Login Register Cart 0
Generic placeholder image

Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1871-5230
ISSN (Online): 1875-614X

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

Synthesis of Some New Hydroxytriazenes and their Antimicrobial and Anti-inflammatory Activities

Author(s): Shilpa Jain, Varsha Dayma, Poonam Sharma, Amit Bhargava, Prabhat K. Baroliya* and Ajay K. Goswami

Volume 19, Issue 1, 2020

Page: [50 - 60] Pages: 11

DOI: 10.2174/1871523018666190301151826

Abstract

Background: Hydroxytriazenes and their derivatives have been studied for the biological and pharmacological applications in the past few years. These compounds possess antibacterial, antifungal, anti-inflammatory, analgesic and wound healing activities. In this study, we report the synthesis of ten hydroxytriazenes in two series derived from disubstituted aniline and studied for antimicrobial and anti-inflammatory activities.

Methods: For this purpose, 2-methyl-5-chloroaniline and 2-trifluoromethyl-5-chloroaniline were used to synthesize compounds A1-5 and B1-5 series, respectively. All compounds were synthesized by the reported method which involves three steps of the method (i) Reduction, (ii) Diazotization, (iii) Coupling. All synthesized compounds were characterized by various techniques CHN elemental analysis, FTIR, 1H NMR, and MASS spectral analysis. The antibacterial activities of the compounds were screened against S. aureus, S. pyogenes, E. coli, P. aeruginosa, and antifungal activities were against C. albicans, A. clavatus by the zone of inhibition method. In addition, anti-inflammatory activity was also evaluated by carrageenan-induced paw edema method and results were reported as % inhibition.

Results: All the synthesized compounds were obtained in pure form and their spectral data are in good agreement with their structure. The synthesized compounds have shown good antimicrobial activity and zone of inhibition was ranging 21 to 24 mm. Further antiinflammatory effect of the compounds was 96.58 to 98.71 % inhibition.

Conclusion: The results of the present study indicate that chloro and trifluoromethyl substitution at hydroxytriazenes skeleton could improve anti-inflammatory and antimicrobial activities.

Keywords: Anti-inflammatory, antibacterial, antifungal, hydroxytriazenes, analgesic, inhibition method.

