Synthesis, characterization, spectroscopic studies and biological evaluation of Schiff bases derived from 1–hydroxy-2-acetonapthanone

The four Schiff bases (I - IV) were synthesized by the condensation reaction of 1(1-hydroxynaphthalen-2-yl)ethanone, 1-(4-chloro-1hydroxynaphthalen-2-yl)ethanone and 1-(4-bromo-1-hydroxynaphthalen-2-yl)ethanone with propane-1,3-diamine and pentane-1,3-diamine. The structural analysis is done by UVvi...

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Bibliographic Details
Main Authors: B.T. Vhanale, N.J. Deshmukh, A.T. Shinde
Format: Article
Language:English
Published: Elsevier 2019-11-01
Series:Heliyon
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S2405844019364345
Description
Summary:The four Schiff bases (I - IV) were synthesized by the condensation reaction of 1(1-hydroxynaphthalen-2-yl)ethanone, 1-(4-chloro-1hydroxynaphthalen-2-yl)ethanone and 1-(4-bromo-1-hydroxynaphthalen-2-yl)ethanone with propane-1,3-diamine and pentane-1,3-diamine. The structural analysis is done by UVvis., FT-IR, 1H NMR, 13C NMR, LCMS and elemental analyses. These compounds were assayed for antibacterial (Escherichia coli and Salmonella Typhi) activity and antioxidant (2,2-Diphenyl-1-Picryl Hydrazyl(DPPH) and Hydroxyl radical scavenging method) activity. The antibacterial and antioxidant activities of synthesized Schiff bases exhibited better degrees of inhibitory effects. Among these, Schiff base 2,2'-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(4-chloronaphthalen-1-ol) (II) exhibited excellent antibacterial activity with MICs of 0.12, 0.25, 0.5 and 1 mg/ml against E. coli and Salmonella Typhi. Furthermore, two Schiff bases such as, 2,2'-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(naphthalen-1-ol) (I) and 2,2'-((pentane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(4-bromonaphthalen-1-ol) (IV) exhibited promising antioxidant activity.
ISSN:2405-8440