Synthesis and Fungicidal Activity of Novel 4,4‘-Bis(2‘ ‘-aryl-5‘ ‘-methyl/unsubstituted-4‘ ‘-oxo-thiazolidin-3‘ ‘-yl) Bibenzyl

Abstract

Reduction followed by nitration of benzil I yielded 4,4'-dinitrobibenzyl (III) which by reduction furnished quantitatively and analytically pure 4,4'-diaminobibenzyl (IV) which on condensation with different carbonyl compounds gave 4,4'-bis (benzylideneamino) bibenzyls (Va-f). Compounds (Va-f) on cycloaddition with mercaptoacetic acid/2-mercaptopropionic acid yielded the corresponding 4-oxothiazolidin-3-yl bibenzyls (VIa-l). The compounds VIg-l have two chiral centers in each thiazolidinone moiety so two diastereomers are possible, but on crystallization and repeated chromatography, one diastereomer was obtained. The absolute configuration of the diastereomer was tentatively assigned on the basis of (1)H NMR spectra. (1)H NMR spectra of the product showed a distinct doublet at delta 1.22 for C(5)-CH(3) of thiazolidinone ring (22, 23) and a distinct quartet at delta 4.20 for the C(5)-H proton. Similarly, the C(2) proton showed an independent singlet at delta 5.95, so the diastereomers obtained were assigned trans configuration. Compounds Va-f and VIa-l were evaluated in vitro for their fungitoxicities against Fusarium oxysporium and Penicillium citrinum. All the compounds were found to be antifungal active. Some of the compounds displayed activities comparable with that of the commercial fungicide Dithane M-45. Structure-activity relationships for the screened compounds are discussed.

Métodos de obtenção, reatividade e importância biológica de 4-tiazolidinonas

“…No entanto, compostos contendo esse heterociclo possuem grande interesse científico, pois diversos trabalhos relatam um amplo espectro de atividades biológicas dos seus diferentes derivados 7,11,31,57,58 . Como visto anteriormente, o anel 4-tiazolidinona possui vários sítios de substituição, o que leva a um grande número de análogos estruturais.…”

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

“…Thiazolidine and its composites are key components of many natural products and drugs (Fig. 1), and are also present in many synthetic compounds such as anticancer [8][9][10][11], antimicrobial [12][13][14], antitumor [15,16], antidiabetic [17], antiparasitic [18,19], anti-inflammatory [20][21][22], antitubercular [23], antifungal [24], antiviral [25,26], anti-HIV [27][28][29], cytotoxicity [30], antitrypanosomal [31], antinociceptive and anti-hypernociceptive compounds [32]. In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase I [33] and influenza neuraminidase [34], pro-drugs for the treatment of cystinosis [35], radioprotective against γ-irradiation [36] and as S1P1 receptor agonists [37,38] has also been reported.…”

Stereocomplementary Synthesis of cis‐ and trans‐2‐(p‐Bromophenyl)‐5‐methylthiazolidin‐4‐ones: Useful Umpolung‐type Suzuki–Miyaura Cross‐coupling Partner and Donor

“…). Recent representative studies of 1 include the following: (i) 2‐phenyl‐5‐methyl derivative as mycelial growth inhibitor , (ii) 2‐aryl‐5‐(amide methylene) derivatives as C–C chemokine receptor type 4 (CCR4) antagonists , (iii) 2‐aryl‐5‐(amide methylene) derivatives as follicle‐stimulating hormone receptor antagonists , (iv) 2‐aryl‐5‐(carbonyl methylene) derivatives as bacterial and fungal growth inhibitors , and (v) 2‐aryl‐5‐carboxymethyl derivatives as nematicidal agents against Bacillus subtilis, Staphlococcus aureus, and Escherichia coli .…”