« Previous Next »
Graphical Abstract

[1]
Palaska, E.; Sahin, G.; Kelicen, P.; Durlu, N.T.; Altinok, G. Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones. Farmaco, 2002, 57(2), 101-107.
[http://dx.doi.org/10.1016/S0014-827X(01)01176-4] [PMID: 11902651]
[2]
Winter, C.A.; Risley, E.A.; Nuss, G.W. Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc. Soc. Exp. Biol. Med., 1962, 111, 544-547.
[http://dx.doi.org/10.3181/00379727-111-27849] [PMID: 14001233]
[3]
Purohit, D.N. Hydroxytriazenes-a review of a new class of chelating agents. Talanta, 1967, 14(3), 353-359.
[http://dx.doi.org/10.1016/0039-9140(67)80009-2] [PMID: 18960104]
[4]
Baroliya, P.K.; Regar, M.; Chauhan, R.S.; Goswami, A.K. Synthesis, characterization and antimicrobial activities of hydroxytriazenes and their Co(II) complexes. Afinidad, 2014, 568, 305-310.
[5]
Choubisa, N.K.; Kodli, K.K.; Panwar, A.K.; Chauhan, R.S.; Goswami, A.K. Biological activities of hydroxytriazenes and their iron complexes. Asian J. Pharm. Res. Dev., 2014, 02, 61-64.
[6]
Kumar, N.; Singh, G.P.; Kumar, A.; Goswami, A.K.; Chauahan, R.S. Biological activities of hydroxytriazenes and their copper complexes. Int. J. Pharm. Res. Scholars, 2014, 3, 153-156.
[7]
Singh, G.P.; Chundawat, N.S.; Goswami, A.K.; Chauhan, R.S. Synthesis and antimicrobial studies of some sulfonate (sodium salt) based hydroxytriazenes and their cobalt(II) complexes. World J. Pharm. Pharm. Sci., 2014, 3(2), 1361-1366.
[8]
Joshi, P.; Pareek, N.; Upadhyay, D.; Khanam, R.; Bhandari, A.; Chauhan, R.S.; Goswami, A.K. Polarographic determination and antifungal activity of Cu (II) complex with 3-hydroxy-3-m-tolyl-1-p-(sulphonamido) phenyltriazene. Int. J. Pharm. Sci. Drug Res., 2010, 2(4), 278-280.
[9]
Goswami, A.K.; Chauhan, R.S.; Sharma, D. Hydroxytriazenes and their Copper(II) complexes: A new class of antibiotic compounds. J. Pharm. Res., 2012, 5(7), 3661-3664.
[10]
Khanam, R.; Jodha, J.S.; Dashora, R.; Goswami, A.K. Antifungal activity of hydroxytriazenes and their ternary complexes with vanadium (V) and thiourea. J. Glob. Pharma Technol., 2014, 6, 1-3.
[11]
Rezaie, B.; Ressalan, S.; Chauhan, R.S.; Goswami, A.K.; Purohit, D.N. Synthesis and insecticidal studies of hydroxytriazenes. Asian J. Chem., 1997, 9, 891-892.
[12]
Kumar, S.; Garg, M.; Jodha, J.S.; Singh, R.P.; Pareek, N.; Chauhan, R.S.; Goswami, A.K. Studies on insecticidal activity of some hydroxytriazene derivatives. Eur. J. Chem., 2009, 6(2), 466-468.
[13]
Ombaka, O.; Gichumbi, J.M. Synthesis and insecticidal activities of some selected hydroxytriazenes. J. Environ. Chem. Ecotoxicol, 2011, 3(11), 286-289.
[14]
Goswami, A.K. Synthesis and insecticidal activity of some hydroxytriazenes and their vanadium complexes. Pestic. Res. J., 2002, 14, 213-215.
[15]
Chauhan, L.S.; Jain, C.P.; Chauhan, R.S.; Goswami, A.K. Synthesis and analgesic activity of hydroxytriazenes. Asian J. Chem., 2007, 19, 4684-4688.
[16]
Chauhan, L.S.; Jain, C.P.; Chauhan, R.S.; Goswami, A.K. Synthesis of some substituted hydroxytriazenes and their analgesic activity. J. Chem. Pharm. Res., 2010, 2(4), 999-1003.
[17]
Singh, K.; Patel, P.; Goswami, A.K. Anti-inflammatory activity of hydroxytriazenes and their vanadium complexes. E-J. Chem., 2008, 5, 1144-1148.
[http://dx.doi.org/10.1155/2008/830737]
[18]
Baroliya, P.K.; Mehta, A.; Dashora, R.; Chauhan, R.S.; Goswami, A.K. Photocatalytic cleavage of hydroxytriazenes: a solid-state synthesis of azo-dyes under sunlight irradiation. Res. Chem. Intermed., 2012, 38, 2149-2153.
