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Abstract
In present study, a novel series of substituted imidazo[2,1-b]thiazole pyrazoline derivatives (2a-e) and (3a-e) from the reference compound imidazo[2,1-b]thiazole chalcones (1a-e) in PEG-400 by using hydrazine hydrate and phenyl hydrazine was synthesized. Characterization of newly synthesized compounds was done using IR and 1H NMR. Further, imidazo[2,1-b]thiazole pyrazoline derivatives were subjected to check their in vitro antioxidant activities at a concentration of 0.5 mmol/L in methanol. Compounds 2c, 2d, 3c, 3d and 3e showed comparatively good activity than standard drug diclofenac. The anti-inflammatory activity of compounds 2c, 2d, 2e, 3c, 3d and 3e were comparable with standard drug. Similarly, all these compounds possess good antioxidant activity as compared to ascorbic acid (vitamin C); compared to the value of DPPH and SOD antioxidant activity 44.18 % and 74.07 %, respectively. These synthesized compounds exhibited a good anti-inflammatory and antioxidant activities hence might be useful in future drug designing studies.
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References
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References
N. Das, B. Dash, M. Dhanawat and S.K. Shrivastava, Design, Synthesis, Preliminary Pharmacological Evaluation, and Docking Studies of Pyrazoline Derivatives, Chem. Pap., 66, 67 (2012); https://doi.org/10.2478/s11696-011-0106-2
P. Arora, V. Arora, H.S. Lamba and D. Wadhwa, Importance of Hetero-cyclic Chemistry: A Review, Int. J. Pharm. Sci. Res., 3, 2947 (2012); https://doi.org/10.13040/IJPSR.0975-8232.3(9).2947-54
A. Al-Mulla, A Review: Biological Importance of Heterocyclic Compounds, Der Pharma Chem., 9, 141 (2017).
S.Y. Jadhav, R.B. Bhosale, S.P. Shirame, V.D. Sonawane, M.G. Hublikar, K.D. Sonawane and R.U. Shaikh, Synthesis and Biological Evaluation of Fluro-hydroxyl Substituted Pyrazole Chalcones as Anti-Inflammatory, Antioxidant and Anti Bacterial Agents, Int. J. Pharma Biosci., 4, 390 (2013).
V.D. Sonawane, Design, Synthesis, Characterization and in vitro Anti-oxidant Screening of Novel Chromone Chalcones, Rev Res., 3, 1 (2013).
B.D. Sonawane, G.S. Rashinkar, K.D. Sonawane, M.J. Dhanavade, V.D. Sonawane and S.V. Patil, Aerosil-Supported Ionic-Liquid-Phase (ASILP) Mediated Synthesis of 2-Substituted Benzimidazole Derivatives as AChE Inhibitors, ChemSelect, 3, 5544 (2018); https://doi.org/10.1002/slct.201702969
D.G. Raut, V.D. Kadu, V.D. Sonawane and R.B. Bhosale, Synthesis of Thiazole Scaffolds by Novel Method and their in vitro Anthelmintic Activity against Indian Adult Earthworm, Eur. J. Biomed. Pharm. Sci., 2, 922 (2015).
M.J. Dhanavade, R.B. Bhosale, D.G. Raut, K.D. Sonawane, S.Y. Jadhav V. D. Sonawane and D.B. Jadhav, Synthesis and Potential Antibacterial Activities of 2-Chloro-N-(4-phenylthiazol-2-yl)acetamide Derivatives, Der Pharma Chem., 8, 292 (2016).
V.E. Rani and L.K. Ravindranath, Synthesis, Characterization and Antimicrobial Evaluation of Novel Mannich Bases Containing Pyrazole-5-one Phosphonates, Open Pharm. Sci. J., 3, 49 (2016); https://doi.org/10.2174/1874844901603010049
L.S.S. Reddy, T. Rajkumar, G. Mrudula and Y. Reddy, Synthesis, Charact-erization, Anti-Oxidant and Anti-Inflammatory Activity Evaluation of Chalcones & Pyrazoline Derivatives, Orient. J. Chem., 31, 189 (2015); https://doi.org/10.13005/ojc/31.Special-Issue1.23
S.Y. Jadhav, R.B. Bhosale, S.P. Shirame, S.B. Patil and S.D. Kulkarni, PEG Mediated Synthesis and Biological Evaluation of Asymmetrical Pyrazole Curcumin Analogues as Potential Analgesic, Anti-Inflammatory and Antioxidant Agents, Chem. Biol. Drug Des., 85, 377 (2015); https://doi.org/10.1111/cbdd.12416
S.Y. Jadhav, S.P. Shirame, S.D. Kulkarni, S.P. Patil, S.K. Pasale and R.B. Bhosale, PEG Mediated Synthesis and Pharmacological Evaluation of Some Fluoro Substituted Pyrazoline Derivatives as Antiinflammatory and Analgesic Agents, Bioorg. Med. Chem. Lett., 23, 2575 (2013); https://doi.org/10.1016/j.bmcl.2013.02.105
R.S. Joshi, P.G. Mandhane, S.D. Diwakar, S.K. Dabhade and C.H. Gill, Synthesis, Analgesic and Anti-inflammatory Activities of Some Novel Pyrazolines Derivatives, Bioorg. Med. Chem. Lett., 20, 3721 (2010); https://doi.org/10.1016/j.bmcl.2010.04.082
S.M. Hipparagi and M.D. Bhanushali, Synthesis and Evaluation of Anti-Tubercular Activity of Some Novel 2-Pyrazoline Derivatives, J. Sci. Soc., 40, 80 (2013); https://doi.org/10.4103/0974-5009.115475
S. Shelke, G. Mhaske, S. Gadakh and C. Gill, Green Synthesis and Biological Evaluation of Some Novel Azoles as Antimicrobial Agents, Bioorg. Med. Chem. Lett., 20, 7200 (2010); https://doi.org/10.1016/j.bmcl.2010.10.111
J. Chen, S.K. Spear, J.G. Huddleston and R.D. Rogers, Polyethylene Glycol and Solutions of Polyethylene Glycol as Green Reaction Media, Green Chem., 7, 64 (2005); https://doi.org/10.1039/b413546f
B.H. Havsteen, The Biochemistry and Medical Significance of the Flavo-noids, Pharm. Therap., 96, 67 (2002); https://doi.org/10.1016/S0163-7258(02)00298-X
V. Hillemane, Y. Nayak, and B.S. Jayashree, Evaluation of the Anti-oxidant Activity of Novel Synthetic Chalcones and Flavonols, Int. J. Chem. Eng. Appl., 3, 216 (2012); https://doi.org/10.7763/IJCEA.2012.V3.189
S. Kumar, D. Kumar, N. Singh and B.D. Vasisht, in-vitro Free Radicals Scavenging and Antioxidant Activity of Moringa oleifera Pods, J. Herb. Med. Toxicol., 1, 117 (2007).
L. Manzocco, M. Anese and M.C. Nicoli, Antioxidant Properties of Tea Extracts as Affected by Processing, LWT-Food Sci Technol., 31, 694 (1998); https://doi.org/10.1006/fstl.1998.0491
J. Robak and R.J. Gryglewski, Flavonoids are Scavengers of Superoxide Anions, Biochem. Pharmacol., 37, 837 (1988); https://doi.org/10.1016/0006-2952(88)90169-4
Y. Murti, A. Goswami and P. Mishra, Synthesis and Antioxidant Activity of Some Chalcones and Flavanoids, Int. J. PharmTech. Res., 5, 811 (2013).