Synthesis, biological, and chiroptical activity of 3-phenyl-clavams |
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Authors: | Cierpucha Maciej Solecka Jolanta Frelek Jadwiga Szczukiewicz Patrycja Chmielewski Marek |
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Affiliation: | Institute of Organic Chemistry of the Polish Academy of Sciences, 01-224 Warsaw, Poland. chmiel@icho.edu.pl |
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Abstract: | The [2+2]cycloaddition of chlorosulfonyl isocyanate to simple vinyl ethers derived from the 2-O-sulfonylated (R) and (S) 1-phenyl-1,2-ethanediol leads to 4-alkoxy-azetidin-2-ones with a moderate stereoselectivity. The cycloaddition to analogous (Z)-propenyl ethers proceeds stereospecifically with the retention of the olefin configuration. The intramolecular alkylation of beta-lactam nitrogen atom furnished all possible stereoisomers of 3-phenyl- and 6-methyl-3-phenyl-clavams. The biological and chiroptical activity of synthesized clavams was investigated. The (3R,5R)-diastereomer 30 showed higher inhibition of bacterial enzymes than other related compounds. |
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