Temperature-Controlled Divergent Synthesis of Pyrazoles and 1-Tosyl-1H-pyrazoles under Transition-Metal-Catalyst- and Oxidant-Free Conditions.

Herein, a general and practical temperature-controlled approach for the divergent synthesis of pyrazoles and 1-tosyl-1H-pyrazoles via electrophilic cyclization in the absence of transition-metal catalysts and oxidants was developed. The desired products were obtained in moderate to excellent yields from common starting materials in both ionic liquids and ethanol by simply tuning the reaction temperature. This strategy employs easily synthesized substrates, mild reaction conditions, and excellent functional-group tolerance.

Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C-H activation.

A regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium catalysis was developed. This transformation tactically linked the 1,2,4-thiadiazoles and succinimides together, and the novel molecules formed may have potential biological activity.

Synthesis and anti-tumor activity of glycosyl oxadiazoles derivatives.

A new series of glycosyl oxadiazoles compounds were synthesized and characterized through (1)H NMR, (13)C NMR, IR and HRMS. The anti-tumor activities for MDA-MB-231 of all these new compounds were screened in vitro by MTT assay. Due to the modification of gastrodin analogues, the anti-tumor activities of these 1,3,4-oxadiazoles derivatives were greatly improved. Six compounds (6 c, 6 d, 6 i, 6 j, 6 k and 6 l) displayed relatively higher MDA-MB-231 potency with IC50 values (0.89, 0.26, 1.35, 3.60, 0.95 and 1.08 µM) compared with the reference medicine Rosiglitazone (5.23 µM).

One-pot chemoenzymatic multicomponent synthesis of thiazole derivatives.

A novel chemoenzymatic one-pot multicomponent synthesis of thiazole derivatives was developed. A series of thiazole derivatives were synthesized with high yields up to 94% under mild enzyme-catalyzed conditions. The blank and control experiments reveal that trypsin from porcine pancreas (PPT) displayed great catalytic activity to promote this reaction and showed a wide tolerance range towards different substrate amines. This trypsin-catalyzed multicomponent conversion method provides a novel strategy to synthesize thiazole derivatives and expands the application of enzymes in organic synthesis.

Metal-free C-3 selective C(sp2)-C(sp3) heteroarylation of anilines with imidazo[1,2-a]pyridine derivatives via cross-dehydrogenative coupling.

A general and straightforward method for the regioselective construction of C-3 heteroaryl-containing imidazo[1,2-a]pyridines via cross-dehydrogenative coupling under transition-metal-free conditions has been reported, utilizing N,N-dimethylaniline as the methylenation source and furnishing the C(sp2)-C(sp3) functionalized products in good to excellent yields. Mechanism studies indicate that a radical pathway is responsible for this transformation.

Suppressive effects of gecko cathelicidin on biofilm formation and cariogenic virulence factors of Streptococcus mutans.

OBJECTIVE: The aims of this study were to investigate the effectivity of gecko cathelicidin Gj-CATH2 on biofilm formation and cariogenic virulence factors of S. mutans, and preliminary explore its function mechanisms. DESIGN: Minimum inhibitory concentration and bacterial killing kinetics assays were performed to assess the antimicrobial effect of Gj-CATH2.The influence of Gj-CATH2 on S. mutans biofilm formation was determined by crystal violet staining method and observed by SEM. The effects of Gj-CATH2 on exopolysaccharides (EPS) synthesis, bacterial aggregation, acidogenicity and aciduricity of S. mutans were also investigated. Quantitative real-time PCR was conducted to acquire the expression profile of related genes. RESULTS: Gj-CATH2 showed strong bactericidal and anti-biofilm effects on S. mutans. SEM confirmed the reduction of the dense structure in S. mutans biofilm in Gj-CATH2-treated groups. Gj-CATH2 significantly inhibited EPS synthesis, cell aggregation, acid production of S. mutans, but showed no influence on its acid proof. Furthermore, the expression of genes related to biofilm formation (gtfB/C/D, gbpB/D), quorum sensing system (luxS and comD/E) and acidogenicity (ldh) was significantly suppressed by Gj-CATH2. Gj-CATH2 also displayed advantageous resistance in human saliva and exhibited negligible toxicity against mammalian cells. CONCLUSIONS: Gj-CATH2 inhibited S. mutans biofilm formation by targeting the bacterial adhesion and the biofilm maturation stages. Gj-CATH2 significantly suppressed virulence factors production of S. mutans, resulting in decreased EPS synthesis and reduced acidogenicity of bacteria. These findings suggest Gj-CATH2 might be a promising agent for clinical application in prevention of dental caries.

Iridium-catalyzed regioselective C-H sulfonamidation of 1,2,4-thiadiazoles with sulfonyl azides in water.

We have developed a regioselective C-N cross-coupling of 1,2,4-thiadiazoles with sulfonyl azides through iridium catalysis in water. This method tactically linked the 1,2,4-thiadiazoles and sulfonamides together, and the novel molecules increased the diversity of 1,2,4-thiadiazoles which may have potential applications.