Design, synthesis and evaluation of antidepressant activity of novel 2-methoxy 1, 8 naphthyridine 3-carboxamides as 5-HT3 receptor antagonists

Chemical Biology and Drug Design

Volumn 83, Issue 5, 2014, Pages 583-591

  Mahesh, Radhakrishnan ^a   Dhar, Arghya Kusum ^a   Jindal, Ankur ^a   Bhatt, Shvetank ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

1,8 naphthyridine 3 carboxamides; antidepressant; forced swim test; spontaneous locomotor activity

Indexed keywords

(2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL) (4 BUTYL PIPERAZINE 1 YL) METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL) (4 ETHYL PIPERAZINE 1 YL) METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL) (4 METHYL PIPERAZINE 1YL) METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL) (4 PROPYL PIPERAZINE 1YL) METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL)[4 (2 CHLOROPHENYL) PIPERAZINE 1 YL] METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL)[4 (2 METHOXY PHENYL) PIPERAZINE 1 YL] METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL)[4 (2 METHYL PHENYL) PIPERAZINE 1 YL] METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL)[4 (3 CHLOROPHENYL) PIPERAZINE 1 YL] METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL)[4 (3 METHOXY PHENYL) PIPERAZINE 1 YL] METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL)[4 (4 CHLOROPHENYL) PIPERAZINE 1 YL] METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL)[4 (4 METHOXY PHENYL) PIPERAZINE 1 YL] METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL)[4 (4 METHYL PHENYL) PIPERAZINE 1 YL] METHANONE; (2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL)[4 (4 NITROPHENYL) PIPERAZINE 1 YL]METHANONE; 2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL (4 BENZYLPIPERAZINE 1 YL) METHANONE; 2 METHOXY 1, 8 NAPHTHYRIDIN 3 YL (4 PHENYLPIPERAZINE 1 YL) METHANONE; 2 METHOXY 1, 8 NAPHTHYRIDINE 3 CARBOXAMIDE; ANTIDEPRESSANT AGENT; ONDANSETRON; SEROTONIN 3 ANTAGONIST; UNCLASSIFIED DRUG; AMIDE; NAPHTHYRIDINE DERIVATIVE; SEROTONIN 3 RECEPTOR;

ANIMAL EXPERIMENT; ANTIDEPRESSANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; FALSE NEGATIVE RESULT; FALSE POSITIVE RESULT; FORCED SWIM TEST; LOCOMOTION; MOUSE; MYENTERIC PLEXUS; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY; ANIMAL; ANIMAL BEHAVIOR; CHEMISTRY; DRUG EFFECTS; GUINEA PIG; METABOLISM; MOTOR ACTIVITY; SYNTHESIS;

CAVIA; MUS;

AMIDES; ANIMALS; ANTIDEPRESSIVE AGENTS; BEHAVIOR, ANIMAL; DRUG DESIGN; GUINEA PIGS; MICE; MOTOR ACTIVITY; MYENTERIC PLEXUS; NAPHTHYRIDINES; RECEPTORS, SEROTONIN, 5-HT3; SEROTONIN 5-HT3 RECEPTOR ANTAGONISTS;

EID: 84899480090     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12271     Document Type: Article

References (34)

