Synthesis and biological evaluation of sulfonamide-based 1,3,4-oxadiazole derivatives

S Kavitha,K Kannan,Z Nasarullah

doi:10.4314/bcse.v33i2.11

Abstract

A novel series of 1,3,4-oxadiazole containing sulfonamide derivatives were synthesized by 5-(5-cyclohexyl-1,3,4-oxadiazol-2-yl)-2-methyl-benzenesulfonyl chloride. A good yield of intermediate with various substituted like aryl/hetero was formed. All the synthesized compounds were characterized by FT-IR, 1 H NMR, 13 C NMR and mass spectral studies. These compounds were evaluated for their preliminary bioassay in vitro antimicrobial activity, anti-inflammatory and anti-diabetic activities. In this series, most of the compounds have good anti-inflammatory activity. Particularly, compounds 5c , 5d and 5e showed excellent anti-inflammatory activity with IC 50 values of 110, 110, and 111 μg/mL than diclofenac (157 μg/mL). The frontier orbital energy and the global reactivity descriptor were discussed for the tested compounds using RB3LYP/311G(d,p) basis set. Results revealed that the theoretical calculations of antimicrobial activity were closely related to quantum chemical parameters. KEY WORDS : 1,3,4-Oxadiazole, Sulfonamide, Antimicrobial, Anti-diabetic, Anti-inflammatory, FT, SAR Bull. Chem. Soc. Ethiop. 2019 , 33(2), 307-319. DOI: https://dx.doi.org/10.4314/bcse.v33i2.11

Highlights

Sulfonamides are one of the important drugs in medicinal chemistry, which are effective chemotherapeutic agents against microbial infection in human beings [1]
The results indicated that the presence of halogen, nitro substituted benzene sulfonamide with 1,3,4-oxadiazole moiety showed significant antimicrobial activity. (i) It was observed that fluoro substituted 1,3,4-oxadiazole derivatives were more active compared to chloro and bromo derivatives, followed by derivatives like methoxy, methyl groups respectively [37]. (ii) The presence of electron withdrawing groups and electron donating groups in phenyl ring may enhance antimicrobial activity of the titled compounds [38]. (iii) Hetero aryl ring substituted with 1,3,4-oxdiazole moiety enhances the anti-diabetic activity. (iv) Results revealed that, most of the tested compounds showed good anti-inflammatory activities, due to the presence of hereto substituted aryl ring in the 1,3,4-oxdaizole derivatives
We have synthesized a novel series of 1,3,4-oxadaizole and evaluated for their in vitro antimicrobial activity, anti-inflammatory, antidiabetic activities

Summary

Introduction

Sulfonamides are one of the important drugs in medicinal chemistry, which are effective chemotherapeutic agents against microbial infection in human beings [1]. We have synthesized new 1,3,4-oxadiazole derivatives with sulfonamide and tested for in vitro antimicrobial, antidiabetic, and anti-inflammatory activities. FTIR (KBr) in cm-1: 3053 (NH), 2923, 2853 (CH2 str), 1598 (C=N), 1552 (C=C), 1334 (SO2 str assym), 1162 (SO2 str sym), 1035 (C-O-C), 1H NMR (CDCl3, 300 MHz) δ ppm: 1.36-1.52 (m, 4H), 1.64-1.79 (m, 2H), 1.88-1.92 (m, 2H), 2.13-2.18 (d, 2H), 2.69 (s, 3H), 2.96-3.06 (m, 1H), 6.77-6.82 (m, 1H), 7.35 (d, 1H, J = 9 Hz), 7.40 (d, 1H, J = 8.1 Hz), 7.66-7.72 (m, 1H), 8.09 (d, 1H, J = 7.8 Hz), 8.31 (dd, 1H, J = 6 Hz), 8.78 (s, 1H), 13.9 (s, 1H).

Results

Conclusion