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3-Nitroatenolol: First Synthesis, Chiral Resolution and Enantiomers' Absolute Configuration.

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.

SUBMITTER: Sparaco R

PROVIDER: S-EPMC11013601 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature

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3-Nitroatenolol: First Synthesis, Chiral Resolution and Enantiomers' Absolute Configuration.

Sparaco Rosa R Cinque Pierfrancesco P Scognamiglio Antonia A Corvino Angela A Caliendo Giuseppe G Fiorino Ferdinando F Magli Elisa E Perissutti Elisa E Santagada Vincenzo V Severino Beatrice B Luciano Paolo P Casertano Marcello M Aiello Anna A Martins Viegas Gustavo Yuri GY De Nucci Gilberto G Frecentese Francesco F

Molecules (Basel, Switzerland) 20240403 7

4-Nitro and 7-nitro propranolol have been recently synthesized and characterized by us. (±)-4-NO<sub>2</sub>-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, w ...[more]

PMID: 38611877

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