Studies on Synthesis and Pharmacological Activities of 3,6‐Disubstituted‐1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazoles and Their Dihydro Analogues.

Abstract

Thiadiazole derivatives R 0300Studies on Synthesis and Pharmacological Activities of 3,6-Disubstituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and Their Dihydro Analogues. -Several triazolothiadiazoles (IV) (27 examples) and related dihydro derivatives (VI) (12 examples) are synthesized by condensation of mercaptotriazoles (II) with carboxylic acids or aldehydes, respectively. Some of the products show significant antimicrobial [e.g. (IVd)] or good antiinflammatory and analgesic activities [e.g. (IVf)]. -(MATHEW*, V.; KESHAVAYYA, J.; VAIDYA, V. P.; GILES, D.; Eur. J. Med. Chem. 42 (2007) 6, 823-840; Pharm. Chem., Acharya & B. M. Reddy Coll. Pharm., Bangalore 560 090, India; Eng.) -A. Forchert 42-124

Antiinfective therapy with a small molecule inhibitor of Staphylococcus aureus sortase

“…1 and Table S1). To improve the inhibitory activity, we performed synthetic optimization of the chemical structure of compound 6a (Scheme S1) (16). This synthesis afforded compound 6e [3-(4-pyridinyl)-6-(2-sodiumsulfonatephenyl) [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazole] with an IC 50 of 9.3 μM ( Fig.…”

“…Although not optimized for its pharmacokinetic and pharmacodynamics attributes, compound 6e displayed efficacy as an antiinfective in preventing the lethal outcome of S. aureus bacteremia in mice. Earlier work synthesized a wide variety of 3,6-disubstituted triazolothiadiazole derivatives and examined these compounds for their antibacterial, antifungal, and analgesic attributes (16).…”

“…Although certain members of this class of compounds can inhibit bacterial or fungal growth, antibiotic or analgesic effects are not universal attributes of 3,6-disubstituted triazolothiadiazole compounds (16), which may be explored further for clinical development of antiinfectives (16).…”

Crystal structure of 1H-1,2,4-triazole-3-mercaptoacetic acid, C4H5N3O2S

“…Then the crude product was recrystal-lized from water and the target crystals were subjected to X-ray diffraction analysis. Discussion 1,2,4-Triazole derivatives have been extensively investigated because they possess awide spectrum of chemotherapeutic activities including anti-inflammatory [1,2], anticancer [3], antimicrobial [4][5][6], and antifungal [7]. In fact, some of their derivatives are active constituents of currently used drugs [6].…”

Synthesis of Novel [1,2,4]triazolo[3,4-B][1,3,4]thiadiazole-6(5h)-Thione, 5,8-Dihydro-[1,2,4] Triazolo[4,3-B][1,2,4,5]tetrazine and 5,10-Dihydro -[1,2,4]triazolo[4,3-B][1,2,4] Benzotriazine Derivatives and Study Their Biological Activity.

“…The chemistry of 1,2,4-triazoles and their fused heterocyclic derivatives have received considerable attention owing to their synthetic and effective biological importance. For example, a large number of 1,2,4-triazoles have been incorporated into a wide variety of therapeutically interesting drug candidates possessing antimicrobial [1][2][3][4][5], anti-inflammatory [6], analgesic [7] and anticancer activities [8,9]. Among these heterocycles, the mercapto and thione substituted 1,2,4-triazole ring systems have been well studied and so far a variety of biological activities have been reported for a large number of their derivatives [10,11].…”