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

Authors

  • Je Young Park,

    1. Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, South Korea Contribution to the Proceedings of the 22nd International Symposium on Chirality [ISCD 22]
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  • Hwan Sun Cho,

    1. Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, South Korea Contribution to the Proceedings of the 22nd International Symposium on Chirality [ISCD 22]
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  • Myung Ho Hyun

    Corresponding author
    1. Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, South Korea Contribution to the Proceedings of the 22nd International Symposium on Chirality [ISCD 22]
    • Department of Chemistry, Pusan National University, Busan 609-735, Republic of Korea

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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.

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