79074-65-0

Upstream product

• 22706-11-2 4-amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione 
• 64-17-5 ethanol 
• 70-11-1 α-bromoacetophenone 
• 3004-42-0 2-Mercapto-5-phenyl-1,3,4-oxadiazole 
• 98-86-2 acetophenone 
• 22706-11-2 3-phenyl-4-amino-5-mercapto-1,2,4-triazole 
• 71-23-8 propan-1-ol 
• 13665-04-8 2,2-dibromoacetophenone 
• 67-56-1 methanol 
• 67-63-0 isopropyl alcohol 
• 532-27-4 1-chloroacetophenone 
• 10364-94-0 1-benzoylimidazole 
• 65-85-0 benzoic acid 
• 613-94-5 benzoic acid hydrazide 

Downstream Products

• 197355-96-7 C₁₆H₁₂N₄ 
• 1083071-81-1 1-acetyl-7-acetylsulfanyl-3,6-diphenyl-1H-pyrazolo[5,1-c][1,2,4]triazole 

Relevant academic research and scientific papers

Preliminary SAR and biological evaluation of antitubercular triazolothiadiazine derivatives against drug-susceptible and drug-resistant Mtb strains

Following up the SAR study of triazolothiadiazoles for their antitubercular activities targeting Mt SD in our previous study, on the principle of scaffold hopping, the C3 and C6 positions of triazolothiadiazine were examined systematically to define a preliminary structure–activity relationship (SAR) with respect to biological activity. This study herein highlights the potential of two highly potent advanced leads 6c-3, 6g-3 and several other compounds with comparable potencies as promising new candidates for the treatment of TB (6c-3, MIC-H37Rv?=?0.25?μg/mL; MIC-MDRTB?=?2.0?μg/mL; MIC-RDRTB?=?0.25?μg/mL; Mt SD-IC50?=?86.39?μg/mL; and 6g-3, MIC-H37Rv?=?1.0?μg/mL; MIC-MDRTB?=?4.0?μg/mL; MIC-RDRTB?=?2.0?μg/mL; Mt SD-IC50?=?73.57?μg/mL). Compounds 6c-3 and 6g-3 possessed a para-nitro phenyl at the 6 position showed low Vero and HepG2 cells toxicity, turning out to be two excellent lead candidates for preclinical trials. In addition, in vitro Mt SD inhibitory assay indicates that Mt SD is at least one of the targets for their antitubercular activity. Thus, they may turn out to be promising multidrug-resistance-reversing agents.

Syntheses of biodynamic heterocycles: baker’s yeast-assisted cyclocondensations of organic nucleophiles and phenacyl chlorides

Substituted phenacyl chlorides (1a–f) were cyclocondensed with nucleophiles thiourea (2a) and thiobenzamide (2b) in presence of baker’s yeast (Saccharomyces cerevisiae) as whole-cell enzyme source in acetonitrile at room temperature to obtain 4-(4-substituted phenyl)thiazol-2-amines (3a–f) and 4-(substituted phenyl)-2-phenylthiazoles (4a–f), respectively. Moreover, substituted phenacyl chlorides also reacted with nucleophiles 2-amino-1,3,4-thiadiazole (2c), o-phenylenediamine (2d), 1-amino-2-mercapto-5-phenyl triazole (2e), and pyridin-2-amine (2f) at room temperature in presence of baker’s yeast to give fused heterocycles 6-(4-substituted phenyl)-2-phenylimidazo[2,1-b][1,3,4]thiadiazoles (5a–f), 2-(4-substituted phenyl)quinoxalines (6a–f), 6-(4-substituted phenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7a–f), and 2-(4-substituted phenyl)H-imidazo[1,2-a]pyridines (8a–f), respectively. The experimental conditions for these cyclocondensations were optimized to obtain the biodynamic heterocycles in high yield. The unique features of this work are use of baker’s yeast as a cheap and readily available natural source of biocatalyst, noticeable rate acceleration, convenient route to products, cost effectiveness, and scalability.

