Liquid chromatographic resolution of 3-amino-1,4-benzodiazepin-2-one derivatives on various Pirkle-type chiral stationary phases.

Abstract:

:The two enantiomers of N-acyl amide and N-ureide derivatives of 3-amino-5-phenyl-1,4-benzodiazepin-2-ones, which have been known to show anti-respiratory syncytial virus (RSV) activity, were resolved on seven different Pirkle-type chiral stationary phases (CSPs) with the use of 10% isopropyl alcohol in hexane as a mobile phase. Among the seven Pirkle-type CSPs, the one based on (S)-leucine derivative named as N-Phe-L-Leu was found to be most successful, the separation factors (α) and the resolutions (R(S) ) for seven analytes being in the range of 1.78-4.21 and 5.94-15.08, respectively. By resolving N-benzyloxycarbonyl derivatives of 3-amino-5-phenyl(or 5-methyl)-1,4-benzodiazepin-2-ones on Pirkle-type CSPs, the phenyl ring at the 5-position and the NH hydrogen at the 1-position of analytes were found to play an important role in the chiral recognition.

journal_name

Chirality

journal_title

Chirality

authors

Park JY,Cho HS,Hyun MH

doi

10.1002/chir.20944

subject

Has Abstract

pub_date

2011-01-01 00:00:00

pages

E16-21

eissn

0899-0042

issn

1520-636X

journal_volume

23 Suppl 1

pub_type

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