Title:Silica gel Supported Boric tri-Sulfuric Anhydride (SiO<sub>2</sub>-BTSA): An Efficient Catalytic System for the Synthesis of Phloroglucide Analogs as Antimicrobial Agents
VOLUME: 18 ISSUE: 4
Author(s):Rahele Bargebid, Ali Khalafi-Nezhad, Kamiar Zomorodian, Mahkameh Moradi and Soghra Khabnadideh*
Affiliation:Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Department of Parasitology, Faculty of Medicine, Shiraz University of Medical Sciences, Shiraz, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz
Keywords:Phloroglucide, polyhydroxyl, SiO2-BTSA, catalyst, antifungal, antibacterial.
Abstract:
Background: Polyhydroxy aromatic compounds are one of the most important classes
of phenolic compounds with different biological activities. Some important and biologically active
phenol-based compounds have also been isolated from nature.
Methods: An efficient procedure for the synthesis of polyhydroxy aromatic compounds (phloroglucide
analogs) is described. In this procedure, a reaction took place between different 4-substituted
phenols and 2,6-bis(hydroxymethyl) phenols. The reactions proceed in the presence of catalytic
amount of silica gel supported boric tri-sulfuric anhydride (SiO2-BTSA) in excellent yields.
Results: 16 compounds were synthesized (I1-I16). Chemical structures of all the compounds were
confirmed by spectroscopic methods. We optimized the chemical reactions in the presence of different
acidic catalysts, different solvents and also different temperatures. A catalytic amount of
SiO2-BTSA in dichloroethane (DCE) was the best condition. Some of the synthesized compounds
were screened for their antimicrobial activities. Antifungal and antibacterial activities of the synthesized
compounds were evaluated by broth microdilution method as recommended by CLSI.
Some of the tested compounds showed good in vitro biological properties.
Conclusion: Our active compounds could introduce as good candidates for further studies as antimicrobial
agents.
