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1.
Org Biomol Chem ; 20(37): 7415-7418, 2022 09 28.
Article in English | MEDLINE | ID: mdl-36102881

ABSTRACT

A novel chiral P,Se-heterodonor ligand has been designed and prepared through an efficient and simple operation. This ligand can be successfully applied to Pd-catalyzed asymmetric allylic substitution with C- and N-nucleophiles, producing a diverse range of chiral allylic products in high yields and enantioselectivities (up to 99% yield and 95% ee).


Subject(s)
Palladium , Catalysis , Ligands , Organophosphorus Compounds , Stereoisomerism
2.
Bioorg Med Chem ; 23(7): 1395-401, 2015 Apr 01.
Article in English | MEDLINE | ID: mdl-25766628

ABSTRACT

To identify new antifungal lead compound based on inhibitors of pyruvate dehydrogenase complex E1, a series of 5-iodo-1,4-disubstituted-1,2,3-triazole derivatives 3 were prepared and evaluated for their Escherichia coli PDHc-E1 inhibitory activity and antifungal activity. The in vitro bioassay for the PDHc-E1 inhibition indicated all the compounds exhibited significant inhibition against E. coli PDHc-E1 (IC50<21µM), special compound 3g showed the most potent inhibitory activity (IC50=4.21±0.11µM) and was demonstrated to act as a competitive inhibitor of PDHc-E1. Meanwhile, inhibitor 3g exhibited very good enzyme-selective inhibition of PDHc-E1 between pig heart and E. coli. The assay of antifungal activity showed compounds 3e, 3g, and 3n exhibited fair to good activity against Rhizoctonia solani and Botrytis cinerea even at 12.5µg/mL. Especially compound 3n (EC50=5.4µg/mL; EC90=21.1µg/mL) exhibited almost 5.50 times inhibitory potency against B. cinerea than that of pyrimethanil (EC50=29.6µg/mL; EC90=113.4µg/mL). Therefore, in this study, compound 3n was found to be a novel lead compound for further optimization to find more potent antifungal compounds as microbial PDHc-E1 inhibitors.


Subject(s)
Antifungal Agents/chemical synthesis , Antifungal Agents/pharmacology , Pyruvate Dehydrogenase (Lipoamide)/antagonists & inhibitors , Triazoles/chemical synthesis , Triazoles/pharmacology , Animals , Pyruvate Dehydrogenase (Lipoamide)/metabolism , Pyruvate Dehydrogenase Complex/antagonists & inhibitors , Pyruvate Dehydrogenase Complex/metabolism , Rhizoctonia/drug effects , Swine
3.
Bioorg Med Chem ; 22(12): 3180-6, 2014 Jun 15.
Article in English | MEDLINE | ID: mdl-24800939

ABSTRACT

By targeting the ThDP binding site of Escherichia coli PDHc-E1, two new 'open-chain' classes of E. coli PDHc-E1 inhibitors, amide and urea derivatives, were designed, synthesized, and evaluated. The amide derivatives of compound 6d, with 4-NO2 in the benzene ring, showed the most potent inhibition of E. coli PDHc-E1. The urea derivatives displayed more potent inhibitory activity than the corresponding amide derivatives with the same substituent. Molecular docking studies confirmed that the urea derivatives have more potency due to the two hydrogen bonds formed by two NH of urea with Glu522. The docking results also indicate it might help us to design more efficient PDHc-E1 inhibitors that could interact with Glu522.


Subject(s)
Amides/chemistry , Drug Design , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/pharmacology , Escherichia coli/drug effects , Molecular Docking Simulation , Pyruvate Dehydrogenase (Lipoamide)/antagonists & inhibitors , Urea/chemistry , Binding Sites , Catalytic Domain , Escherichia coli/enzymology , Hydrogen Bonding , Models, Molecular , Molecular Structure
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