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A correlation study of quinoline derivatives and their pharmaceutical behavior by ab initio calculated NQR parameters

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Abstract

In this paper, ab initio calculated NQR parameters for some quinoline-containing derivatives are presented. The calculations are carried out in a search for the relationships between the charge distribution of these compounds and their ability to interact with haematin. On the basis of NQR parameters, π-electron density on the nitrogen atom of the quinoline ring plays a dominant role in determining the ability of quinolines to interact with haematin. This point was confirmed with investigation of Fe+3 cation-π quinoline ring interactions in 2- and 4-aminoquinoline. However, our results do not show any preference for those carbon atoms of the quinoline ring which previous reports have noted. In order to calculate the NQR parameters, the electric field gradient (EFG) should be evaluated at the site of a quadrupolar nucleus in each compound. EFGs are calculated by the Gaussian 98 program using the B3LYP/6-31G* level of theory.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modarres University, P.O. Box 14115-175, Tehran, Iran

    Marjan A. Rafiee & Hossein Naderi-manesh

  2. Department of Chemistry, Tarbiat Modarres University, P.O. Box 14115-175, Tehran, Iran

    Nasser L. Hadipour

Authors
  1. Marjan A. Rafiee
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  2. Nasser L. Hadipour
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  3. Hossein Naderi-manesh
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Correspondence to Nasser L. Hadipour.

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Rafiee, M.A., Hadipour, N.L. & Naderi-manesh, H. A correlation study of quinoline derivatives and their pharmaceutical behavior by ab initio calculated NQR parameters. J Comput Aided Mol Des 18, 215–220 (2004). https://doi.org/10.1023/B:JCAM.0000035201.67977.16

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  • DOI: https://doi.org/10.1023/B:JCAM.0000035201.67977.16

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