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

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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 languageEnglish
Pages (from-to)913-917
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume73
Issue number6
Early online date31 May 2017
DOIs
Publication statusPublished - 1 Jun 2017

Fingerprint

Aspartic Acid Proteases
protease
quinoline
Hydrogen bonds
Atoms
hydrogen
Amides
amides
atoms
Benzoates
hydrogen bonds
piperidine
Conformations
Crystal structure
Crystals
quinoline-3-carboxamide
Peptide Hydrolases
solid state
crystal structure
crystals

Keywords

  • crystal structure
  • malaria
  • iso­quinoline­carboxamide
  • hydrogen bonding
  • aspartyl protease inhibition activity

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Physics and Astronomy(all)

Cite this

@article{a6a886fa7ef448bd8861c5c3416ffabe,
title = "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",
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.",
keywords = "crystal structure, malaria, iso­quinoline­carboxamide, hydrogen bonding, aspartyl protease inhibition activity",
author = "Wilson Cunico and Ferreira, {Maria de Lourdes G} and Wardell, {James L.} and Harrison, {William T A}",
note = "We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections.",
year = "2017",
month = "6",
day = "1",
doi = "10.1107/S2056989017007800",
language = "English",
volume = "73",
pages = "913--917",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "6",

}

TY - JOUR

T1 - 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)

T2 - compounds with moderate aspartyl protease inhibition activity

AU - Cunico, Wilson

AU - Ferreira, Maria de Lourdes G

AU - Wardell, James L.

AU - Harrison, William T A

N1 - We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections.

PY - 2017/6/1

Y1 - 2017/6/1

N2 - 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.

AB - 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.

KW - crystal structure

KW - malaria

KW - iso­quinoline­carboxamide

KW - hydrogen bonding

KW - aspartyl protease inhibition activity

U2 - 10.1107/S2056989017007800

DO - 10.1107/S2056989017007800

M3 - Article

C2 - 28638658

VL - 73

SP - 913

EP - 917

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

IS - 6

ER -