Author(s):
Ranjit V. Gadhave, Bhanudas S. Kuchekar
Email(s):
ranjitgadhave@gmail.com
DOI:
10.5958/0974-360X.2020.00986.5 
Address:
Ranjit V. Gadhave1,2*, Bhanudas S. Kuchekar1,2
1Department of Pharmaceutical Chemistry, MAEER’s Maharashtra Institute of Pharmacy, Kothrud, Pune - 411038, Maharashtra, India.
2School of Pharmacy, MIT World Peace University, Kothrud, Pune - 411 038, Maharashtra, India.
*Corresponding Author
Published In:
Volume - 13,
Issue - 12,
Year - 2020
ABSTRACT:
The present work describes biological evaluation of target molecules designed by molecular docking with 4h1j protein using Autodock Vina docker. Designed novel benzothiazole and coumarin based 6-(3, 5-dimethylpyrazol-1-yl) pyridazin-3-one derivatives were synthesized by condensation of substituted 6-(3,5-dimethylpyrazol-1-yl)pyridazin-3(2H)-one with substituted 2-amino benzothiazoles, substituted 2-oxo-2H-chromene-3-carbonyl chloride or 4-(bromomethyl)-2H-chromen-2-one. Synthesized compounds were characterized by spectral analysis and screened for antioxidant activity using 1, 1-diphenyl-2-picrylhyrazyl radical scavenging, Hydrogen peroxide scavenging and ferric reducing antioxidant power method. The compounds 5c and 9b showed more antioxidant potential and other compounds showed moderate to less activity as compared to standard Ascorbic acid and Butylated hydroxyl toluene.
Cite this article:
Ranjit V. Gadhave, Bhanudas S. Kuchekar. Design, Synthesis, Characterization and Antioxidant activity of Novel Benzothiazole and Coumarin based 6-(3, 5-dimethylpyrazol-1-yl) pyridazin-3-one Derivatives. Research J. Pharm. and Tech. 2020; 13(12):5661-5667. doi: 10.5958/0974-360X.2020.00986.5
Cite(Electronic):
Ranjit V. Gadhave, Bhanudas S. Kuchekar. Design, Synthesis, Characterization and Antioxidant activity of Novel Benzothiazole and Coumarin based 6-(3, 5-dimethylpyrazol-1-yl) pyridazin-3-one Derivatives. Research J. Pharm. and Tech. 2020; 13(12):5661-5667. doi: 10.5958/0974-360X.2020.00986.5 Available on: https://rjptonline.org/AbstractView.aspx?PID=2020-13-12-1
REFERENCES:
1. Sharma D, Bansal R. Synthesis of 2-substituted-4-aryl-6-phenylpyridazine-3(2H)-ones as potential anti-inflammatory and analgesic agents with cardioprotective and ulcerogenic sparing effects. Med Chem Res. 2016; 25: 1574-1589.
2. Mogilski Set al. Antinociceptive, anti-inflammatory and smooth muscle relaxant activities of the pyrrolo[3,4-d]pyridazinone derivatives: Possible mechanisms of action. Pharmacol Biochem Behav. 2015; 133: 99-100.
3. Rathish IGet al. Synthesis and evaluation of anticancer activity of some novel 6-aryl-2-(p-sulfamoylphenyl)-pyridazin-3(2H)-ones. Eur J Med Chem. 2012; 49: 304-309.
4. Xing Wet al. Discovery of novel 2, 6-disubstituted pyridazinone derivatives as acetylcholinesterase inhibitors. Eur J Med Chem. 2013; 63: 95-103.
5. Wang Zet al. Design, synthesis and antiviral activity of novel pyridazines. Eur J Med Chem. 2012; 54: 33-41.
6. SanghPartapet al. Pyridazinone hybrids: Design, synthesis and evaluation as potential anticonvulsant agents. Bioorg Chem. 2018; 77: 74-83.
7. Nayak PSet al. Design, synthesis, molecular docking and biological evaluation of imides, pyridazines and imidazoles derived from itaconic anhydride for potential antioxidant and antimicrobial activities. Jtaibah Uni Sci. 2016; 10(6): 823-838.
8. Bandgar BP et al. Synthesis and biological evaluation of a novel series of pyrazolechalcones as anti-inflammatory, antioxidant and antimicrobial agents. Bioorg Med Chem. 2009; 17(24): 8168-8173.
9. Azma RB et al. Synthesis and Anti-inflammatory Activity of Some New 2-Pyrazoline Derivatives. Research J. Pharm. and Tech. 2010; 3(2): 625-626.
10. Bhat IK et al. Pyrazolines as Potent Antioxidant Agents. Research J. Pharm. and Tech. 2018; 11(5):1978-1980.
11. Yi WU et al. Synthesis of 1, 3-diaryl pyrazole derivatives and evaluation of anticonvulsant and antimicrobial activities. Lat Am J Pharm. 2018; 37(5): 1017-1027.
12. Mosaad SM et al. Synthesis and biological screening of novel pyrazoles and their precursors as potential antiviral agents. Pharmacophore. 2018; 9(1): 126-139.
13. Charles EMet al. Novel Amino-pyrazole ureas with potent in vitro and in vivo Antileishmanial Activity. J Med Chem. 2015; 58: 9615-9624.
14. Mohamed SAet al. Synthesis, structural, characterization and anticancer evaluation of pyrazole derivatives. Med Chem Res. 2018; 27(1): 72-79.
