Evaluation of selective human MAO inhibitory activities of some novel pyrazoline derivatives

Journal of Neural Transmission

Volumn 120, Issue 6, 2013, Pages 863-873

  Salgin Gökşen, Umut ^a,b   Yabanoǧlu Çiftçi, Samiye ^a   Ercan, Ayşe ^a   Yelekçi, Kemal ^c   Uçar, Gülberk ^a   Gökhan Kelekçi, Nesrin ^a  

^a HACETTEPE UNIVERSITY   (Turkey)

^b Turkish Medicines and Medical Devices Agency Analyses and Control Laboratories   (Turkey)

^c KADIR HAS UNIVERSITY   (Turkey)

Author keywords

2 Benzoxazolinone; 2 Pyrazoline; Chalcone; Molecular docking; Monoamine oxidase inhibitory activity

Indexed keywords

1 [2 [(5 METHYL CHLORO) 2 BENZOXAZOLINONE 3 YL] ACETYL] 3,5 DIARYL 4,5 DIHYDRO 1H PYRAZOLE DERIVATIVE; AMINE OXIDASE (FLAVIN CONTAINING); CLORGYLINE; MOCLOBEMIDE; MONOAMINE OXIDASE A INHIBITOR; MONOAMINE OXIDASE B INHIBITOR; PARGYLINE; PYRAZOLINE DERIVATIVE; SELEGILINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; ENZYME INHIBITION; IN VITRO STUDY; INFRARED SPECTROSCOPY; MOLECULAR DOCKING; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

BENZOXAZOLES; CHALCONE; HUMANS; MODELS, MOLECULAR; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TRITIUM;

EID: 84878712115     PISSN: 03009564     EISSN: 14351463     Source Type: Journal    
DOI: 10.1007/s00702-013-0980-6     Document Type: Article

References (47)

