Different intra- and intermolecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity
The crystal structures of (3S,4aS,8aS)-2-[(2R,3S)-3-benzamido-2-benzoyloxy-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide, C38H47N3O4, (I), and (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-dichlorobenzamido)-2-(2,5-dichlorobenzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide,...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2017-06-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989017007800 |
| _version_ | 1798031275318050816 |
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| author | Wilson Cunico Maria de Lourdes G. Ferreira James L. Wardell William T. A. Harrison |
| author_facet | Wilson Cunico Maria de Lourdes G. Ferreira James L. Wardell William T. A. Harrison |
| author_sort | Wilson Cunico |
| collection | DOAJ |
| description | The crystal structures of (3S,4aS,8aS)-2-[(2R,3S)-3-benzamido-2-benzoyloxy-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide, C38H47N3O4, (I), and (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-dichlorobenzamido)-2-(2,5-dichlorobenzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide, C38H43Cl4N3O4, (II), are described. Despite their chemical similarity, they adopt different conformations in the solid state: (I) features a bifurcated intramolecular 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 intramolecular N—H...O link from the benzamide NH group to the tert-butylamide O atom. In the crystal of (I), molecules 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. |
| first_indexed | 2024-04-11T19:53:46Z |
| format | Article |
| id | doaj.art-6d89959adfa044e0af5f41f16ea596cd |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T19:53:46Z |
| publishDate | 2017-06-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-6d89959adfa044e0af5f41f16ea596cd2022-12-22T04:06:13ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902017-06-0173691391710.1107/S2056989017007800pk2602Different intra- and intermolecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activityWilson Cunico0Maria de Lourdes G. Ferreira1James L. Wardell2William T. A. Harrison3Departamento de Química Orgânica, Universidade Federal de Pelotas (UFPel), Campus Universitário, s/n, Caixa Postal 354, 96010-900 Pelotas, RS, BrazilInstituto de Tecnologia em Fármacos – Farmanguinhos, Fiocruz. R. Sizenando, Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, BrazilInstituto de Tecnologia em Fármacos – Farmanguinhos, Fiocruz. R. Sizenando, Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, BrazilDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, ScotlandThe crystal structures of (3S,4aS,8aS)-2-[(2R,3S)-3-benzamido-2-benzoyloxy-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide, C38H47N3O4, (I), and (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-dichlorobenzamido)-2-(2,5-dichlorobenzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide, C38H43Cl4N3O4, (II), are described. Despite their chemical similarity, they adopt different conformations in the solid state: (I) features a bifurcated intramolecular 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 intramolecular N—H...O link from the benzamide NH group to the tert-butylamide O atom. In the crystal of (I), molecules 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.http://scripts.iucr.org/cgi-bin/paper?S2056989017007800crystal structuremalariaisoquinolinecarboxamidehydrogen bondingaspartyl protease inhibition activity |
| spellingShingle | Wilson Cunico Maria de Lourdes G. Ferreira James L. Wardell William T. A. Harrison Different intra- and intermolecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity Acta Crystallographica Section E: Crystallographic Communications crystal structure malaria isoquinolinecarboxamide hydrogen bonding aspartyl protease inhibition activity |
| title | Different intra- and intermolecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity |
| title_full | Different intra- and intermolecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity |
| title_fullStr | Different intra- and intermolecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity |
| title_full_unstemmed | Different intra- and intermolecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity |
| title_short | Different intra- and intermolecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity |
| title_sort | different intra and intermolecular hydrogen bonding patterns in 3s 4as 8as 2 2r 3s 3 2 5 x2 benzamido 2 2 5 x2 benzoyloxy 4 phenylbutyl n tert butyldecahydroisoquinoline 3 carboxamides x h or cl compounds with moderate aspartyl protease inhibition activity |
| topic | crystal structure malaria isoquinolinecarboxamide hydrogen bonding aspartyl protease inhibition activity |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989017007800 |
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