SYNTHESIS AND INVITRO ANTIBACTERIAL SCREENING OF SOME NEW AZOMETHINES DERIVED FROM SULPHONAMIDES
Keywords:Antibacterial screening, Azomethines, Disc diffusion, P aeruginosa, S aureus, B subtilis
Objective: The purpose of research was to synthesize the better antimicrobial compounds using different substituted aromatic aldehydes containing allyl and allyl oxy group are chosen as the starting material for synthesis of imines with sulphonamides helps to formation in presence of alcohol and acidic reagent.
Methods: Reagents used in the present study were of analytical grade and solvents were used after distillation. All the melting points of the synthesized compounds were determined by open capillary and are uncorrected. The purity of the compounds was checked using pre coated TLC plates (MERCK) using n-hexane: ethyl acetate (8:2) solvent system. The developed chromatographic plates were visualized under UV at 254 nm. IR spectra were recorded using KBr on Perkin Elmer spectrophotometer. 1HNMR spectra in DMSO on a BRUKER FT-NMR instrument using TMS as internal standard and chemical shift values were expressed in ppm. Elemental analysis (CHN) was performed on Carlo Erba 1108.
Results: A new series of azomethines was synthesized by condensation of different sulphonamide derivatives with substituted aromatic aldehydes containing allyl and allyloxy group. The structures of these products were confirmed by physical and spectral analysis. The compounds were assayed for antibacterial activity against different human pathogens such as E. coli, P. aeruginosa, S. aureus, B. subtilis. All the compounds exhibited considerable inhibition against the bacteria tested.
Conclusion: Antibacterial activity observed for the synthesized azomethine compounds through the disc diffusion assay. The reference antibacterial drug was Streptomycin and Penicillin-G for E. coli, P. aeruginosa, S. aureus and B. subtilis. Synthesized imines show good biological activity and have the good yield.
Baquero F. Gram-positive resistance: challenge for the development of new antibiotics. J Antimicrob Chemother 1997;39:1â€“6.
Alekshun MN, Levy SB. Molecular mechanisms of antibacterial multidrug resistance. Cell 2007;128:1037â€“50.
Rice LB. Unmet medical needs in antibacterial therapy. Biochem Pharmacol 2006;71:991â€“5.
Hadi JS. Alsalami BK, Essa AH. Microwave assisted one-pot synthesis and screening of some schiff's bases of sulfanilamide. J Sci Res 2009;3:563-8.
Abbas SA, Munir M, Fatima A, Naheed S, Ilyas Z. Synthesis, characterization and biocidal studies of some transition metal complexes containing tetra dentate and neutral bi dentate schiff base. E-J Life Sci 2010;1:37-40.
Kumar S, Niranjan MS, Chaluvaraju KC, Jamakhandi CM, Kadadevar D. Synthesis and antimicrobial study of some schiff bases of sulfonamides. J Curr Pharm Res 2010;01:39-42.
Singh UK, Pandeya SN, Sethia SK, Pandey M, Singh A, Garg A, et al. Synthesis and biological evaluation of some sulfonamide schiffâ€™s bases. IJPSDR 2010;2:216-8.
Kratky M, Sova JV, Volkova M, Buchta V, Trejtnar FS, Rikova J. Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold. Eur J Med Chem 2012;50:433-40.
Suresh R, Kamalakkannan D, Ranganathan K, Arulkumaran R, Sundararajan R, Sakthinathan SP, et al. Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl imines. Spectrochim Acta Part A 2013;101:239â€“48.
Vijesh AM, Isloor AM, Shetty P, Sundershan S, Fun HK. New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobialand analgesic agents. Eur J Med Chem 2013;62:410-5.
Pudota PT, Purohit RSM, Pujar GV. Synthesis, in vitro antimicrobial and cytotoxic activities of some novel bis-1,3,4-oxadiazoles. J Appl Chem Res 2013;7:7-18.
Naganagowda G, Meijboom R, Petsom A. Synthesis and antimicrobial activity of new schiff base compounds containing 2-hydroxy-4-pentadecylbenzaldehyde moiety. Hindawi Publishing Corporation Advances in Chemistry; 2014.
Hussain Z, Yousif E, Altaie A. Synthesis and characterization of Schiff's bases of Sulfamethoxazole. Org Med Chem Lett 2014;4:1.
Soleiman H, Leena Al-Kaabi, Suad A, Yaser T, Rabah I, Naâ€™il S, et al. Antipathogenic effects of structurally-related Schiff base derivatives: Structureâ€“activity relationship. Arabian J Chem 2013;4(1):15.
