Synthesis, characterization & biological evaluation of 1, 3, 4- oxadiazoles as antioxidant agents
DOI:
https://doi.org/10.56511/JIPBS.2016.v3.i03.pp104-113Abstract
A novel series of 1,3,4-oxadiazole, 5-[4-4′-chlorophenyl)-1,3-thiazole-2yl]-1,3,4-oxadiazole-2-thione (5) were synthesized as per literature method. It was further derivatized in to mannich bases 5-[4-4′-chloro thiazole-2yl]-3-substituted-1,3,4-oxadiazole-2-thione [5a-e]. Physical characterization of compounds which were done by identifying melting point, Rf value, percentage yield and solubility. The structures of these compounds were then identified using UV, FT-IR, 1HNMR and MASS spectral analysis. The derivatives were then screened for antioxidant activity. The antioxidant characters of the synthesized compounds were found out by DPPH, Nitric oxide and Hydrogen peroxide scavenging assays. Compound ‘5c’ showed maximum radical scavenging potential in all the three methods, due to presence of electron donating substituents like diethyl group.
Keywords:
1,3,4-oxadiazole, Mannich bases, Antioxidant activity, DPPH assay, H2O2 Scavenging assayDownloads
References
Asif Hussain, Mohammed Ajmal: Synthesis of novel 1,3,4-oxadiazoles derivatives and their biological properties. Acta Pharmaceutica 2009; 59: 223-233.
Adan A. Kadi, Naner R. EL – Brollosy, Omar A. Al Deeb Elsayed E. Habib, Tarek M. Ibrahim, Ali A. El mam: Synthesis, Table 4. Hydrogen peroxide radical scavenging assay results: % Scavenging Activity At Different Concentrations IC 50 60 μg/ml 80 μg/ml 100 μg/ml 55.19±0.226 65.93±0.662 67.14±0.653 47.1 58.83±0.152 60.48±0.353 62.50±0.452 49.1 58.82±0.623 62.12±0.621 63.63±0.236 43.3 56.52±0.532 59.89±0.623 61.39±0.425 45.6 55.57±0.173 56.61±0.535 58.63±0.654 50.6 71.47±0.36 89.22±0.621 96.19±0.456 26.9 values in μg/ml for samples were determined using ED50 plus of the mean(SEM) antimicrobial and anti-inflammatory activities of novel 2-( 1adamantyl) – 5 substituted – 1,3,4 – oxadiazoles and 2- (1adamantylamino) – 5substituted – 1,3,4 – thiadiazoles. European Journal of Medicinal Chemistry 2007; 42(2):235242.
Kumar G.V.S, Rajendra Prasad Y, Mallikarjuna B.P Chandrashekar S.M, Kistayya L: Synthesis of some novel 2substituted-5-[isopropylthiazole] clubbed 1,2,4-triazoleand 1,3,4-oxadiazole as potential antimicrobial and antitubercular agents. European Journal of Medicinal Chemistry 2010; 45:2063-2074
Girish R. Bankar, Gopalankutty Nampurath, Praveen G. Nayak, Shoumyo Bhattacharya: A possible correlation between the correction of endothelial dysfunction and normalization of high blood pressure by 1,3,4-oxadiazole derivatives. Chemico-biological interactions 2010; 183(227):327-331.
Prakash O, Kumar M, Sharma C, Aneja K.R: Hypervalent iodine (iii) mediated synthesis of novel unsymmetrical 2,5disubstituted 1,3,4-oxadiazole as antibacterial and antifungal agents. European Journal of Medicinal Chemistry 2010; 45(97):4252-4257.
Milda Malvina Busbuliena, Virginija Jakuskiene, Giedrate Mekuskiena, Emilija Udrenaite, Romualdas Smicius, Povilas Vainilavicius: Synthesis and antiinflammatory activity of derivatives of 5- [(2disubsituted amino-6methylpyrimidine)-sulfanylmethyl]-3H1,3,4oxadiazole-2-thiones. IL farmaco 2004; 45:767-774.
YarShahar mohammed, Akthar Wasim Mohammed: Synthesis and anticonvulsant activity of substituted oxadiazole and thiadiazole derivatives. ActaPharmaceutica 2007; 66(4):393-397.
Padmavathi V, Reddy G.S, Padmaja A, Kodaiah P, Ali Shazia: Synthesis, antimicrobial and cytotoxic activities of 1,3,4 – oxadiazoles, 1,3,4 – thiadiazoles and 1,2,4 triazole. European Journal of Medicinal Chemistry 2009; 44:21062112.
Harish Kumar, Sadique A. JavedSuroor A Khan, Mohammed Amir: 1,3,4 – oxadiazoles, thiadiazoles and 1,2,4 triazole derivatives of biphenyl -4-yloxy acetic acid synthesis and preliminary evaluation of biological properties. European Journal of Medicinal Chemistry 2008; 43(12):2688-2698.
