrin

Indexed keywords

3 AMINO 1 BENZHYDRYL AZETIDINE; 3 HYDROXY 1 BENZHYDRYL AZETIDINE; AZETIDINE DERIVATIVE; DOPAMINE 2 RECEPTOR; DOPAMINE 4 RECEPTOR; DOPAMINE RECEPTOR BLOCKING AGENT; N (1 BENZHYDRYL AZETIDIN 3YL METHANESULFONATE; N (1 BENZHYDRYL AZETIDIN 3YL) 2 BROMO BENZAMIDE; N (1 BENZHYDRYL AZETIDIN 3YL) 2 CHLORO BENZAMIDE; N (1 BENZHYDRYL AZETIDIN 3YL) 2 METHOXY BENZAMIDE; N (1 BENZHYDRYL AZETIDIN 3YL) 2 METHYL BENZAMIDE; N (1 BENZHYDRYL AZETIDIN 3YL) 2 NITRO BENZAMIDE; N (1 BENZHYDRYL AZETIDIN 3YL) 4 BROMO BENZAMIDE; N (1 BENZHYDRYL AZETIDIN 3YL) 4 IODO BENZAMIDE; N (1 BENZHYDRYL AZETIDIN 3YL) 4 NITRO BENZAMIDE; N (1 ENZHYDRYL AZETIDIN 3YL) 2,4 DICHLORO BENZAMIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BIOLOGICAL ACTIVITY; CATALEPSY; CONTROLLED STUDY; DOPAMINERGIC ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR DOCKING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RAT; STRUCTURE ACTIVITY RELATION;

EID: 84886087636     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0579-3     Document Type: Article

References (19)

1. 7 antagonist: relevance for antidepressant actions in vivo. Psychopharmacology 205:119-128. doi: 10.1007/S00213-009-1521-8
2. Aoyana Y, Uenaka M, Kji M, Tanaka M, Konoike T, Havasaki KY, Naya N, Nakajima M (2001) Design, synthesis and pharmacological evaluation of 3-benzylazetidine-2-one-based human chymase inhibitors. Bioorg Med Chem 9:3065-3075. doi: 10.1016/S0968-0896(01)00209-7
3. Barth P, Fritschi H, Nystroem JE, Pfenninger WO (1997) 9702241
4. Faust MR, Hofner G, Pabel J, Wanner KT (2010) Azetidine derivatives as novel γ-aminobutyric acid uptake inhibitors: Synthesis, biological evaluation, and structure activity relationship. Eur J Med Chem 45:2453-2466. doi: 10.1016/j.ejmech.2010.02.029
5. Heindl C, Hubner H, Gmeniner P (2003) Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives. Tetrahedron Asymmetry 14:3141-3152. doi: 10.1016/j.tetasy.2003.08.019
6. Isoda T, Yamanura I, Tamal S, Kumagal T (2006) A Practical and Facile synthesis of azetidine derivatives for oral carbapenem, L-084. Chem Pharm Bull 54:1408-1411. doi: 10.1002/chin.200713207
7. 4 receptor. J Med Chem 39:1941-1942. doi: 10.1021/jm9600712
8. Kvarebo L, Werder M, Hauser H, Carreira EM (2005) Synthesis and in vitro evaluation of inhibitors of intestinal cholesterol absorption. J Med Chem 48:6035-6053. doi: 10.1021/jm050422p
9. Melloni P, Della A, Meroni M, Ambrosini A, Rossi AC (1979) Azetidine derivatives of tricyclic antidepressant agents. J Med Chem 22:183-191. doi: 10.1021/jm00188a012
10. Metzner L, Kalbitz J, Brandsch M (2004) Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1. J Pharmacol Exp Ther 309:28-35. doi: 10.1124/jpet.103.059014
11. Morimoto A, Okutani T, Masuda K (1973) Preparation of enantiopure norbornane ligands bearing both (2S,3S)-bis(phosphinomethyl) and 7-syn-oxygen functional groups and an application to rhodium-catalyzed asymmetric hydrogenation. Chem Pharm Bull 21:228-231
12. O'Dowd H, Lewis JG, Trias J, Asano R, Blias J, Lopez SL, Park CK, Wu C, Gordeey MF (2008) Novel antibacterial azetidine lincosamides. Bioorg Med Chem Lett 18:2645-2648. doi: 10.1016/j2008.03.032
13. Okuyama S, Imagawa Y, Ogawa S, Araki H, Ajima A, Tanaka M, Muramatsu M, Nakazato A, Yamaguchi K, Yoshida M, Otomo S (1993) NE-100, A Novel sigma receptor ligand: in vivo tests. Life Sci 53:285-290. doi: org/10.1016/0024- 3205(93)90588-T
14. Orr AF (1986) Shell Oil Company, US Patent No. 4620866
15. Pettersson M, Campbell BM, Dounay AB, Gray DL, Xie L, O'Donnell DJ, Stratman NC, Zoski K, Drummond E, Bora G, Probert A, Hisman T (2011) Design, synthesis, and pharmacological evaluation of azetedine and pyrrolidine derivatives as dual norepinephrine reuptake inhibitors and 5-HT1A partial agonists. Bioorg Med Chem Lett 21:865-868
16. Rajasekaran A, Periasamy M, Venkatesan S (2010) Synthesis, characterization and biological activity of some novel azetidinones. J Dev Biol Tissue Eng 2:5-13
17. Ratomponirina C, Gobaille S, Hode Y, Kemmel V, Maitre M (2003) Sulpiride, but not haloperidol, up-regulates γ-hydroxybutyrate receptors in vivo and in cultured cells. Eur J Pharmacol 346:331-337. doi: org/10.1016/S0014-2999(98) 00068-5
18. Singh T, Srivastav VK, Saxena KK, Goel SL, Kumar A (2006) Synthesis of new thiazolylthiazolidinylbenzothiazoles and thiazolylazetidinylbenzothiazoles as potential insecticidal, antifungal, and antibacterial agents. Arch Pharm 339:466-472. doi: 10.1002/ardp.200500265
19. Woodhead SJ, Downham R, Hamlett C, Howard S, Sore HF, Verdonk ML, Walker DW, Luke RWA (2006) WO2006136830