Conformationally restrained β-blocking oxime ethers. 2. Synthesis and β-adrenergic properties of diastereoisomeric anti and syn 2-(5′-(3′-aryl-substituted)isoxazolidinyl)-N-alkylethanolamines☆

Balsamo, Aldo; Breschi, Maria Cristina; Chiellini, Grazia; Lucacchini, Antonio; Macchia, Marco; Martinelli, Adriano; Martini, Claudia; Nardini, C.; Orlandini, Elisabetta; Romagnoli, F.; Rossello, Armando

doi:10.1016/0223-5234(94)90108-2

Cited by 7 publications

(2 citation statements)

References 11 publications

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“…However, the two regioisomers could be easily separated by flash chromatography. Finally, compounds 25 and 26 (Scheme ) were synthesized from the known diastereomeric epoxides 24 , which, in turn, were derived from butadiene monoepoxide . Epoxides 24 were converted to thiiranes 25 with inversion of stereochemistry via a known transformation utilizing thiourea .…”

Section: Resultsmentioning

confidence: 99%

“…Finally, compounds 25 and 26 (Scheme 8) were synthesized from the known diastereomeric epoxides 24, which, in turn, were derived from butadiene monoepoxide. 26 Epoxides 24 were converted to thiiranes 25 with inversion of stereochemistry via a known transformation utilizing thiourea. 27 Epoxides 24 could also be opened with a hydrogen sulfide derivative 28 to give diastereomeric thiol-alcohols 26.…”

Section: Resultsmentioning

confidence: 99%

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Inhibition of the Antibacterial Target UDP-(3-O-acyl)-N-acetylglucosamine Deacetylase (LpxC): Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups

et al. 2002

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UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase (LpxC) is a zinc amidase that catalyzes the second step of lipid A biosynthesis in Gram negative bacteria. Known inhibitors of this enzyme are oxazolines incorporating a hydroxamic acid at the 4-position, which is believed to coordinate to the single essential zinc ion. A new structural class of inhibitors was designed to incorporate a more stable and more synthetically versatile isoxazoline core. The synthetic versatility of the isoxazoline allowed for a broad study of metal binding groups. Nine of 17 isoxazolines, each incorporating a different potential metal binding functional group, were found to exhibit enzyme inhibitory activity, including one that is more active than the corresponding hydroxamic acid. Additionally, a designed affinity label inhibits LpxC in a time-dependent manner.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%