Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-Arylidene-thiazolidine-2,4-dione Derivatives

Abstract

Derivatives of the thiazolidine-2,4-dione core represent a heterocyclic class with several correlated properties. In this context, the synthesis of structural analogues of these bioactive substances becomes attractive in the field of medicinal chemistry. These analogues act as antimicrobial agents against Gram-positives pathogens. The present work aimed to synthesize 10 different derivatives of 5-arylidene-thiazolidine-2,4-dione, employing urea as the catalyst in a solvent-free reaction medium, with yields that ranged from 45 to 99%. The compounds obtained were submitted to an antimicrobial assay against S. aureus ATCC 29213. Two compounds presented minimum inhibitory concentration of 62.5 and 32.5 μg mL-1 and minimum bactericidal concentration < 500 μg mL-1 , demonstrating their antibacterial potential. Principal component analysis was carried out to discriminate the compounds in active and inactive classes. Four geometric and electronic molecular descriptors were required to completely discriminate the compounds. The selected descriptors can guide us in designing new 5-arylidene-thiazolidine-2,4-dione derivatives with enhanced activity.

Effect of chemical modifications of tannins on their antibiofilm effect against Gram-negative and Gram-positive bacteria

“…Our work provides a clear understanding on which chemical modifications can be made to enhance the activity level or change the activity spectrum of natural tannins, and which chemical modifications are inconvenient for increasing their antibiofilm activity. This is one of the few studies that uses a systematic and statistical analysis to correlate specific chemical characteristics of modified tannins with their antibiofilm activity (38,(74)(75)(76)(77)(78).…”

Diverse 3-Methylthio-4-Substituted Maleimides through a Novel Rearrangement Reaction: Synthesis and Selective Cell Imaging

“…The product was isolated as a yellow solid (734 mg, 78%): mp 209.7–210.4 °C; IR (NaCl, cm –1 ) 3113, 2958, 2749, 1737, 1686, 1593, 1513, 1260, 1180, 1021; 1 H NMR (500 MHz, DMSO- d 6 ) δ 12.51 (br, 1H), 7.74 (s, 1H), 7.55 (d, J = 8.8 Hz, 2H), 7.09 (d, J = 8.8 Hz, 2H), 3.82 (s, 3H); 13 C­{ 1 H} NMR (125 MHz, DMSO- d 6 ) δ 168.0, 167.5, 161.0, 132.1, 131.8, 125.5, 120.3, 114.9, 55.5.…”

“…The product was isolated as a yellow solid (649 mg, 79%): mp 237.0–238.0 °C; IR (NaCl, cm –1 ) 3142, 3034, 2784, 1742, 1689, 1611, 1334, 1166, 760, 683; 1 H NMR (500 MHz, DMSO- d 6 ) δ 12.62 (br, 1H), 7.80–7.79 (m, 1H), 7.61–7.58 (m, 2H), 7.54–7.46 (m, 3H); 13 C­{ 1 H} NMR (125 MHz, DMSO- d 6 ) δ 167.9, 167.3, 133.0, 131.8, 130.4, 130.0, 129.3, 123.5.…”

Synthesis and biological evaluation of thiazolidinedione derivatives with high ligand efficiency to P. aeruginosa PhzS

“…Thiazolidine-2,4-dione derivatives ( 1 − 38 - Tables 1 and 2 ) were obtained by well-established synthetic routes based on Knoevenagel condensation. Compounds 2 31 , 4 32 , 5 33 , 34 , 8–9 7 , 10 35 , 11–17 7 , 18 36 , 19 8 , 22 37 , 38 , 23 39 , 24 35 , 40 , 25 37 , 41 , 42 , 26 43 , 27 43 , 44 , 29 45 , 30 46 , 31 3 , 47 , 32 48 , 33 8 , 35 36 , 37 33 , 49 ( Supplementary material ) were synthesised according to previously published protocols, whereas novel compounds were synthesised through the general steps described in Figure 2 .…”