Login Register Cart 0
Generic placeholder image

Letters in Drug Design & Discovery

Editor-in-Chief

ISSN (Print): 1570-1808
ISSN (Online): 1875-628X

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis, Antioxidant and Anti-inflammatory Activities of 5-((styrylsulfonyl) methyl)-1,3,4-Oxadiazol / Thiadiazol-2-amine Derivatives

Author(s): Gundala Sravya, Ummadi Nagarjuna, Venkatapuram Padmavathi, Galla Rajitha, Sakuri Chandi priya and Adivireddy Padmaja*

Volume 16, Issue 11, 2019

Page: [1233 - 1247] Pages: 15

DOI: 10.2174/1570180816666181102114529

Price: $65

Abstract

Background: A new class of 5-(styrylsulfonylmethyl)-1,3,4-oxadiazol-2-amine and 5- (styrylsulfonylmethyl)-1,3,4-thiadiazol-2-amine derivatives were prepared by derivatization of amino function.

Methods: All the synthesized compounds were tested for antioxidant and anti-inflammatory activities.

Results: The 2-amino-3-chloro-N-(5-(4-methylstyrylsulfonylmethyl)-1,3,4-oxadiazol-2-yl)-propanamide (12b) and 3-chloro-N-(5-(4-methylstyrylsulfonylmethyl)-1,3,4-oxadiazol-2-yl)-butanamide (14b) displayed significant antioxidant activity, greater than the standard Ascorbic acid.

Conclusion: Moreover, 12b and 14b also exhibited promising anti-inflammatory activity.

Keywords: Antioxidant activity, anti-inflammatory activity, semicarbazide, thiosemicarbazide, oxadiazole, thiadiazole.