1. Belmaker R.H., Agam G.N., (2008) Major depressive disorder. Engl J Med; 358: 55-68.
2. Rosenzweig-Lipson S., Beyer C.E., Hughes Z.A., Khawaja X., Rajarao S.J., Malberg J.E., Rahman Z., Ring R.H., Schechter L.E., (2007) Differentiating antidepressants of the future: efficacy and safety. Pharmacol Ther; 113: 134-153. (Pubitemid 46017069)
3. Cryan J.F., Markou A., Lucki I., (2002) Assessing antidepressant activity in rodents: recent developments and future needs. Trends Pharmacol Sci; 23: 238-245. (Pubitemid 34465544)
4. Montgomery S.A., Kennedy S.H., Burrows G.D., Lejoyeux M., Hindmarch I., (2004) Absence of discontinuation symptoms with agomelatine and occurrence of discontinuation symptoms with paroxetine: a randomized, double-blind, placebo-controlled discontinuation study. Int Clin Psychopharmacol; 19: 271-280. (Pubitemid 39141943)
5. Pinder R.M., Wieringa J.H., (1993) Third-generation antidepressants. Med Res Rev; 13: 259-325. (Pubitemid 23114517)
6. Pinder R.M., (1990) The toxicity of antidepressants in overdose: incidence and mechanisms. Int Rev Psychiatry; 2: 213-227.
7. Barnes N.M., Sharp T., (1999) A review of central 5-HT receptors and their function. Neuropharmacology; 38: 1083-1152. (Pubitemid 29292403)
8. Wolf H., (2000) Preclinical and clinical pharmacology of the 5-HT3 receptor antagonists. Scand J Rheumatol; 29 (Suppl. 113): 37-45. (Pubitemid 32016435)
9. Hsu E.S., (2010) A review of granisetron, 5-hydroxytryptamine3 receptor antagonists, and other antiemetics. Am J Ther; 17: 476-486.
10. 3) antagonists. Curr Med Chem; 1: 171-199.
11. Srivastava S.K., (1998) Antidepressant activity of ondansetron, a 5-HT3 antagonist. Indian J Pharmacol; 30: 411-412. (Pubitemid 29030257)
12. 3 receptor antagonists reverse helpless behaviour in rats. Eur J Pharmacol; 212: 73-78.
13. Costall B., Naylor R.J., (1992) Anxiolytic potential of 5-HT3 receptor antagonists. Pharmacol Toxicol; 70: 157-162.
14. Zhang Z.J., Schmidt D.E., de Paulis T., Trivedi B.L., Onaivi E.S., Ebert M.H., Hewlett W.A., (2001) Anxiolytic-like effects of DAIZAC, a selective high-affinity 5-HT(3) receptor antagonist, in the mouse elevated plus-maze. Pharmacol Biochem Behav; 69: 571-578. (Pubitemid 32758743)
15. Devadoss T., Pandey D.K., Mahesh R., Yadav S., (2010) Effect of acute and chronic treatment with QCF-3 (4-benzylpiperazin-1-yl) (quinoxalin-2-yl) methanone, a novel 5-HT(3) receptor antagonist, in animal models of depression. Pharmacol Rep; 62: 245-257.
16. Mahesh R., Rajkumar R., Minasri B., Perumal R.V., (2007) Potential antidepressants: pharmacology of 2-(4-methyl piperazin-1-yl)-1,8-naphthyridine- 3-carbonitrile in rodent behavioural models. Pharmazie; 62: 919-924. (Pubitemid 350305768)
17. Rajkumar R., Mahesh R., Minasri B., (2008) Antidepressant-like effects of serotonin type-3 antagonist, ondansetron: an investigation in behaviour-based rodent models. Behav Pharmacol; 19: 29-40.
18. 3 receptor in depression: a probable neuronal target? J Psychopharmacol; 24: 455-469.
19. Hibert M.F., Hoffmann R., Miller R.C., Carr A.A., (1990) Conformation-activity relationship study of 5-HT3 receptor antagonists and a definition of a model for this receptor site. J Med Chem; 33: 1594-1600. (Pubitemid 20180616)
20. 3 receptor ligands. J Med Chem; 55: 8603-8614.
21. Mahesh R., Devadoss T., Dhar A.K., Venkatesh S.M., Mundra S., Pandey D.K., Bhatt S., Jindal A.K., (2012) Ligand-based design, synthesis, and pharmacological evaluation of 3-Methoxyquinoxalin-2-carboxamides as structurally novel serotonin type-3 receptor antagonists. Arch Pharm (Weinheim); 345: 687-694.
22. Mahesh R., Devadoss T., Pandey D.K., Yadav S.K., (2011) Quinoxalin-2-carboxamides: synthesis and pharmacological evaluation as serotonin type-3 (5-HT3) receptor antagonists. J Enzyme Inhib Med Chem; 26: 610-615.
23. Mahesh R., Devadoss T., Pandey D.K., Bhatt S., Yadav S.K., (2010) Design, synthesis and structure-activity relationship of novel quinoxalin-2- carboxamides as 5-HT3 receptor antagonists for the management of depression. Bioorg Med Chem Lett; 20: 6773-6776.
24. Mahesh R., Devadoss T., Pandey D.K., Bhatt S., (2011) Discovery of new anti-depressants from structurally novel 5-HT3 receptor antagonists: design, synthesis and pharmacological evaluation of 3-ethoxyquinoxalin-2-carboxamides. Bioorg Med Chem Lett; 21: 1253-1256.
25. Majewicz T.G., Caluwe P., (1974) Facile synthesis of 2- aminonicotinaldehyde. J Org Chem; 39: 720-722.
26. Xiao Y., Chen X., Karra S.R., Huck B.R., Sutton A.E., Goutopoulos A., (2010) Naphthyridininones as aurora kinase inhibitors Patent, WO 2010/002779 A2.
27. Paton W.D.M., Zar A.M., (1968) The origin of acetylcholine released from guinea-pig intestine and longitudinal muscle strips. J Physiol; 194: 13-33.
28. Perumal R.V., Mahesh R., (2006) Synthesis and biological evaluation of a novel structural type of serotonin 5-HT3 receptor antagonists. Bioorg Med Chem Lett; 16: 2769-2772.
29. Mahesh R., Perumal R.V., Pandi P.V., (2004) Pharmacophore based synthesis of 3-chloroquinoxaline-2-carboxamides as serotonin3 (5-HT3) receptor antagonist. Biol Pharm Bull; 2: 1403-1405. (Pubitemid 41701683)
30. 2 and affinity constants for pharmacological competitive antagonists be estimated? J Pharm Pharmacol; 30: 312-313.
31. Boissier J.R., Simon P., (1965) Action of caffeine on the spontaneous motility of the mouse. Arch Int Pharmacodyn Ther; 158: 212-221.
32. Porsolt R.D., Le Pichon M., Jalfre M., (1977) Depression: a new animal model sensitive to antidepressant treatments. Nature; 266: 730-732. (Pubitemid 8073804)
33. Porsolt R.D., Bertin A., Jalfre M., (1977) Behavioral despair in mice: a primary screening test for antidepressants. Arch Int Pharmacodyn Ther; 229: 327-336. (Pubitemid 8225714)
34. Mahesh R., Jindal A., Gautam B., Bhatt S., Pandey D., (2011) Evaluation of anti-depressant-like activity of linezolid, an oxazolidinone class derivative-an investigation using behavioral tests battery of depression. Biochem Biophys Res Commun; 409: 723-726.