3-Nitroatenolol: First Synthesis, Chiral Resolution and Enantiomers' Absolute Configuration
Rosa Sparaco1, Pierfrancesco Cinque1, Antonia Scognamiglio1
1Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy.
Abstract:
4-Nitro and 7-nitro propranolol have been recently synthesized and characterized by us. (±)-4-NO2-propranolol has been shown to act as a selective antagonist of 6-nitrodopamine (6-ND) receptors in the right atrium of rats. As part of our follow-up to this study, herein, we describe the first synthesis of (±)-3-nitroatenolol as a probe to evaluate the potential nitration of atenolol by endothelium. Chiral chromatography was used to produce pure enantiomers. By using Riguera's method, which is based on the sign distribution of ΔδH, the absolute configuration of the secondary alcohol was determined.
More Related Videos
06:00One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Racemic Mixtures and the Resolution of Enantiomers
Nitrosation of Enols
Prochirality
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Naming Enantiomers
Stereochemical Effects of Enolization
