Synthesis and antimicrobial evaluation of new 3-alkyl/aryl-2-[((α,α-diphenyl-α-hydroxy)acetyl)hydrazono]-5-methyl-4-thiazolidinones

Abstract

New 4-thiazolidinone derivatives of benzilic acid (alpha,alpha-diphenyl-alpha-hydroxyacetic acid) have been synthesized and evaluated for antibacterial and antifungal activities. The reaction of 1- (alpha,alpha-diphenyl-alpha-hydroxy)acetyl-4-alkyl/arylthiosemicarbazides with ethyl 2-bromopropionate gave 3-alkyl/aryl-2-[((alpha,alpha-diphenyl-alpha-hydroxy)acetyl)hydrazono]-5-methyl-4-thiazolidinone derivatives. Their antibacterial and antifungal activities were evaluated against S. aureus ATCC 29213, P. aeruginosa ATCC 27853, E. coli ATCC 25922, C. albicans ATCC 10231, C. parapsilosis ATCC 22019, C. krusei ATCC 6258, T. mentagrophytes var. erinacei NCPF 375, M. gypseum NCPF 580 and T. tonsurans NCPF 245. 3e, 3f, 3g and 3h showed the highest antibacterial activity. Particularly 3a and 3e showed the highest antifungal activities against C. parapsilosis ATCC 22019, T. tonsurans NCPF 245 and M. gypseum NCPF 580.

Synthesis and Aldose Reductase Inhibitory Effect of Some New Hydrazinecarbothioamides and 4-Thiazolidinones Bearing an Imidazo[2,1-b]Thiazole Moiety

“…As a continuation of our previous studies on 4-thiazolidinone derivatives with ARIs [37][38][39][40][41][42][43] or different biological activities, [44][45][46][47][48] we report the synthesis of some novel imidazo[2,1-b]thiazole derivatives incorporating two known bioactive nuclei such as hydrazinecarbothioamide or 4-thiazolidinone.…”

Novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group acting as human carbonic anhydrase IX inhibitors

“…The IR spectra exhibited O-H/N-H and C=O bands in the 3226–3567 cm −1 and 1684–1705 cm −1 regions attributed to the common CONH functions of 2 , 3 , and 4 34 , 40 . Observation of new endocyclic C=O bands (1718–1766 cm −1 ) characteristic for such structures besides C=O amide bands (1684–1705 cm −1 ) in the IR spectra of 3 and 4 supported the aimed cyclisation 34 , 40 .…”

“…The 1 H-NMR spectra of 3 and 4 displayed two singlets and two quartettes attributed to the methylene (SCH 2 ) and methane (SC H CH 3 ) ring protons at 5-position of the 4-thiazolidinone system at about δ 4.13–4.24 and 4.39–4.53 ppm, respectively. The C-OH and CONH protons were observed at about δ 6.46–6.81 and δ 10.81–11.55 ppm, respectively 34 , 40 .…”

Synthesis of novel imidazo[1,2-$a$]pyridines and evaluation of their antifungal activities

“…A new C=O band (1720-1697 cm −1 ) in the IR spectra of 5a-f was particularly diagnostic for 4-oxo-1,3-thiazolidine formation. 4−6,10,14,15 Further support was obtained from the 1 H NMR spectra of 5a-f, which showed signals due to the CH 2 protons at the 5 position of 4-oxo-1,3-thiazolidine ring at about 4.22-4.06 ppm 5,6,15,16. After cyclization, the absence of resonances assigned to the N 1 -H and N-H protons of the hydrazinecarbothioamides (4a-f ) provided evidence of 4-oxo-1,3-thiazolidine formation.…”