Synthesis and crystal structures of Zn(II)/Co(II) complexes with condensed heterocyclic based 1,2,4-triazole

Three Zn(II)/Co(II) coordination compounds with condensed heterocyclic based 1,2,4-triazole 8H-4, 7-diphenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (L1), and 8H-4-phenyl-7-(pyridine-2-yl)-1,2,4-triazolo[3,4-b]-1,3, 4-thiadiazines (L2), Co(L1)2Cl2 (1), Zn(L1)2Cl2 (2). and Co(L2) 2Cl2 (3) were synthesized and structurally characterized by elemental analyses, IR spectroscopy and single-crystal X-ray diffraction. Complexes 1, 2 and 3 have mononuclear structure, the mononuclear structures of 1 and 2 were further assembled by the C-H...Cl and C-H...N weak interactions into an infinite 2-D supramolecular sheet. Springer Science+Business Media, LLC 2012.

α,α-Dibromoacetophenones mediated synthesis of some new 7H-7-alkoxy-3-alkyl/phenyl-6-aryl-s-triazolo[3,4-b][1,3,4] thiadiazines and their antimicrobial evaluation

Aseriesofnew7H-7-alkoxy-3-alkyl/phenyl-6-aryl-s-triazolo[3,4-b][1,3,4]thiadiazines (3, 4) were synthesized by the reaction of various α,α-dibromoacetophenones 1 with 3-alkyl/phenyl-4-amino-5-mercapto-s-triazoles (2) in different alcoholic solvents in good

Novel method for the synthesis of s -triazolo[3,4- b ][1,3,4]thiadiazines

The reaction of 4-amino-3-mercapto-5-phenyl-s-triazole with aromatic or aliphatic ketones containing active -hydrogens as a methyl or methylene group using an acidified acetic acid method afforded the corresponding s-triazolo[3,4-b][1,3,4]thiadiazines. In

Pyrolytic desulfurization ring contraction of condensed thiadiazines as a general route towards pyrazoloazines and pyrazoloazoles with a bridgehead (ring junction) nitrogen atom

Pyrolytic conversion of [1,2,4]triazino[3,4-b][1,3,4]thiadiazin-4-ones, [1,3,4]thiadiazino[2,3-b]quinazolin-10-ones and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines into their corresponding pyrazolo[5,1-c][1,2,4]triazin-4-ones, pyrazolo[4,3-b]quinazolin-9-on

Bicyclic Compounds Derived from 4-Amino-3-mercapto-1,2,4-triazoles: Facile Routes to 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazines

Treatment of 5-substituted-4-amino-3-mercapto-1,2,4-triazoles (1), with triethyl ortho-formate or acetyl chloride gave the corresponding triazolo[3,4-b]thiadiazoles (2) and (3), respectively. Reaction of (1) with phenacyl bromide, DMAD and DEAD afforded t

SYNTHESIS OF SOME CONDENSED s-TRIAZOLE HETEROCYCLES USING PHASE-TRANSFER CATALYSIS TECHNIQUE

Some condensed heterocyclic systems were obtained by reacting 3-phenyl-4-amino-s-triazole-5-thiol 1 as a dianionic ambident compound containing N- and S- poles with some tetrahalo- and dihalo derivatives as well as α-haloketones and

STUDIES ON 4-AMINO-5-ARYL-1,2,4-TRIAZOLE-3-THIONES

4-Amino-5-aryl-1,2,4-triazole-3-thiones 1 react with phenacylbromide at room temperature to give 2, which could be converted to 3 on reflux. Treatment of 1 with chloroacetonitrile and potassium hydroxide in equimolar ratio and in excess yielded 4 and 6, r

Synthesis of Heterocycles. Part VII . Synthesis and Antimicrobial Activity of Some 7H-s-Triazolothiadiazine and s-Triazolothiadiazole Derivatives

The cyclization of 4-amino-5-aryl-3-cyanomethylthio-1,2,4-triazoles II in the presence of concentrated sulfuric acid yields 7H-6-amino-s-triazolothiadiazines III.Cyclization of 4-amino-5-aryl-1,2,4-triazole-3-thiones I with phenacyl chloride yields 7H-3-aryl-6-phenyl-s-triazolothiadiazines IV.Similarly, compounds I condensed with cyanogen bromide, phenyl isothiocyanate and carbon disulfide to give the corresponding cyclized products 6-amino-3-aryl-s-triazolothiadiazoles V, 3-aryl-6-phenylamino-s-triazolothiadiazoles VI and 3-aryl-s-triazolothiadiazol-6(5H)thiones VII, respectively.Also in the presence of phosphoryl chloride, compounds I underwent cyclization with monocarboxylic acids and oxalic acid to 3,6-diaryl-s-triazolothiadiazole VIII and 6,6'-bis(3-aryl-s-triazolothiadiazoles) IX.The above compounds were screened for their antimicrobial activity.