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Comparison between antioxidant activity of 2,5-disubstituted 1,3,4-oxadiazoles containing heteroaromatic ring and aromatic ring at 2nd position

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Abstract

A series of 4-[5-(substitutedphenyl)-1,3,4-oxadiazol-2-yl]-pyridine) and 2-[5-substitutedphenyl)-1,3,4-oxadiazol-2-yl]-benzenamine derivatives were synthesized from substituted esters and hydrazine hydrate in the presence of ethanol to give isonicotinic acid hydrazide and 2-aminobenzohydrazide followed by reaction with phosphorus oxychloride and various aromatic acids. All the compounds were tested for their in vitro antioxidant activity by 1,1-diphenyl-2-picryl hydrazyl (DPPH) method. Compounds containing aromatic group at 2nd position showed significant activity as compared to standard (ascorbic acid) which concludes that the presence of aromatic group increases the free radical scavenging activity.

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References

  • Chandrashekar J, Karvekar MD (2008) Synthesis of N′-(substituted benzylidene)-1-benzofuran-2-carbohydrazide and 5-(5-substituted-1-benzofuran-2-yl)-1,3,4-oxadiazole-2-thiol as potent antioxidants. Asian J Chem 20:5562–5566

    CAS  Google Scholar 

  • Franski R (2005) Mass spectrometric decompositions of cationized beta-cyclodextrin. Asian J Chem 17:2063–2075

    CAS  Google Scholar 

  • Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR (1989) Vogel’s text book of practical organic chemistry, 5th edn. Longman, UK, pp 1269–1270

    Google Scholar 

  • George S, Parameswaran MK, Chakraborty AR, Kochupappay RT (2008) Synthesis and evaluation of the biological activities of some 3-{[5-(6-methyl-4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3,4-oxadiazol-2-yl]-imino}-1,3-dihydro-2H-indol-2-one derivatives. Acta Pharm 58:119–129

    Article  PubMed  CAS  Google Scholar 

  • Holla BS, Poojary KN, Bhat KS, Ashok M, Poojary B (2005) Synthesis and anticancer activity studies on some 2-chloro-1,4-bis-(5-substituted-1,3,4-oxadiazol-2-ylmethyleneoxy)phenylene derivatives. Indian J Chem 44B:1669–1673

    CAS  Google Scholar 

  • Hussain AA, Ahuja P, Sarafroz (2009) Synthesis and biological evaluation of β-aroylpropionic acid based 1,3,4-oxadiazoles. Indian J Pharm Sci 71(1):62–66

    Article  Google Scholar 

  • Ingole PS, Mohane SR, Berad BN (2007) Synthesis and antimicrobial activity of 2-alkyl/aryl-5-(pyrid-4-yl)-1,3,4-oxadiazoles. Asian J Chem 19:2683–2686

    CAS  Google Scholar 

  • Kamble RR, Sudha BS (2006) Synthesis and pharmacological screening of 5-methyl-3-[p-(6′-aryl-2′-thioxo-1′,2′,5′,6′-tetrahydropyrimidin-4′-yl)-phenyl]-3H-2-oxo-D4-1,3,4-oxadiazoles. Indian J Pharm Sci 68:249–253

    Article  CAS  Google Scholar 

  • Karthikeyan MS, Prasad DJ, Mahalinga M, Holla BS, Kumari NS (2008) Antimicrobial studies of 2,4-dichloro-5-fluorophenyl containing oxadiazoles. Eur J Med Chem 43:25–31

    Article  PubMed  CAS  Google Scholar 

  • Nagalakshmi G (2008) Synthesis, antimicrobial and antiinflammatory activity of 2,5-disubstituted-1,3,4-oxadiazoles. Indian J Pharm Sci 70:1–3

    Article  Google Scholar 

  • Narayana B, Vijayraj KK, Ashalatha BV, Kumari NS (2005) Synthesis of some new 2-(6-methoxy-2-naphthyl)-5-aryl-1,3,4-oxadiazoles as possible non steroidal anti-inflammatory and analgesic agents. Arch der Pharm 338:372–377

    Google Scholar 

  • Omar FA, Mahfouz NM, Rahman MA (1996) Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives. Eur J Med Chem 31:819–825

    Article  CAS  Google Scholar 

  • Pachhamia VL, Parikh AR (1989) Studies on 2,5 disubstituted 1,3,4-oxadiazoles. Part 1: preparation and antimicrobial activity of 2-aryl-5,4-benzenesulphonamidophenyl-4-pyridyl 1,3,4-oxadiazoles. J Indian Chem Soc 66(4):250–251

    CAS  Google Scholar 

  • Padmavathi V, Reddy SN, Mahesh K (2009) Synthesis, antimicrobial and antioxidant activities of sulphone linked bis heterocycled-pyrazolyl oxadiazoles and pyrazolyl thiadiazole. Chem Pharm Bull (Tokyo) 57:1376–1380

    Article  CAS  Google Scholar 

  • Padmavathi V, Reddy SN, Reddy GD, Padmaja A (2010) Synthesis and bioassay of aminosulfonyl-1,3,4-oxadiazoles and their interconversion to 1,3,4-thiadiazoles. Eur J Med Chem 45:4246–4251

    Article  PubMed  CAS  Google Scholar 

  • Rajasekaran S, Rao GK, Pai DPN, Vedavathi J (2010) Microwave assisted synthesis of some 5-pyridyl-2-[(N-substituted phenyl) thioacetamido]-1,3,4-oxadiazoles as antibacterial and antioxidant agents. J Chem Pharm Res 2:101–106

    CAS  Google Scholar 

  • Reddy PSN, Reddy PP (1988) Reaction of 2-aminobenzoylhydrazines with carboxylic-acids—formation of quinazolin-4(H-3)-one, 1,3,4-oxadiazole and 1,3,4-benzotriazepin-5-one derivatives. Indian J Chem 27B:763–765

    CAS  Google Scholar 

  • Somani RR, Shirodkar PY (2008) Synthesis, antibacterial and antitubercular evaluation of some 1,3,4-oxadiazole analogues. Asian J Chem 20:6189–6194

    CAS  Google Scholar 

  • Zarghi A, Tabatabai SA, Faizi M, Ahadian A, Navabi P, Zanganeh V, Shafiee A (2005) Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazole. Bioorg Med Chem Lett 15:1863–1865

    Article  PubMed  CAS  Google Scholar 

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Acknowledgments

One of the authors is thankful to All India Council for Technical Education (AICTE), New Delhi for scholarship. The authors are also thankful to Director, CDRI, Lucknow for spectral analysis.

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Authors and Affiliations

  1. Faculty of Pharmacy, Babu Banarasi Das National Institute of Technology and Management, Dr. Akhilesh Das Nagar, Sector 1, Faizabad Road, Lucknow, 227105, UP, India

    Radhika Maheshwari, Pooja Chawla & Shubhini A. Saraf

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  1. Radhika Maheshwari
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  2. Pooja Chawla
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  3. Shubhini A. Saraf
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Correspondence to Pooja Chawla.

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Maheshwari, R., Chawla, P. & Saraf, S.A. Comparison between antioxidant activity of 2,5-disubstituted 1,3,4-oxadiazoles containing heteroaromatic ring and aromatic ring at 2nd position. Med Chem Res 20, 1650–1655 (2011). https://doi.org/10.1007/s00044-010-9480-5

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