[http://dx.doi.org/10.1007/s11164-012-0533-x]
[19]
Isanbor, C.; Hagan, D.O. Fluorine in medicinal chemistry-a review of anti-cancer agents. J. Fluor. Chem., 2006, 2006(127), 303-319.
[http://dx.doi.org/10.1016/j.jfluchem.2006.01.011]
[20]
Karthikeyan, M.S.; Holla, B.S.; Kumari, N.S. Synthesis and antimicrobial studies on novel chloro-fluorine containing hydroxy pyrazolines. Eur. J. Med. Chem., 2007, 42(1), 30-36.
[http://dx.doi.org/10.1016/j.ejmech.2006.07.011] [PMID: 17007964]
[21]
Karthikeyan, M.S.; Prasad, D.J.; Mahalinga, M.; Holla, B.S.; Kumari, N.S. Antimicrobial studies of 2,4-dichloro-5-fluorophenyl containing oxadiazoles. Eur. J. Med. Chem., 2008, 43(1), 25-31.
[http://dx.doi.org/10.1016/j.ejmech.2007.03.013] [PMID: 17521777]
[22]
Shah, P.; Westwell, A.D. The role of fluorine in medicinal chemistry. J. Enzyme Inhib. Med. Chem., 2007, 22(5), 527-540.
[http://dx.doi.org/10.1080/14756360701425014] [PMID: 18035820]
[23]
Wilcken, R.; Zimmermann, M.O.; Lange, A.; Joerger, A.C.; Boeckler, F.M. Principles and applications of halogen bonding in medicinal chemistry and chemical biology. J. Med. Chem., 2013, 56(4), 1363-1388.
[http://dx.doi.org/10.1021/jm3012068] [PMID: 23145854]
[24]
Bamberger, E.; Renauld, E. Über alphylierte und alkylierte Hydroxylamine. Ber. Dtsch. Chem. Ges., 1897, 30, 2278-2289.
[http://dx.doi.org/10.1002/cber.189703002212]
[25]
Elkins, C.M.; Hunter, L. The azo group as a chelating group. J. Chem. Soc., 1938, 1346-1349
[http://dx.doi.org/10.1039/jr9380001346]
[26]
Sogani, N.C.; Bhatacharya, S.C. Preparation and study of hydroxytriazenes as analytical reagents. Ind. Chem. Soc., 1957, 36, 563-566.
[27]
McCracken, W.A.; Cowsan, R.A. Clinical and Oral Microbiology; Hemispher Publishing Corporation: New York, 1983, Vol. 512, .
[28]
Alzoreky, N.S.; Nakahara, K. Antibacterial activity of extracts from some edible plants commonly consumed in Asia. Int. J. Food Microbiol., 2003, 80(3), 223-230.
[http://dx.doi.org/10.1016/S0168-1605(02)00169-1] [PMID: 12423924]
[29]
Rios, J.L.; Recio, M.C.; Villar, A. Screening methods for natural products with antimicrobial activity: a review of the literature. J. Ethnopharmacol., 1988, 23(2-3), 127-149.
[http://dx.doi.org/10.1016/0378-8741(88)90001-3] [PMID: 3057288]
[30]
Esimone, C.O.; Adikwu, M.U.; Okonta, J.M. Preliminary antimicrobial screening of the ethanolic extract from the lichen Usnea subfloridans (L). J. Pharm. Res. Dev., 1998, 3(2), 99-101.
[31]
Aditya, G.N.; Chattopadhyay, R.N.; Mandal, S.; Roy, R.K.; Lahiri, H.L.; Maitra, S.K. Preliminary study on anti-inflammatory effect of calcium channel blockers in albino rats. Int. J. Pharmacol., 1997, 29, 132-134.
[32]
Mahajan, B.K. Significance of difference in mean.Methods in Biostatistics; 5th ed , 1989, pp. 129-153.
[33]
Agarwal, S.; Baroliya, P.K.; Bhargava, A.; Tripathi, I.P.; Goswami, A.K. Synthesis, characterization, theoretical prediction of activities and evaluation of biological activities of some sulfacetamide based hydroxytriazenes. Bioorg. Med. Chem. Lett., 2016, 26(12), 2870-2873.
[http://dx.doi.org/10.1016/j.bmcl.2016.04.051] [PMID: 27136718]
[34]
Cheryl, S. Leung.; Siegfried S. F. Leung; Julian Tirado-Rives; William L. Jorgensen. Methyl Effects on Protein-Ligand Binding. J. Med. Chem., 2012, 55, 4489-450.

Rights & Permissions Print Cite
Article Metrics
17
1
© 2024 Bentham Science Publishers | Privacy Policy