Synthesis, characterization and antimicrobial activity of novel Schiff base tethered boronate esters of 1,2-O-isopropylidene-α-d-xylofuranose

• Published in: Bioorganic & medicinal chemistry letters 2016-08, Vol.26 (15), p.3447-3452
• Main Authors: Reddy, Eda Rami, Trivedi, Rajiv, Sudheer Kumar, Buddana, Sirisha, Katukuri, Sarma, Akella Venkata Subrahmanya, Sridhar, Balasubramanian, Prakasham, Reddy Shetty
• Format: Article
• Language: English
• Subjects: 1,2-O-Isopropylidene-α-d-xylofuranose; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antifungal activity; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Bacteria - drug effects; Boronate esters; Boronic Acids - chemistry; Boronic Acids - pharmacology; Dose-Response Relationship, Drug; Esters - chemistry; Esters - pharmacology; Fungi - drug effects; Microbial Sensitivity Tests; Molecular Structure; Monosaccharides - chemical synthesis; Monosaccharides - chemistry; Monosaccharides - pharmacology; Schiff base; Schiff Bases - chemical synthesis; Schiff Bases - chemistry; Schiff Bases - pharmacology; Structure-Activity Relationship
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2016.06.049

[Display omitted] A series of twenty one Schiff bases based on boronate ester of 1,2-O-isopropylidene-α-d-xylofuranose scaffold were designed and synthesized by condensation of formyl or amino phenyl boronate esters with substituted anilines or 2-hydroxybenzaldehydes, respectively. All the imines are remarkably stable crystalline solids and were obtained in good yields. All the products were fully characterized by FT-IR, multinuclear NMR (1H, 13C and 11B) spectroscopy, and elemental analysis. Furthermore, the molecular structures of two of the Schiff bases were established by single crystal X-ray diffraction analysis. All the compounds have been screened for in vitro antimicrobial activity against various Gram-positive and Gram-negative bacterial and fungal strains. They exhibited moderate to good inhibitory activity against most of the tested organisms in comparison with standard drugs.