Abstract
The synthesis of some novel alkyl/aryl substituted tertiary alcohols was accomplished in two steps. The synthetic route involves preparation of Grignard reagents by treating alkyl/aryl bromides with magnesium turnings in dry ether. Then substituted chalcones were reacted with the Grignard reagents to afford alkyl/aryl substituted tertiary alcohols 1-10. The structures of the synthesized compounds were assigned on the basis of FT-IR, 1H-NMR, 13C-NMR and mass spectroscopic data. The in vivo anti-inflammatory activity of the synthesized compounds was evaluated using the carrageenan-induced hind paw edema method and was compared with that of ibuprofen. Some of the newly synthesized compounds showed promising anti-inflammatory activity. The tertiary alcohols 1-10 were also screened for antibacterial activity against ten bacterial strains using seven Gram-positive and three Gram-negative bacteria and for antifungal activity against Aspergillus Flavus, Aspergillus Niger and Aspergillus pterus. Tertiary alcohols 1-10 were found to exhibit good to excellent antimicrobial activities compared to levofloxacin and fluconazole used as standard drugs.
Highlights
The emergence of multiple-drug resistance organisms, such as methicillin-resistant Staphylococcus aureus and vancomycin resistant Enterococci, has created a major concern in the medical field and an urgent need for new antibacterial agents [1].It is known that hydroxyl groups, amino groups and aromatic rings are general and important functionalities in biologically active compounds [2]
We undertook these studies in order to prepare a novel series of tertiary alcohols to evaluate their anti-inflammatory and antimicrobial activities
The synthetic sequence leading to the alkyl/aryl substituted tertiary alcohols is outlined in Scheme 1
Summary
It is known that hydroxyl groups, amino groups and aromatic rings are general and important functionalities in biologically active compounds [2] With this in mind, we expected that tertiary alcohols with aromatic rings attached to a quaternary carbon atom should display biological activities, since these important functionalities should facilitate the interactions with the relevant receptor molecules [3]. We expected that tertiary alcohols with aromatic rings attached to a quaternary carbon atom should display biological activities, since these important functionalities should facilitate the interactions with the relevant receptor molecules [3] Along these lines the potent broad-spectrum antifungal activities of two new enantiopure tertiary alcohols having fluoro-substituted aromatic rings has been reported [4]. Tertiary butyl alcohol can be applied in the preparation of a hydrophobic drug-hydroxypropyl B-cyclodextrin complex of ketoprofen and nitrendipine, increasing the solubility of the drugs in both simulated gastric juice and in simulated intestinal fluid, which improves the absorption and pharmacodynamic properties of drugs [10]
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