6‑Hydroxymethyl Indolizidin-2-one Amino Acid Synthesis, Conformational Analysis, and Biomedical Application as Dipeptide Surrogates in Prostaglandin‑F2α Modulators

6-Hydroxymethyl indolizidin-2-one amino acids were synthesized in 10 steps from l-serine by intramolecular ring opening of a symmetrical epoxide and lactam formation. X-ray analyses indicated the bicycles replicated ideal peptide type II′ β-turn central dihedral angle geometry. Inside a prostaglandi...

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Bibliographic Details
Published in:Organic letters 2021-07, Vol.23 (13), p.5192-5196
Main Authors: Mulamreddy, Ramakotaiah, Hou, Xin, Chemtob, Sylvain, Lubell, William D
Format: Article
Language:English
Online Access:Get full text
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Summary:6-Hydroxymethyl indolizidin-2-one amino acids were synthesized in 10 steps from l-serine by intramolecular ring opening of a symmetrical epoxide and lactam formation. X-ray analyses indicated the bicycles replicated ideal peptide type II′ β-turn central dihedral angle geometry. Inside a prostaglandin-F2α receptor modulator, the 6-hydroxymethyl analogue retained inhibitory activity on myometrial contractility.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01733