1. Anderson MC, Hasan F, McCrodden JM, Tipton KF (1993) Monoamine oxidase inhibitors and the cheese effect. Neurochem Res 18:1145-1149
2. Bilgin AA, Palaska E, Sunal R (1993) Studies on the synthesis and antidepressant activity of Some 1-thiocarbamoyl-3,5-diphenyl-2-pyrazolines. Arzneimittel-Forsch 43:1041-1044
3. Binda C, Wang J, Pisani L, Caccia C, Carotti A, Salvati P, Edmondson DE, Mattevi A (2007) Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: safinamide and coumarin analogs. J Med Chem 50:5848-5852
4. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
5. ÇakIr B, Daǧ Ö, YIldIrIm E, Erol K, Şahin MF (2001) Synthesis and anticonvulsant activity of some hydrazones of 2[(3H)-oxobenzoxazolin-3-yl-aceto]hydrazide. J Fac Pharm Gazi 18:99-106
6. Chen SQ, Zhang YC, Liu FM (2011) Synthesis and spectral characterization of some new thiazolyl-pyrazolines bearing 1,2,4-triazole moiety. Phosphorus Sulfur 186:319-325
7. Chimenti F, Bolasco A, Manna F, Secci D, Chimenti P et al (2004) Synthesis and selective inhibitory activity of 1-acetyl-3,5-diphenyl-4,5- dihydro-(1H)-pyrazole derivatives against monoamine oxidase. J Med Chem 47:2071-2074
8. Chimenti F, Maccioni E, Secci D, Bolasco A, Chimenti P, Granese A et al (2005) Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)- pyrazole derivatives. J Med Chem 48:7113-7122
9. Chimenti F, Bolasco A, Manna F, Secci D, Chimenti P, Granese A, Befani O, Turini P, Alcaro S, Ortuso F (2006a) Synthesis and molecular modelling of novel substituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase-A inhibitors. Chem Biol Drug Des 67:206-214
10. Chimenti F, Bolasco A, Manna F, Secci D, Chimenti P, Granesea A, Befani O, Turini P, Cirilli R et al (2006b) Synthesis, biological evaluation and 3D-QSAR of 1,3,5-trisubstituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase A inhibitors. Curr Med Chem 13:1411-1428
11. Chimenti F, Fioravanti R, Bolasco A, Manna F, Chimenti P et al (2007) Monoamine oxidase isoform-dependent tautomeric influence in the recognition of 3,5-diaryl pyrazole Inhibitors. J Med Chem 50:425-428
12. Chimenti F, Fioravanti R, Bolasco A, Manna F, Chimenti P et al (2008a) Synthesis, molecular modeling studies and selective inhibitory activity against MAO of N1-propanoyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives. Eur J Med Chem 43:2262-2267
13. Chimenti F, Maccioni E, Secci D, Bolasco A, Chimenti P et al (2008b) Synthesis, stereochemical identification, and selective inhibitory activity against human monoamine oxidase-B of 2-methylcyclohexylidene-(4-arylthiazol-2- yl)hydrazones. J Med Chem 51:4874-4880
14. Chimenti F, Carradori S, Secci D, Bolasco A, Bizzarri B et al (2010) Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1H)-pyrazole derivatives. Eur J Med Chem 45:800-804
15. Close WJ, Tiffany BD, Spielman MA (1949) The analgesic activity of some benzoxazolone derivatives. J Am Chem Soc 71:1265-1268
16. Dawey W, Tivey DJ (1958) Chalcones and related compounds. Part IV. Addition of hydrogen cyanide to chalcones 242:1230-1236
17. Dong F, Jian C, Zhenghao F, Kai G, Zuliang L (2008) Synthesis of chalcones via Claisen-Schmidt condensation reaction catalyzed by acyclic acidic ionic liquids. Catal Commun 9:1924-1927
18. Drukarch B, van Muiswinkel FL (2000) Drug treatment of Parkinson's disease. Time for phase II. Biochem Pharmacol 59:1023-1031
19. Gökçe M, Geciken AE, YIldIrIm E, Tosun AU (2001) Synthesis and anticonvulsant activity of 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(o/p- substituted benzal)hydrazone derivatives. Arzneimittelforschung 58:537-542
20. Gökhan N, Yeşilada A, Uçar G, Erol K, Bilgin AA (2003) 1-N-Substituted thiocarbamoyl-3-phenyl-5-thienyl-2-pyrazolines: synthesis and evaluation as MAO inhibitors. Arch Pharm Pharm Med Chem 336:362-371
21. Gökhan-Kelekçi N, Yabanoǧlu S, Küpeli E, SalgIn U, Özgen Ö et al (2007) A new therapeutic approach in alzheimer disease: some novel pyrazole derivatives as dual MAO-B inhibitors and antiinflammatory analgesics. Bioorg Med Chem 15:5775-5786
22. Gökhan-Kelekçi N, Koyunoǧlu S, Yabanoǧlu S, Yelekçi K, Özgen Ö et al (2009) New pyrazoline bearing 4(3H)-quinazolinone inhibitors of monoamine oxidase: synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity. Bioorg Med Chem 17:675-689
23. 2 -pyrazolines. Il Farmaco 55:256-263
24. Irie K, Watanabe K (1980) Aldol condensations with metal(II) complex catalysts. Bull Chem Soc Jpn 53:1366-1371
