Synthesis andin Vitro Antifungal and Cytotoxicity Evaluation of Thiazolo-4H-1,2,4-triazoles and 1,2,3-Thiadiazolo-4H-1,2,4-triazoles

Abstract

The increasing clinical importance of drug‐resistant fungal pathogens has lent additional urgency to microbiological and antifungal research. Various thiazolo(or 1,2,3‐thiadiazolo)thiosemicarbazides (2a—2e), 3‐thiono‐1,4‐dihydrotriazolothiazoles‐(or 1,2,3‐thiadiazoles) (3a—3e), their related substituted thio‐4H‐1,2,4‐triazoles (4a—4p) and sulfones (5a—5o) were synthesized. Most of the compounds tested for antifungal activity exhibited significant effects against Cryptococcus neoofrmans and Sacchromyces cerevisiae at MIC ranges of 0.53 to 12.5μg/mL, whereas their activities were moderate against Candida albicans and weak against Aspergillus fumigatus. At 10 ppm concentration, all compounds showed low toxicity on brine shrimps (higher than 80% survival), except compounds 4c and 2c. At 100 ppm concentration most of the compounds showed toxicity except compounds 2b, 2e, 3c, 3d, 3e, and 4e. Compounds 4b, 4c, and 4h showed in vitro cytotoxicity against Kbalb cell lines and compounds 4c and 4g against 143B cell lines at 0.1 mM concentration.

Crystal structure of {l-benzyI-2-[(4-nitrobenzyI)sulfanyl]-1H-imidazol-5-yl}- methanol, C18H17N3O3S

“…Imidazole derivatives exhibit antibacterial and antifungal activity [1,2]. In recent years there has been increasing interest in the determination of crystal structures for biologically active compounds [3][4][5][6][7][8][9].…”

“…Intermolecular hydrogen bonding between H Abstract C18H17N3O3S, monoclinic, P12i/cl (no. 14), a = 15.705(2) A, b = 12.083(2) A, c = 9.368(1) A, P = 102.404(3)°, V = 1736.3 A 3 , Z = 4, R gl (F) = 0.078, wR^F 2 ) = 0.226, T= 120 K.Source of material {1 -benzyl-2-[(4-nitrobenzyl)sulfanyl]-1 ii-imidazol-5-yl} methanol, was synthesized in accordance with the published procedure [1,2]. Single crystals of the tide compound were prepared from a mixture of n-hexane/dioxan (5:1) at 322 K during five weeks using the branch tube method.…”

Crystal structure of 4-methyl-5-(5-{[5-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-4-phenyl-4H-1,2,4-triazol-3-yl}disulfanyl]-4-phenyl-4H-1,2,4-triazol-3-yl)-2-phenyl-1,3-thiazol acetonitrile, (C36H26N8S4XC2H3N)

“…Thiazolo-l,2,4-triazole derivatives exhibit antibacterial and antifungal activity [1,2]. In the recent years there has been increasing interest in the determination of crystal structures of biologically active compounds [3][4][5][6][7][8][9][10][11][12][13][14], In the crystal structure of title compound, the covalent bonds are found to be normal.…”

“…The title compound was synthesized in accordance with published procedure [ 1,2]. The solution of title compound (0.25 g) in acetonitrile-benzene-methanol (1:1:1, 50 ml) left in room temperature for two weeks.…”

Preparations of diversely substituted thiosemicarbazides and N-hydroxythioureas

“…1 Biologically active thiosemicarbazide derivatives include 1,3,4-thiadiazoles, as antibacterial 2 and antifungal 3 agents, and 1,3,4-thiadiazolium-2-amidines as anticonvulsant, 4 antimicrobial, 5 and antitumor agents. …”