Synthesis and Antifungal Activity of Some 2‐Aryl‐3‐substituted 4‐Thiazolidinones. Synthese und antimykotische Aktivität einiger 2‐Aryl‐3‐substituierter 4‐Thiazolidinone

Abstract

In continuation of our studies on the synthesis and biological activity of 4-thiazolidinone~'.~), we here report the synthesis of some hydrazones and 4-thiazolidinones carrying an imidazo[ 1.2-alpyridine moiety at the Natom, prepared with the objective of screening their antifungal activities. Table 1 The IR-spectra of 2a-h and 3a-h show CO bands at 1640-1580 cm-I (COW-N). A new strong band at 1710 cm-' in the spectra of 3a-h provides f i r m support for ring closure. After the reaction with mercaptoacetic acid the 'H-NMR spectra of compounds 3a-h display two doublets at about 6 = 3.99-3.80 ppm due to the non-equivalence of the methylene protons4). The singlet of N=CH at about 8. 87-8.19 ppm in the spectra of 2a-h is shifted upfield to 6.34-5.77 ppm by the loss of the sp2 character of the involved C-atom. The thiazolidinones exhibit (MH)+ ions (except 3d and 3g) with different intensities (Table 1). Spectral data of respresentative derivatives are given in the Experimental Part. Antifungal activityThe compounds were tested for antifungal activity against Candida albicans ATCC 10231 (A), Microsporum canis (B), Trichophyron menra- grophytes (C), NCPF-3 12 Trichopyron equinum (D). and NCPF-580Microsporum gypseum (E) using the microdilution method5s6). Yeast Nitrogen Base (YNB, Difco) and Nutrient Broth media were used in the tests. Clommazole and miconazole were used as standards. The substances were dissolved in DMSO and solutions of 50-0.04 @nl (for A strain) and 25-0.2 pg/ml (for B, C, D, E strains) were prepared. The minimum concenfration at which no growth was observed was taken as the MIC value (Table 2).

Synthesis of Some New Thiazolidin-5-One Derivatives of Pharmaceutical Interest

“…Diverse biological activities such as bactericidal, 1,2 fungicidal, 3,4 insecticidal, 5,6 anticonvulsant, 7-9 tuberculostatic, 10,11 herbicidal, 12,13 antiviral, 14,15 and antiprotozoal 16 have been found with thiazolidinone derivatives. The diversity of biological and physiological activities of organic sulfur heterocycles may be attributed to the presence of the N C S fragment, which is characteristic of thiazoles, thiazolines, and thiazolidines.…”

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

“…A new strong band at 1764-1713 cm -1 in the spectra of 3a-j provided firm support for ring closure (Cesur et al, 1994). In the 1 H-NMR spectra of compounds 3a-j, NH protons appeared as a singlet (1H) at 11.10-9.91 ppm, the CH-CH 3 protons appeared as a quartet (1H) at 4.68-4.35 ppm and CH-CH 3 protons appeared as a doublet (3H) at 1.72-1.48 ppm which proved the closure of 4-thiazolidinone ring (Farghaly et al, 1990).…”

Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI‐Fe3O4@SiO2 (TMS‐EDTA)

“…1,2,3–Triazole and thiazolone scaffolds have shown various biological activities including; antitumors, [ 1,2 ] anti‐HIV, [ 3 ] anti‐allergy, [ 4 ] antifungal, [ 5–7 ] anti‐infection, [ 8,9 ] anticancer, [ 10 ] antiviral, [ 11–13 ] and antimicrobial properties. [ 14–22 ] Furthermore, the regioselectivity of cycloadducts is crucial [ 23–26 ] and it has been found that some 1,2,3‐triazole and thiazolone derivatives exhibited antityrosinase activity.…”