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Keywords:

  • chiral stationary phase;
  • enantiomer separation;
  • liquid chromatography;
  • 3-amino-1,4-benzodiazepin-2-one derivatives

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 (RS) 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[BOND]H hydrogen at the 1-position of analytes were found to play an important role in the chiral recognition. Chirality, 2011. © 2011 Wiley Periodicals, Inc.

Featured Compounds

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  1. 1 - 15
Compound 1a
Molecular Weight:385.4153
Molecular Formula:C23H19N3O3
InChIKey:SJZIESNYFPDCPM-UHFFFAOYSA-N
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Compound 1b
Molecular Weight:464.311
Molecular Formula:C23H18BrN3O3
InChIKey:GZXPABLIRBKWQN-UHFFFAOYSA-N
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Compound 1c
Molecular Weight:419.86
Molecular Formula:C23H18ClN3O3
InChIKey:LEMIDUQNFRDMBF-UHFFFAOYSA-N
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Compound 1d
Molecular Weight:419.86
Molecular Formula:C23H18ClN3O3
InChIKey:JZQHSKKXGOVQPA-UHFFFAOYSA-N
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Compound 1e
Molecular Weight:323.3459
Molecular Formula:C18H17N3O3
InChIKey:AXWZQHIFAVSNPX-UHFFFAOYSA-N
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Compound 1f
Molecular Weight:399.4418
Molecular Formula:C24H21N3O3
InChIKey:MDJBOXIEVUNHJB-UHFFFAOYSA-N
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Compound 1g
Molecular Weight:413.4684
Molecular Formula:C25H23N3O3
InChIKey:SVDWZEFEXCKGFU-UHFFFAOYSA-N
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Compound 1h
Molecular Weight:475.5378
Molecular Formula:C30H25N3O3
InChIKey:SPTTUBMUJMPTAM-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:293.3199
Molecular Formula:C17H15N3O2
InChIKey:MMXSDWJOQSEPSM-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:361.4369
Molecular Formula:C22H23N3O2
InChIKey:RYSKFDQMKULSGP-UHFFFAOYSA-N
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Compound 2c
Molecular Weight:355.3893
Molecular Formula:C22H17N3O2
InChIKey:QFKKCJIHGIAESG-UHFFFAOYSA-N
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Compound 2d
Molecular Weight:345.3514
Molecular Formula:C20H15N3O3
InChIKey:GLKYCYCXGFCQDV-UHFFFAOYSA-N
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Compound 2e
Molecular Weight:361.417
Molecular Formula:C20H15N3O2S
InChIKey:OGYWKBJFCNOLNS-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:370.4039
Molecular Formula:C22H18N4O2
InChIKey:GFJBDSSLKCOLIE-UHFFFAOYSA-N
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Compound 3b
Molecular Weight:388.3944
Molecular Formula:C22H17FN4O2
InChIKey:MTPVBMVUENFFLL-UHFFFAOYSA-N
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