Hu S, Huang Y, Wu Y, He H, Katherine A, Young G, et al. Structure activity relationship studies of 3-arylsulfonyl-pyrido [1,2-a] pyrimidin-4-imines as potent 5-HT6 antagonists. Bioorg Med Chem 2014;22:1782â€“90.
Asha BT, Rabindra KN, Lata PK, Sunil CH. Synthesis and biological evaluation of Schiffâ€™s bases and 2-azetidinones of isonocotinyl hydrazone as potential antidepressant and nootropic agents. Arabian J Chem. [article in press DOI: 10.1016/j.arabjc.2011.02.015].
Shaoyong K, Yanhong W, Ziwen Y, Kaimei W, Ying L, Liqiao S. Novel cycloalkylthiopheneâ€“imine derivatives bearing benzothiazole scaffold: synthesis, characterization and antiviral activity evaluation. Bioorg Med Chem Lett 2013;23:5131â€“4.
Sriram D, Yogeeswari P, Myneedu NS, Saraswat V. Abacavir prodrugs: microwave-assisted synthesis and their evaluation of anti-HIV activities. Bioorg Med Chem Lett 2006;16:2127-9.
Kumar M, Narasimhan B, Kumar P, Ramasamy K, Mani V, Mishra RK, et al. 4-(1-Aryl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substitutedbenzene sulfonamides: Synthesis, antimicrobial, anticancer evaluation and QSAR studies. Arabian Journal of Chemistry 2013;7(4):436â€“47.
Monteiro A, GonÃ§alves LM, Maria MM, Santos. Synthesis of novel spiropyrazoline oxindoles and evaluation of cytotoxicity in cancer cell lines. Eur J Med Chem 2014;79:266-72.
Aggarwal N, Kumar R, Dureja P, Diwan S, Rawat DS. Schiff bases as potential fungicides and nitrification inhibitors. J Agric Food Chem 2009;57:8520-5.
Isloor AM, Kalluraya B, Shetty P. Regioselective reaction: synthesis, characterization and pharmacological studies of some new Mannich bases derived from 1,2,4-triazoles. Eur J Med Chem 2009;44:3784-7.
Shi L, Ge HM, Tan SH, Li HQ, Song YC, Zhu HL, Tan RX. Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde, Eur J Med Chem 2007;42:558-64.
Wang X, Yin J, Shi L, Zhang G, Song B. Design, synthesis, and antibacterial activity of novel Schiff base derivatives of quinazolin-4(3H)-one. Eur J Med Chem 2014;77:65-74.
Kolundz B, Markovic V, Stanojkovic T, Joksovic L, Matic I, Todorovic N, et al. Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity. Bioorg Med Chem Lett 2014;24:65â€“71.
Ward CE, Berthold RV, Koerwer JF, Tomlin JB, Manning DT. Synthesis and herbicidal activity of 1,2,3,4-tetrahydro-1,3,5-triazino[1,2-a]benzimidazoles. J Agric Food Chem 1986;34:1005-10.
DeMilo AB, Redfern RE. New insect juvenile hormone mimics: aromatic Schiff bases and related compounds against the large milkweed bug and yellow mealworm. J Agric Food Chem 1979;27:760-2.
Gautam N, Chourasia OP. Synthesis, antimicrobial, insecticidal and anthelmintic activity studies of some new alkyl/aryl 6-(4-(4-methyl-1H-1,2,3-triazol-1 yl)phenyl amino) phenyl)-N2,N4-bis(4-methoxyphenyl)-1,3,5-triazin-2,4 diamine carbamic acid ester derivatives. Indian J Chem 2012;51:1020-6.
Gumrukcuoglu N, Sokmen BB, Ugras S, Ugras HI, Yanardag R. Synthesis, antibacterial, antielastase, antiurease and antioxidant activities of new 1, 4-butylene bridged bis-1,2,4-triazole derivatives. J Enzyme Inhib Med Chem 2013;28:89-94.
Bhosale JD, Shirolkar AR, Pete UD, Zade CM, Mahajan DP, Hadole CD, et al. Synthesis, characterization and biological activities of novel substituted formazans of 3,4-dimethyl-1Hpyrrole-2-carbohydrazide derivatives, J Pharm Res 2013;7:582-7.
Sztanke K, Maziarka A, Osinka A, Sztanke M. An insight into synthetic Schiff bases revealing antiproliferative activities in vitro. Bioorg Med Chem 2013;21:3648-66.
Mohana KN, Mallesha L. Synthesis and antiproliferative activity of some new fluorinated Schiff bases derived from 1,2,4-triazoles. J Fluorine Chem 2013;156:15-20.