Spectroscopic characterization, antimicrobial activity and molecular docking study of novel azo-imine functionalized sulphamethoxazoles
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[SMX—N=N—C6H3—(p-OH)(m—CHO)] ( 1 ) reacts with ArNH2 to synthesize Schiff bases, [SMX—N=N—C6H3—(pOH)(m—HC=N—Ar)] (Ar =—C6H5 ( 2a ), —C6H4—p—CH3 ( 2b ), —C6H4—p—OCH3 ( 2c ), —C6H4—p—Cl ( 2d ), —C6H4—p—NO2 ( 2e ), —C10H7 ( 2f )) and the products have been assessed for antibacterial properties against Gram positive bacteria, B. subtillis: IC50 (μg/ml): 39.2 ( 1 ), 60.1 ( 2a ), 64.0 ( 2b ), 85.6 ( 2c ), 55.1 ( 2d ), 88.4 ( 2e ) and 65.1 ( 2f ); and Gram negative bacteria, E. coli: IC50 (μg/ml): 159.0 ( 1 ), 151.4 ( 2a ), 155.3 ( 2b ), 140 ( 2c ), 156.0 ( 2d ), 153.5 ( 2e ) and 157 ( 2f ). The cell line toxicity (Vero cells) has also been evaluated with these compounds and EC50 (μg/ml) values are 129.9 ( 1 ), 74.2 ( 2a ) and 93.0 ( 2b ), 191.9 ( 2c ), 99.1 ( 2d ), 93.2 ( 2e ) and 62.0 ( 2f ). The anti-viral efficiency against harpies virus (HSV1F ATCC-733) infection demonstrates that the compound 1 has highest selectivity index (CC50/EC50), 5.06 than the compounds 2a-f (CC50/EC50: 1.18 ( 2a ), 1.42 ( 2b ), 3.50 ( 2c ), 1.45 ( 2d ), 1.58 ( 2e ), 1.29 ( 2f )). The compounds have been spectroscopically characterized and the structural confirmation has been established in one case by single crystal X-ray diffraction studies of 2c . In silico Molecular Docking study has been done using optimized geometries of the compounds to search the most favored binding mode of these drugs and hence useful to explain their competitive drug efficiency.
Sahu , N , Mondal , S , Naskar , K , Mahapatra , A D , Gupta , S , Slawin , A M Z , Chattopadhyay , D & Sinha , C 2018 , ' Spectroscopic characterization, antimicrobial activity and molecular docking study of novel azo-imine functionalized sulphamethoxazoles ' , Journal of Molecular Structure , vol. 1155 , pp. 152-164 . https://doi.org/10.1016/j.molstruc.2017.10.040
Journal of Molecular Structure
© 2017 Elsevier Ltd. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.molstruc.2017.10.040
DescriptionFinancial support from University Grants Commission (F.42-333/2013(SR)) and the Council of Scientific and Industrial Research (01(2894)/09/EMR-II), New Delhi are gratefully acknowledged.
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