« Previous Next »
Graphical Abstract

[1]
Rigo, B.; Couturier, D.J. Studies on pyrrolidinones. Synthesis of 5-(5-oxo-2-pyrrolidinyl)-1,3,5-oxadiazole-2-thione deriva-tives. J. Heterocycl. Chem., 1985, 22, 287-288.
[http://dx.doi.org/10.1002/jhet.5570220209]
[2]
Musad, E.A.; Mohamed, R.; Saeed, B.A.; Vishwanath, B.S.; Lokanatha Raia, K.M. Synthesis and evaluation of antioxidant and antibacterial activities of new substituted bis(1,3,4-oxadiazoles), 3,5-bis(substituted) pyrazoles and isoxazoles. Bioorg. Med. Chem. Lett., 2011, 21, 3536-3540.
[3]
Zhou, Y.; Wang, B.; Di, F.; Xiong, L.; Yang, N.; Li, Y.; Li, Y.; Li, Z. Synthesis and biological activities of 2,3-dihydro-1,3,4-oxadiazole compounds and its derivatives as potential activator of ryanodine receptors. Bioorg. Med. Chem. Lett., 2014, 24(10), 2295-2299.
[http://dx.doi.org/10.1016/j.bmcl.2014.03.077] [PMID: 24736118]
[4]
Chandrakantha, B.; Shetty, P.; Nambiyar, V.; Isloor, N.; Isloor, A.M. Synthesis, characterization and biological activity of some new 1,3,4-oxadiazole bearing 2-flouro-4-methoxy phenyl moiety. Eur. J. Med. Chem., 2010, 45(3), 1206-1210.
[http://dx.doi.org/10.1016/j.ejmech.2009.11.046] [PMID: 20004043]
[5]
Suresh Kumar, G.V.; Rajendraprasad, Y.; Mallikarjuna, B.P.; Chandrashekar, S.M.; Kistayya, C. Synthesis of some novel 2-substituted-5-[isopropylthiazole] clubbed 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents. Eur. J. Med. Chem., 2010, 45(5), 2063-2074.
[http://dx.doi.org/10.1016/j.ejmech.2010.01.045] [PMID: 20149496]
[6]
El-Emam, A.A.; Al-Deeb, O.A.; Al-Omar, M.; Lehmann, J. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones. Bioorg. Med. Chem., 2004, 12(19), 5107-5113.
[http://dx.doi.org/10.1016/j.bmc.2004.07.033] [PMID: 15351394]
[7]
Clapp, L.B. Katritzky,(Ed): A. R. Advances in Heterocyclic Chemistry. Academic Press, New York, ; , 1976, 20, pp. 65-116.
[8]
Kumar, D.; Sundaree, S.; Johnson, E.O.; Shah, K. An efficient synthesis and biological study of novel indolyl-1,3,4-oxadiazoles as potent anticancer agents. Bioorg. Med. Chem. Lett., 2009, 19(15), 4492-4494.
[http://dx.doi.org/10.1016/j.bmcl.2009.03.172] [PMID: 19559607]
[9]
Labanauskas, L.; Kalcas, V.; Udrenaite, E.; Gaidelis, P.; Brukstus, A.; Dauksas, V. Synthesis of 3-(3,4-dimethoxyphenyl)-1 H-1,2,4-triazole-5-thiol and 2-amino-5-(3,4-dimethoxyphenyl)-1,3,4-thiadiazole derivatives exhibiting anti-inflammatory activity. Pharmazie, 2001, 56(8), 617-619.
[PMID: 11534336]
[10]
Palaska, E.; Sahin, G.; Kelicen, P.; Durlu, N. T.; Altinok, G. Il. Farmaco. Synthesis and anti-inflammatory activity of 1-acylthio semicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4- triazole-3-thiones 2002, 57, 101-107.
[11]
Nolvi, M.N.; Patel, H.M.; Singh, N.; Gadad, A.K. SCame-otrra, S.; Badiger, A.; Synthesis and anticancer evaluation of novel 2-cyclopropylimidazo [2,1-b] [1,3,4]-thiadiazole deriv-atives Badiger. Eur. J. Med. Chem., 2011, 46, 4411-4418.
[http://dx.doi.org/10.1016/j.ejmech.2011.07.012] [PMID: 21820217]
[12]
Matysiak, J. Evaluation of electronic, lipophilic and membrane affinity effects on antiproliferative activity of 5-substituted-2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles against various human cancer cells. Eur. J. Med. Chem., 2007, 42(7), 940-947.
[http://dx.doi.org/10.1016/j.ejmech.2006.12.033] [PMID: 17320247]
[13]
Zou, X.J.; Zhang, S.W.; Liu, Y.; Liu, Z.M.; Gao, J.W.; Song, Q.L.; Pan, Y.; Zhang, J.Z.; Li, X.J.; Lai, L.H. anti-tumor metastasis and crystal structure of n1-(1,3,4-thiadiazole-2-yl)-n3-m-chlorobenzoyl-urea. Chin. J. Struct. Chem., 2011, 30, 1001-1005.
[14]
Khan, I.; Ali, S.; Hameed, S.; Rama, N.H.; Hussain, M.T.; Wadood, A.; Uddin, R.; Ul-Haq, Z.; Khan, A.; Ali, S.; Choudhary, M.I. Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Eur. J. Med. Chem., 2010, 45(11), 5200-5207.
[http://dx.doi.org/10.1016/j.ejmech.2010.08.034] [PMID: 20828889]
[15]
Du, T.H.; Du, J.H. Synthesis and biological activity of 6-(substituted)-3-(3,4,5-trimethoxyphenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole. Youji Huaxue, 2010, 30, 137-141.
[16]
Li, Q.; Ren, J.; Dong, F.; Feng, Y.; Gu, G.; Guo, Z. Synthesis and antifungal activity of thiadiazole-functionalized chitosan derivatives. Carbohydr. Res., 2013, 373, 103-107.
[http://dx.doi.org/10.1016/j.carres.2013.03.001] [PMID: 23624516]
[17]
Joshi, S.D.; Vagdevi, H.M.; Vaidya, V.P.; Gadaginamath, G.S. Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial and antitubercular agents. Eur. J. Med. Chem., 2008, 43(9), 1989-1996.
[http://dx.doi.org/10.1016/j.ejmech.2007.11.016] [PMID: 18207286]
[18]
Ramana Reddy, M.V.; Reddy, S.; Bhaskar Reddy, D.; Padmavathi, V. Thioglycolates in the synthesis of bis(styryl)-sulfones. Synth. Commun., 1989, 19, 1101-1107.
[19]
Ramana Reddy, M.V.; Reddy, S. A novel synthesis of (E)-substituted styryl(Z) -styryl sulfones. Synthesis, 1984, 13, 322-323.
[http://dx.doi.org/10.1055/s-1984-30827]
[20]
Burits, M.; Bucar, F. Antioxidant Activity of Nigella sativa Essential Oil. Phytother. Res., 2000, 14, 323-328.
[http://dx.doi.org/10.1002/1099-1573(200008)14:5<323:AID-PTR621>3.0.CO;2-Q]
[21]
Cuendet, M.; Hostettmann, K.; Potterat, O.; Dyatmiko, W. Helv. Chim. Acta. 80, 1144-1152 alanosine (NSC 153353), acivicin (NSC 163501), and aminothiadiazole (NSC 4728) in patients with recurrent or metastatic renal cell carcinoma. Invest. New Drugs, 1997, 6, 97-103.
[22]
Ruch, R.J.; Cheng, S.J.; Klaunig, J.E. Prevention of cytotoxicity and inhibition of intercellular communication by antioxidant catechins isolated from Chinese green tea. Carcinogenesis, 1989, 10(6), 1003-1008.
[http://dx.doi.org/10.1093/carcin/10.6.1003] [PMID: 2470525]
[23]
Green, L.C.; Wagner, D.A.; Glogowski, J.; Skipper, P.L.; Wishnok, J.S.; Tannenbaum, S.R. Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids. Anal. Biochem., 1982, 126(1), 131-138.
[http://dx.doi.org/10.1016/0003-2697(82)90118-X] [PMID: 7181105]
[24]
Marcocci, L.; Maguire, J.J.; Droy-Lefaix, M.T.; Packer, L. The nitric oxide-scavenging properties of Ginkgo biloba extract EGb 761. Biochem. Biophys. Res. Commun., 1994, 201(2), 748-755.
[http://dx.doi.org/10.1006/bbrc.1994.1764] [PMID: 8003011]
[25]
Winter, C.A.; Risley, E.A.; Nuss, G.W. Carrageenin-Induced Edema in hind paw of the rat as an assay for antiinflammatory drugs. Proceeding of the society for Biology & Medicine 1962, 111, p. p. 544.

Rights & Permissions Print Cite
Article Metrics
55
2
© 2024 Bentham Science Publishers | Privacy Policy