Fungicide Activity of 5‐(4‐Chlorobenzylidene)‐(Z)‐2‐dimethylamino‐1,3‐thiazol‐4‐one against Cryptococcus Neoformans

Abstract

The present work describes the synthesis and antifungal evaluation of new 5-arylidene-(Z)-2-dimethylamino-1,3-thiazol-4-ones 4a-f, obtained by the reaction of aromatic aldehydes 1 and rhodanine 2 followed by treatment with DMF. All compounds were tested against a panel of yeasts, hialohyphomycetes, and dermatophytes using the microbroth dilution method. Compounds 4a and 4c showed antifungal activity, with compound 4a being the most active one. Compound 4a demonstrated to be fungicidal rather than fungistatic and selective activity against Cryptococcus neoformans and dermatophytes. MIC(100), MIC(80), and MIC(50) of 4a were determined against a panel of clinical isolates of C. neoformans showing ranges of MICs between 2 and 16 microg/mL.

Enantioselective Construction of Vicinal Sulfur‐functionalized Quaternary and Tertiary Stereocenters via Organocatalytic Michael Addition of 5H‐Thiazol‐4‐ones to 1‐Azadienes

“…As a widely exploited pharmacophore, thiazol‐4‐one heterocyclic system has played a key role in medicinal chemistry featuring various bioactivities such as anti‐inflammatory, antifungal, anticancer, antimicrobial, antioxidant as well as antimelanogenic activities . Accordingly, many catalytic methods have been devised in recent years to access thiazol‐4‐one frameworks .…”

Crystal structure of (E)-3-allyl-2-sulfanylidene-5-[(thiophen-2-yl)methylidene]thiazolidin-4-one

“…For pharmacological activities such as antimicrobial and antiinflammatory of arylidene derivatives of rhodanine (2-thioxo-1,3-thiazolidin-4-one), see: Soltero-Higgin et al (2004); Hu et al (2004); Nasr & Said (2003); Johnson et al (2001); Sortino et al (2007); Insuasty et al (2010); Tomasic & Masic (2009 Table 1 Hydrogen-bond geometry (Å , ).…”

“…Rhodanine (2-thioxo-1,3-thiazolidin-4-one) is the key structural feature of a very important group of heterocyclic compounds for drug discovery programs. Arylidene derivatives of rhodanine have attracted great interest for synthetic organic chemists due to the broad biological activities of this class of compounds including antimicrobial (Sortino et al;2007, Hu et al, 2004, anti-inflammatory (Nasr & Said, 2003;Johnson et al 2001), and antifungal (Sortino et al, 2007;Insuasty et al, 2010) properties. Additionally, rhodanine derivatives may potentially be used in the treatment of diabetes, obesity, Alzheimer's disease, cystic fibrosis, thrombocytopenia, cancer, sleep, mood and central nervous system disorders as well as chronic inflammation (Tomasic & Masic, 2009).…”

3-Benzyl-2-(4-fluorophenyl)-1,3-thiazolidin-4-one

“…In our synthetic search for new bioactive compounds, we have recently focused on the preparation of thiazol-4-one derivatives, which have shown a wide range of pharmacological activities (Insuasty et al, 2010, and references therein), i.e. antibacterial, antifungal, antimicrobial, antiviral and anticonvulsant activity.…”