25. Kubota Y, Ikeya H, Sugi Y, Yamada T, Tatsumi T (2006) Organic-inorganic hybrid catalysts based on ordered porous structures for Michael reaction. J Mol Catal A-Chem 249:181-190
26. Lipson VV, Desenko SM, Shirobokova MG, Borodina VV, Musatov VI (2005) Chemical reactions of 2-methyl-5,7-diphenyl-6,7-dihydropyrazolo[1,5-a]pyrimidine (New York, NY, United States). Chem Heterocycl Compd 41:492-495
27. Manna F, Chimenti F, Bolasco A, Secci D, Bizzarri B et al (2002) Inhibition of amine oxidases activity by 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)- pyrazole derivatives. Bioorg Med Chem Lett 12:3629-3633
28. Milcent R, Akhnazarian A, Lensen N (1996) Synthesis of 1-(2-hydroxyphenyl)-2,4-imidazolidinedione derivatives through cyclic transformations of ethyl 2-oxo-3(2H)-benzoxazoleacetate derivatives. J Heterocycl Chem 33:1829-1833
29. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ (2009) Autodock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comp Chem 16:2785-2791
30. Önkol T, Gökçe M, Tosun AU, Polat S, Serin MS, Tezcan S (2008) Microwave synthesis and antimicrobial evaluation of 5-chloro-2(3H)- benzoxazolinone-3-acetyl-2-(p-substituted benzal)hydrazone and 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(p-substituted acetophenone)hydrazone derivatives. Turk J Pharm Sci 5:155-166
31. Özdemir Z, Kandilci HB, Gümüşel B, ÇalIş Ü, Bilgin AA (2007) Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur J Med Chem 42:373-379
32. Özdemir Z, Kandilci HB, Gümüşel B, ÇalIş Ü, Bilgin AA (2008) Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-thienyl)-pyrazoline derivatives. Arch Pharm Chem Life Sci 341:701-707
33. Palaska E, Aytemir M, Uzbay IT, Erol D (2001) Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines. Eur J Med Chem 36:539-543
34. Palaska E, AydIn F, Uçar G, Erol D (2008) Synthesis and monoamine oxidase inhibitory activities of 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-1H- pyrazole derivatives. Arch Pharm Chem Life Sci 341:209-215
35. Potts KT, Bhattacharjee D, Kanemasa S (1980) Mesoionic compounds. 52. Attempted synthesis of the anhydro-2-hydroxyoxazolo[2,3b-]oxazolium hydroxide system. J Org Chem 45:4985-4988
36. Şahin ZS, SalgIn-Gökşen U, Gökhan-Kelekçi N, IşIk Ş (2011) Synthesis, crystal structures and DFT studies of 1-[2-(5-methyl-2-benzoxazolinone-3-yl)acetyl]-3-phenyl-5-(3,4-dimethoxyphenyl) -4,5-dihydro-1H-pyrazole and 1-[2-(5-chloro-2-benzoxazolinone-3-yl)acetyl]-3- phenyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole. J Mol Struct 1006:147-158
37. SalgIn-Gökşen U, Gökhan-Kelekçi N, Göktaş Ö, Köysal Y, KIlIç E et al (2007) 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorg Med Chem 15:5738-5751
38. Sarabhai KP, Mathur KBL (1963) Some arylation reactions with diazotized 3,4,5-trimethoxyaniline. Preparation of 3,4,5-trimethoxychalcone and 3,4,5-trimethoxybenzaldehyde. Indian J Chem 1:482-483
39. Schapira AH (2007) Treatment options in the modern management of Parkinson disease. Arch Neurol 64:1083-1088
40. Secci D, Bolasco A, Chimenti P, Carradori S (2011) The state of the art of pyrazole derivatives as monoamine oxidase inhibitors and antidepressant/ anticonvulsant agents. Curr Med Chem 18:5114-5144
41. Shekarchi M, Pirali-Hamedani M, Navidpour L, Adib N, Shafiee A (2008) Synthesis, antibacterial and antifungal activities of 3-aryl-5-(pyridin-3-yl)-4, 5-dihydropyrazole-1-carbothioamide derivatives. J Iran Chem Soc 5:150-158
42. Son S-Y, Ma J, Kondou Y, Yoshimura M, Yamashita E, Tsukihara T (2008) Structure of human monoamine oxidase A at 2.2-Å resolution: the control of opening the entry for substrates/inhibitors. P Natl Acad Sci USA 105:5739-5744
43. Ueno Y, Yadav LDS, Okawara M (1983) Carbon-carbon bond formation via phosphine-initiated cleavage of oxosulphides. Chem Lett 6:831-834
44. Ünlü S, Erdoǧan H, Sunal R (1992) Synthesis of some (2-benzoxazolinones-3-yl)alkonoic acid derivatives and their analgesic properties. Hacettepe University J Faculty of Pharm 12:23-31
45. Yamada M, Yasuhara H (2004) Clinical pharmacology of MAO inhibitors: safety and future. Neurotoxicology 25:215-221
46. Yáñez M, Fraiz N, Cano E, Orallo F (2006) Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity. Biochem Biophys Res Commun 344:688-695
47. Yelekçi K, Karahan Ö, Toprakci M (2007) Docking of novel reversible monoamine oxidase-B inhibitors: efficient prediction of ligand binding sites and estimation of inhibitors thermodynamic properties. J Neural Transm 114:725-732