Akthar M Hussain A, Ajmal M: Araylpropionic acid based 2,5disubstituted-1,3,4 – oxadiazoles: synthesis and their anti inflammatory and analgesic activities. European Journal of Medicinal Chemistry 2009; 44 :23722378.
Idrees G.A, Aly O.M, AbnoRahma,Gel-D, Radwan M.F: Design synthesis and hypolipidemic activity of novel 2- (naphthalene-2-yloxy) propionic acid derivatives as desmethyl fibrate analogs . European Journal of Medicinal Chemistry 2009; 44 :3973-3980.
Kumar D Sundaree S, Johnson E.O, Shah K: An efficient synthesis and biological study of novel indolyl1,3,4oxadiazoles as potent anticancer agents. Bioorganics and Medicinal Chemistry Letter 2009; 19:4492-4494.
Raieed M Shakir, Azhar Ariffin, Mohmood Ameen Abdulla: Synthesis of 2,5-Disubstituted 1,3,4-oxadiazoles bearing 2,6Di-test Butylphenol moieties and Evaluation of their Antioxidant activity molecules Molecules 2014; 19:3436-3449.
Sashikant V. Bhandari, Kailash G Bothara, Mayunesh K Rant, Ajit A patil, Aniket P Sarkate, Vinod J Mokale: Design, Synthesis and Evaluation of Anti Inflammatory, Analgesic and ulcerogenicity studies of novel 5-substituted phenacyl-1,3,4oxadiazole-2-thiol and Schiff bones of Diclofenac acid as nonulcerogenic Derivatives. Bioorganics and Medicinal Chemistry Letter 2008; 16:1822-1831.
Somani R. R, Shirodhkar P.Y: Oxadiazole: a biologically active heterocycles. Der Pharm Chemica 2009; 1(1):130-140.
Lingappa Mallesha, kikkeri P Harish, Kikkeri NMohanan, Nanjappagowda D Rekha: Invitro antioxidant activity of 1-[54-methoxy-phenyl)-1,3,4 oxadiazole-2-yl]- piperazine derivatives. Canadian chemical transactions 2014; 2(4):518-525.
Kikkeri N Mohana, Chikkur B Pradeep kumar: Synthesis and antioxidant activity of 2-Amino-5-methyl thiazole derivative containing 1,3,4-oxadiazole -2-thiol moiety. ISRN organic chemistry 2013; 1-4.
N. Chidananda, Bojapoojary, V Sumangala, Prajwal I lobo: Condensed bridge heat nitrogen hetrocyclic compounds: facile synthesis characterization and bioactivity studies of some substituted -7H-[1,2,4] triazolo[3,4-6][1,3,4]Thiadiazines. Journal of applicable Chemistry 2013; 2(5):10801101.
Dipesh P Mahajan and R.S Bendre: Green synthesis and characterization of some 4substituted-N-aryl-1,3-thiazole-2-amine derivative. Asian Journal of Biochemical and Pharmaceutical Research 2014;2(4): 103-108.
B.P Mallikarjuna, B.S Sastry, G.V Suresh Kumar, Y. Rajendraprasad, S.M Chandrashekar, K Sathish: Synthesis of new 4isopropythiazolehydrazide analogs and some derived clubbed triazole, oxadiazole ring systems. A novel class of potential antibacterial, antifungal and antitubercular agents. European journal of medicinal Chemistry 2009; 1-8.
Ahmed S Aboria, Hamdy M, Abdal Rahman, Nadia M Mahfauz and Mohmoud A ,El Gendy: Novel 5-(2hydroxyphenyl-3substituted-2,3-dihydro-1,3,4 oxadiazole2-thione deivatives: promising anticancer agents. Bioorganic and medical chemistry 2006; 14:1236-1246.
Scherer R, Godoy HT: Effects of extraction methods of phenolic compounds from Xanthium strumarium L and their antioxidant activity. Brazilian journal of medicinal plants 2014; 16(1):41-46.
RozinaParul, Sukalyan Kumar, Kundu and PijushSaha: Invitro nitric oxide scavenging activity of methanol extracts of three Bangladesh medicinal plant. The Pharma Innovation 2012; 1(12) 83-88.
Ruch RJ, Cheng S.J and Klauing JE: Prevention of cytotoxicity and inhibition of intracellular communication by antioxidant catechins isolated from chinese green tea. Carcinogenesis 1989; 10:1003-1008.
Published
How to Cite
Issue
Section
Copyright (c) 2016 Rahul. R, Rakesh Kumar Jat, J. Saravanan
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Journal of Innovations in Pharmaceutical and Biological Sciences is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License. Based on a work at