Different intra- and inter-molecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzo-yloxy)-4-phenyl-butyl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity

Wilson Cunico; Maria de Lourdes G Ferreira; James L. Wardell; William T A Harrison

doi:10.1107/S2056989017007800

Different intra- and inter-molecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzo-yloxy)-4-phenyl-butyl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity

Wilson Cunico
, Maria de Lourdes G Ferreira
, James L. Wardell
, William T A Harrison

Chemistry

Universidade Federal de Pelotas
Instituto de Tecnologia em Fármacos, FarManguinhos

Research output: Contribution to journal › Article › peer-review

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Abstract

The crystal structures of (3S,4aS,8aS)-2-[(2R,3S)-3-benzamido-2-benzo-yloxy-4-phenyl-but-yl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamide, C38H47N3O4, (I), and (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-di-chloro-benzamido)-2-(2,5-di-chloro-benzo-yloxy)-4-phenyl-but-yl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamide, C38H43Cl4N3O4, (II), are described. Despite their chemical similarity, they adopt different conformations in the solid state: (I) features a bifurcated intra-molecular N-H⋯(N,O) hydrogen bond from the tert-butylamide NH group to the piperidine N atom and the benzoate O atom, whereas (II) has an intra-molecular N-H⋯O link from the benzamide NH group to the tert-butyl-amide O atom. In the crystal of (I), mol-ecules are linked by C(4) amide N-H⋯O hydrogen bonds into chains propagating in the [010] direction, with both donor and acceptor parts of the benzamide group. In the extended structure of (II), C(11) N-H⋯O chains propagating in the [010] direction arise, with the donor being the tert-butylamide NH group and the acceptor being the O atom of the benzamide group.

Original language	English
Pages (from-to)	913-917
Number of pages	5
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	73
Issue number	6
Early online date	31 May 2017
DOIs	https://doi.org/10.1107/S2056989017007800
Publication status	Published - 1 Jun 2017

Bibliographical note

We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

crystal structure
malaria
isoquinolinecarboxamide
hydrogen bonding
aspartyl protease inhibition activity

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Different intra- and intermolecular hydrogenbonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity
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Cunico, W., Ferreira, M. D. L. G., Wardell, J. L., & Harrison, W. T. A. (2017). Different intra- and inter-molecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzo-yloxy)-4-phenyl-butyl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity. Acta Crystallographica Section E: Crystallographic Communications, 73(6), 913-917. https://doi.org/10.1107/S2056989017007800

Different intra- and inter-molecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzo-yloxy)-4-phenyl-butyl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity. / Cunico, Wilson; Ferreira, Maria de Lourdes G; Wardell, James L. et al.
In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 73, No. 6, 01.06.2017, p. 913-917.

Research output: Contribution to journal › Article › peer-review

Cunico, W, Ferreira, MDLG, Wardell, JL & Harrison, WTA 2017, 'Different intra- and inter-molecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzo-yloxy)-4-phenyl-butyl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity', Acta Crystallographica Section E: Crystallographic Communications, vol. 73, no. 6, pp. 913-917. https://doi.org/10.1107/S2056989017007800

Cunico W, Ferreira MDLG, Wardell JL, Harrison WTA. Different intra- and inter-molecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzo-yloxy)-4-phenyl-butyl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity. Acta Crystallographica Section E: Crystallographic Communications. 2017 Jun 1;73(6):913-917. Epub 2017 May 31. doi: 10.1107/S2056989017007800

Cunico, Wilson ; Ferreira, Maria de Lourdes G ; Wardell, James L. et al. / Different intra- and inter-molecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzo-yloxy)-4-phenyl-butyl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamides (X = H or Cl) : compounds with moderate aspartyl protease inhibition activity. In: Acta Crystallographica Section E: Crystallographic Communications. 2017 ; Vol. 73, No. 6. pp. 913-917.

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abstract = "The crystal structures of (3S,4aS,8aS)-2-[(2R,3S)-3-benzamido-2-benzo-yloxy-4-phenyl-but-yl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamide, C38H47N3O4, (I), and (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-di-chloro-benzamido)-2-(2,5-di-chloro-benzo-yloxy)-4-phenyl-but-yl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamide, C38H43Cl4N3O4, (II), are described. Despite their chemical similarity, they adopt different conformations in the solid state: (I) features a bifurcated intra-molecular N-H⋯(N,O) hydrogen bond from the tert-butylamide NH group to the piperidine N atom and the benzoate O atom, whereas (II) has an intra-molecular N-H⋯O link from the benzamide NH group to the tert-butyl-amide O atom. In the crystal of (I), mol-ecules are linked by C(4) amide N-H⋯O hydrogen bonds into chains propagating in the [010] direction, with both donor and acceptor parts of the benzamide group. In the extended structure of (II), C(11) N-H⋯O chains propagating in the [010] direction arise, with the donor being the tert-butylamide NH group and the acceptor being the O atom of the benzamide group.",

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