15. Zhao WGet al. Synthesis of pyrazolyl heterocycles and their fungicidal activities. Chin J Chem. 2011; 22: 939-942.
16. K Ravi Kumar et al. Synthesis, characterization and biological evaluation of benzothiazole derivatives as potential antimicrobial and analgesic agents. Asian J. Res. Pharm. Sci. 2017; 7(2):115-119.
17. Tashfeen Aet al. In vitro antitumor and antiviral activities of new benzothiazole and 1, 3, 4-oxadiazole-2-thione derivatives. Acta Pharma. 2008; 58: 135-149.
18. El-Sharkawy KA et al. Design and synthesis of thiazol derivatives with biological evaluations as antitumor agents. Research J. Pharm. and Tech. 2015; 8(5): 520-528.
19. Helena Bet al. Anti-candida activity of four antifungal benzothiazoles, FEMS Micobiol Lett. 1993; 112(3): 329-333.
20. Bele D S, SinghviI. Synthesis and Analgesic Activity of Some Mannich Bases of 6-Substituted-2-Aminobenzothiazole. Research J. Pharm. and Tech. 2008; 1(1):Page 22-24.
21. S. Sangeetha, T. F. Abbs Fen Reji. Antioxidant activities of Methyl and Chlorine substituted 2-(2-alkyl/arylaminothiazol-5-oyl)-N-methylbenzimidazoles. Asian J. Research Chem. 2018; 11(6):835-842.
22. Ratchanok Pingaew et al. Synthesis, biological evaluation and molecular docking of novel chalcone-coumarin hybrids as anticancer and antimalarial agents. Eur J Med Chem. 2014; 85: 65-76.
23. Enas B, Ahmed EM. QSAR study of coumarin derivatives as monoamine oxidase A and B inhibitors. Int J Pharm Res Health Sci. 2018; 6(1): 2324-2327.
24. Jaya RK et al. Synthesis and pharmacological evaluation of Schiff bases of 7-amino-4-methyl coumarins as novel anti-inflammatory agents. Asian J Pharm Pharmacol., 2019; 5(4): 693-700.
25. Al-Majedy Y et al. Antioxidant activity of coumarine compounds. Al-Nahrain J Sci. 2019; 22(1): 1-8.
26. Hao Let al. Novel coumarin-pyrazole caroxamide derivatives as potential topoisomerase 2 inhibitors: Design, synthesis and antibacterial activity. Eur J Med Chem. 2018; 157: 81-87.
27. Manojkumar Pet al. Antioxidant and antibacterial studies of arylazopyrazoles and arylhydrazonopyrazolones containing coumarin moiety. Eur J Med Chem. 2009; 44(11): 4690-4694.
28. Mohammed Aet al. Synthesis and evaluation of some new 1, 3, 4-oxadiazoles bearing thiophene, thiazole, coumarin, pyridine and pyridazine derivatives as antiviral agents. Acta Pharm. 2019; 69: 261-276.
29. Mohareb RM, Gamaan MS. The uses of ethyl 2-(1H-benzo (d) imidazole-2-yl) acetate to synthesis pyrazole, thiophene, pyridine and coumarin derivatives with antitumour activities. Bull Chem Soc Ethiop. 2018; 32(3): 541-557.
30. Zhao B et al. Natural antioxidants protect neurons in Alzheimer’s disease and Parkinson’s disease. Neurochem Res. 2009; 34(4): 630-638.
31. Aruoma OI et al. Free Radicals, Oxidative Stress, and Antioxidants in Human Health and Disease. J Am Oil Chem Soc. 1998; 75(2): 199-212.
32. Bhat KIet al. Synthesis and Antioxidant Activity of Some New Coumarin Incorporated 4-Thiazolidinone Derivatives. Res J Pharm Technol. 2018;11(12): 813-821.
33. Venkatachalam Het al. Synthesis, Characterization and Antioxidant Activities of synthetic chalcones and Flavones. APCBEE Proc. 2012; 3: 209-213.
34. Stefania FB et al. Synthesis and antioxidant activity evaluation of new compounds from hydrazine carbothioamide and 1, 2, 4-triazole class containing diarylsulfone and 2, 4-diflurophenyl moieties. Int J Mol Sci. 2014; 15(6): 10908-10925.
35. Joshi U et al. Evaluation of Antioxidant Activity of Aqueous Extract Bark of Ficusglomerata. Research J. Pharm. and Tech. 2008; 1(4): 537-538.
36. Sathe PS et al. Synthesis, Characterization and Investigation of Anti-Oxidant Activity of Hydrazide–hydrazone Derivatives of 2-(2-Isopropyl-5-methyl phenoxy) Acetohydrazide. Asian J. Research Chem. 2018; 11(3):533-538.
37. Munir O et al. Determination of In-vitro activity of funnel (Foeniculum vulgare) seed extracts. LWT-Food Sci Technol. 2003; 36(2): 263-271.
38. Gulcin AI et al. Determination of antioxidant activity of lichen Centriaislandica. , J Ethnopharmacol. 2002; 79(3): 325-329.
39. Thomas R et al. In silico Docking Approach of Coumarin Derivatives as an Aromatase Antagonist. Research J. Pharm. and Tech. 2015; 8(12): 1673-1678.
40. Zadorozhnii PV et al. Molecular Docking Studies of N-(((5-Aryl-1, 3, 4-oxadiazol-2-yl)amino)methyl)- and N-(2, 2, 2-Trichloro-1-((5-aryl-1, 3, 4-oxadiazol-2-yl)amino)ethyl)carboxamides as Potential Inhibitors of GSK-3β. Research J. Pharm. and Tech. 2019; 12(2):523-530.