Development of selective and reversible pyrazoline based MAO-B inhibitors: Virtual screening, synthesis and biological evaluation

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 7, 2011, Pages 1969-1973

  Mishra, Nibha ^a   Sasmal, D ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Monoamine oxidase; Pyrazoline; Virtual screening

Indexed keywords

3 ANTHRACENE 5 ARYL 4,5 DIHYDRO 1H PYRAZOLE; 3,5 DIARYL PYRAZOLINE DERIVATIVE; ALDEHYDE; ANTHRACENE 9 CARBOXALDEHYDE; CHALCONE DERIVATIVE; MONOAMINE OXIDASE B INHIBITOR; PYRAZOLE DERIVATIVE; PYRAZOLINE DERIVATIVE; PYRIDINE 2 YL; SELEGILINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HYDROPHOBICITY; MOLECULAR DOCKING; NONHUMAN; PHYSICAL CHEMISTRY; PROTON TRANSPORT; SPECTROPHOTOMETRY;

ANIMALS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG EVALUATION, PRECLINICAL; HUMANS; MODELS, MOLECULAR; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PYRAZOLES; RATS;

RATTUS;

EID: 79952484009     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.02.030     Document Type: Article

References (13)

1. Shih, J. C.; Chen, K.; Ridd, M. J. Annu. Rev. Neurosci. 1999, 22, 197.
2. Riederer, P.; Lachenmayer, L.; Laux, G. Curr. Med. Chem. 2004, 11, 2033.
3. Strolin Benedetti, M.; Dostert, P. Adv. Drug Res. 1992, 23, 65.
4. Karuppasamy, M.; Mahapatra, M.; Yabanoglu, S.; Ucar, G.; Sinha, B. N.; Basu, A.; Mishra, N.; Sharon, A.; Kulandaivelu, U.; Jayaprakash, V. Bioorg. Med. Chem. 2010, 18, 1875.
5. Sahoo, A.; Yabanoglu, S.; Sinha, B. N.; Ucar, G.; Basu, A.; Jayaprakash, V. Bioorg. Med. Chem. Lett. 2010, 20, 132.
6. Stirrett, K. L.; Ferreras, J. A.; Jayaprakash, V.; Sinha, B. N.; Ren, T.; Quadri, L. E. Bioorg. Med. Chem. Lett. 2008, 18, 2662.
7. Schüller, A.; Schneider, G.; Byvatov, E. QSAR Comb. Sci. 2003, 22, 719.
8. Docking methods.
9. Sharma, V.; Pattanaik, K. K.; Jayprakash, V.; Basu, A.; Mishra, N. Bioinformation 2009, 4, 84.
10. De Colibus, L.; Li, M.; Binda, C.; Lustig, A.; Edmondson, D. E.; Mattevi, A. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12684.
11. Son, S. Y.; Ma, J.; Kondou, Y.; Yoshimura, M.; Yamashita, E.; Tsukihara, T. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 5739.
12. General procedure for the synthesis of chalcones (1-10). To a solution of different acetophenone (0.01 M) and anthracene-9-carboxaldehyde (0.01 M) in ethanol (10 ml) was added aqueous solution of Sodium hydroxide (60%) drop wise with continuous stirring at 0 °C over a period of 2 h. The reaction mixture was kept at room temperature for about 48 h with occasional shaking. After 48 h it was poured into ice-cold water. In case hydroxy chalcone pH was adjusted to 2 using 6 N hydrochloric acid. The yellow precipitate obtained was filtered, washed, dried and recrystallized from dry methanol. The intermediates 1-10 were obtained. General procedure for the synthesis of 3-anthracene-5-aryl-4, 5-dihhydro-1Hpyrazole (11-20). Appropriate chalcone (1-2) was treated with 10 times excess of hydrazine hydrate (80%) in dry ethanol and refluxed for 3-6 h. The hot reaction mixture was then poured into ice-cold water. The solid separated out was filtered, washed, dried and recrystallized from ethanol to afford respective pyrazoline (3-4).
13. Holt, A.; Sharman, D. F.; Baker, G. B.; Palcic, M. M. Anal. Biochem. 1997, 244, 384.