Research Articles

Synthesis and Antidepressant activity of pyrazoline based MAO-inhibitors

Vol. 3 No. 1 (2016) 1-3 Published January 15, 2016

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Abstract

A series of nine 3-(2-hydroxyphenyl)-5-aryl-N-phenyl-4,5-dihydropyrazole-1-carbothioamide derivative s (3a-3i) that were earlier reported as potent rMAO-A inhibitors were evaluated for their antidepressant activity in Porsolt's behavioral despair test (forced swim test) and Tail Suspension test activity, among them, compounds (3e and 3h) were found to have potent antidepressant activity. Reduction in duration of immobility was significant for all the compounds in Porsolts swim test compared with tail suspension test. 3h was further evaluated for anxiolytic activity in Elevated plus maze and was found to be devoid of it.

References

  1. Levai, A. Synthesis of Heterocyclic Compounds by the Reactions of Exocyclic ?, ??unsaturated Ketones. J Heterocycl Chem 2004, 41 (3), 299-310. http://dx.doi.org/10.1002/jhet.5570410301 DOI: https://doi.org/10.1002/jhet.5570410301
  2. Lavai, A. Synthesis of 2?pyrazolines by the Reactions of ?, ??unsaturated Aldehydes, Ketones, and Esters with Diazoalkanes, Nitrile Imines, and Hydrazines. J Heterocycl Chem 2002, 39 (1), 1-13. http://dx.doi.org/10.1002/jhet.5570390101 DOI: https://doi.org/10.1002/jhet.5570390101
  3. Lvai, A. Synthesis of Pyrazolines by the Reactions Of?, ?-Enones with Diazomethane and Hydrazines (review). Chem Heterocycl Compd 1997, 33 (6), 647-659. http://dx.doi.org/10.1007/BF02291794 DOI: https://doi.org/10.1007/BF02291794
  4. Rahman, M. A.; Siddiqui, A. A. Pyrazoline Derivatives: A Worthy Insight into the Recent Advances and Potential Pharmacological Activities. Int J Pharm Sci Drug Res 2010, 2 (3), 165-175. DOI: https://doi.org/10.4172/2150-3494.1000021
  5. Kumar, S.; Bawa, S.; Drabu, S.; Kumar, R.; Gupta, H. Biological Activities of Pyrazoline Derivatives-A Recent Development. Recent Pat Antiinfect Drug Discov 2009, 4 (3), 154-163. http://dx.doi.org/10.2174/157489109789318569 DOI: https://doi.org/10.2174/157489109789318569
  6. Secci, D.; Carradori, S.; Bolasco, A.; Bizzarri, B.; DAscenzio, M.; Maccioni, E. Discovery and Optimization of Pyrazoline Derivatives as Promising Monoamine Oxidase Inhibitors. Curr Top Med Chem 2012, 12 (20), 2240-2257. http://dx.doi.org/10.2174/156802612805220057 DOI: https://doi.org/10.2174/156802612805220057
  7. Secci, D.; Bolasco, A.; Chimenti, P.; Carradori, S. The State of the Art of Pyrazole Derivatives as Monoamine Oxidase Inhibitors and Antidepressant/anticonvulsant Agents. Curr Med Chem 2011, 18 (33), 5114-5144. http://dx.doi.org/10.2174/092986711797636090 DOI: https://doi.org/10.2174/092986711797636090
  8. Zeller, E. A.; Barsky, J. In Vivo Inhibition of Liver and Brain Monoamine Oxidase by 1-Isonicotinyl-2-Isopropyl Hydrazine. Exp Biol Med 1952, 81 (2), 459-461. http://dx.doi.org/10.3181/00379727-81-19910 DOI: https://doi.org/10.3181/00379727-81-19910
  9. Yanez, M.; Padin, J. F.; Arranz-Tagarro, J. a; Camina, M.; Laguna, R. History and Therapeutic Use of MAO-A Inhibitors: A Historical Perspective of Mao-a Inhibitors as Antidepressant Drug. Curr Top Med Chem 2012, 12, 2275-2282. http://dx.doi.org/10.2174/156802612805220011 DOI: https://doi.org/10.2174/156802612805220011
  10. BLACKWELL, B.; MARLEY, E.; PRICE, J.; TAYLOR, D. Hypertensive Interactions Between Monoamine Oxidase Inhibitors and Foodstuffs. Br J Psychiatry 1967, 113 (497), 349-365. http://dx.doi.org/10.1192/bjp.113.497.349 DOI: https://doi.org/10.1192/bjp.113.497.349
  11. Blackwell, B. Hypertensive Crisis due to Monoamine-Oxidase Inhibitors. Lancet 1963, 282 (7313), 849-851. http://dx.doi.org/10.1016/S0140-6736(63)92743-0 DOI: https://doi.org/10.1016/S0140-6736(63)92743-0
  12. Ramachandraih, C. T.; Subramanyam, N.; Bar, K. J.; Baker, G.; Yeragani, V. K. Antidepressants: From MAOIs to SSRIs and More. Indian J Psychiatry 2011, 53 (2), 180. http://dx.doi.org/10.4103/0019-5545.82567 DOI: https://doi.org/10.4103/0019-5545.82567
  13. Youdim, M. B.; Edmondson, D.; Tipton, K. F. The Therapeutic Potential of Monoamine Oxidase Inhibitors. Nat Rev Neurosci 2006, 7 (4), 295-309. http://dx.doi.org/10.1038/nrn1883 DOI: https://doi.org/10.1038/nrn1883
  14. Jayaprakash, V.; Sinha, B. N.; Ucar, G.; Ercan, A. Bioorganic & Medicinal Chemistry Letters Pyrazoline-Based Mycobactin Analogues as MAO-Inhibitors. Bioorg Med Chem Lett 2008, 18 (24), 6362-6368. http://dx.doi.org/10.1016/j.bmcl.2008.10.084 DOI: https://doi.org/10.1016/j.bmcl.2008.10.084
  15. Porsolt, R. D.; Anton, G.; Blavet, N.; Jalfre, M. Behavioural Despair in Rats: A New Model Sensitive to Antidepressant Treatments. Eur J Pharmacol 1978, 47, 379-391. http://dx.doi.org/10.1016/0014-2999(78)90118-8 DOI: https://doi.org/10.1016/0014-2999(78)90118-8
  16. Steru, L.; Chermat, R.; Thierry, B.; Simon, P. The Tail Suspension Test: A New Method for Screening Antidepressants in Mice. Psychopharmacology (Berl). 1985, 85, 367-370. http://dx.doi.org/10.1007/BF00428203 DOI: https://doi.org/10.1007/BF00428203
  17. Pellow, S.; File, S. E. Anxiolytic and Anxiogenic Drug Effects on Exploratory Activity in an Elevated plus-Maze: A Novel Test of Anxiety in the Rat. Pharmacol Biochem Behav 1986, 24 (3), 525-529. http://dx.doi.org/10.1016/0091-3057(86)90552-6 DOI: https://doi.org/10.1016/0091-3057(86)90552-6

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Badavath, V. N.; Kumar, A.; Jadav, S. S.; Pattnaik, A. K.; Jayaprakash, V.; Sinha, B. N. Synthesis and Antidepressant Activity of Pyrazoline Based MAO-Inhibitors. J Pharm Chem 2016, 3 (1), 1-3. https://doi.org/10.14805/jphchem.2016.art45.
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Received
August 7, 2015
Published
January 15, 2016
Section
Research Articles
Pages
1-3

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