1,3,4-Thiadiazole and 1,2,4-triazole-3(4 H )-thione bearing salicylate moiety: synthesis and evaluation as anti- Candida albicans

Abstract

Dramatically increased occurrence of both superficial and invasive fungal infections has been observed. Candida albicans appear to be the main etiological agent of invasive fungal infections. The anti-C. albicans activity of thiosemicarbazide, 1,3,4-Thiadiazole, and 1,2,4-triazole-3(4H)-thione compounds (compounds 3-23) were investigated. The MIC values of thiadiazole and triazole derivatives 10-23 were in the range of 0.08-0.17 µmol mL -1 , while that of fluconazole was 0.052 µmol mL -1 . Compound 11 (5-(2-(4-chlorobenzyloxy)phenyl)-N-allyl-1,3,4-thiadiazol-2-amine) and compound 18 (5-(2-(4-chlorobenzyloxy)phenyl)-4-allyl-2H-1,2,4-triazole-3(4H)-thione) were found to be the most active compounds, with MIC values of 0.08 µmol mL -1 . The newly synthesized thiadiazole and triazole compounds (compounds 10-23) showed promising anti-Candida activity. The allyl substituent-bearing compounds 11 and 18 exhibited significant anti-Candida albicans activity and showed a binding mode as well as the fluconazole x-ray structure.Uniterms: Anti-Candida/docking studies. Thiadiazole. Triazole.

One-Pot Synthesis of Some New s-Triazole Derivatives and Their Potential Application for Water Decontamination

“…In recent years, s -triazoles and their fused heterocyclic derivatives have received much interest due to their effective medicinal importance. There are many marked drugs, such as triazolam, alprazolam, and etizolam, containing the s -triazole group. − In the past decade, several applications of heterocyclic compounds containing nitrogen atoms have been reported. − Biological activities; biomedical uses; and commercial applications such as dyes, insecticides, and herbicides of s -triazoles linked to heterocyclic rings have also been demonstrated. − Recently, derivatives carrying the s -triazole moiety possess a wide spectrum of chemotherapeutic activities including antiviral, antifungal, , anthelmintic, antitumor, − antibacterial, anti-inflammatory, − antitubercular, analgesic, , antipyretic, , and anticancer activities . Indeed, some of these derivatives were actually active ingredients of drugs .…”

Synthesis of 1,3,4-Thiadiazole Derivatives and Microbiological Activities: A Review

“…The authors inserted these substituents at the C-2 position of the thiadiazole ring in order to enhance the lipophilicity and subsequently the biological activity of the compounds. 82 The compounds (103a-g) had MIC values in the range of 0.08 to 0.17 µmol/mL and showed variable and promising anti-Candida albicans activity. The compound 103b was found to be the most active, with a MIC value of 0.08 µmol/mL.…”

“…For optimization of antifungal activity and in view of the results, the author suggests that further studies be undertaken starting with the compound 103b. 82 Upadhyay and Mishra (2017) 22 performed microbial studies of 1,3,4-thiadiazoles (104ah) by the disc diffusion technique and minimum inhibitory concentration (MIC). The compounds were tested against Gramnegative bacteria, Escherichia coli, Bacillus subtilis and Pseudomonas aeruginosa, Grampositive bacterium, Staphylococcus aureus and the fungi Aspergillus niger and Candida albicans.…”

Synthesis and Evaluation of New 1,3,4-Thiadiazole Derivatives as Potent Antifungal Agents

“…Imidazole- and triazole-based synthetic antifungal drugs prevent the conversion of lanosterol to ergosterol and inhibit the enzyme cytochrome P450 14-α-demethylase enzyme [13,22,23,24,25,26,27]. Based on the bioisosterism and antifungal potency of azole-type compounds, researchers reported several studies including thiadiazole derivatives and their antifungal activity [28,29,30]. From this point of view, in our previous paper, we reported the synthesis and antifungal activity evaluation of some oxadiazole–thiadiazole derivatives, which target the P450 14-α-demethylase enzyme [28].…”