Facile Synthesis of Azaarene-Substituted Hydroxycoumarins Possessing High Biological Activities via Three-Component C(sp(3))-H Functionalization

Haoxun Dong; Lubin Xu; Shuai-Shuai Li; Liang Wang; Chang-Lun Shao; Jian Xiao

doi:10.1021/acscombsci.6b00082

Facile Synthesis of Azaarene-Substituted Hydroxycoumarins Possessing High Biological Activities via Three-Component C(sp(3))-H Functionalization

ACS Comb Sci. 2016 Sep 12;18(9):604-10. doi: 10.1021/acscombsci.6b00082. Epub 2016 Aug 24.

Authors

Haoxun Dong¹, Lubin Xu¹, Shuai-Shuai Li¹, Liang Wang¹, Chang-Lun Shao², Jian Xiao¹

Affiliations

¹ College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University , Qingdao 266109, China.
² Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, China.

PMID: 27518450
DOI: 10.1021/acscombsci.6b00082

Abstract

An unprecedented three-component C(sp(3))-H functionalization of 2-alkylazaarenes with aryl aldehydes and 4-hydroxycoumarins was realized, providing azaarene-substituted 3-benzyl-4-hydroxycoumarins in good to excellent yields. These new target compounds displayed broad-spectrum antibacterial activities, providing a new type of antibacterial skeleton.

Keywords: 2-alkylazaarenes; 3-benzyl-4-hydroxycoumarins; 4-hydroxycoumarins; C(sp3)−H functionalization; aryl aldehydes; biological activities; three-component.

MeSH terms

4-Hydroxycoumarins / chemical synthesis*
4-Hydroxycoumarins / pharmacology*
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / pharmacology*
Bacillus subtilis / drug effects
Bacteria / drug effects*
Combinatorial Chemistry Techniques
Enterococcaceae / drug effects
Humans
Micrococcaceae / drug effects
Molecular Structure
Staphylococcus epidermidis / drug effects
Stereoisomerism
Structure-Activity Relationship
Vibrio parahaemolyticus / drug effects

Substances

4-Hydroxycoumarins
Anti-Bacterial Agents