1H-indazole and 2H-indazole derivatives of androsta-5,16-dien-3beta-ol

M. Ramos Silva, V. M. Moreira, C. Cardoso, A. Matos Beja, J. A. R. Salvador

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The title compounds, 17-(1H-indazol-1-yl)androsta-5,16-dien-3beta-ol, (I), and 17-(2H-indazol-2-yl)androsta-5,16-dien-3beta-ol, (II), both C(26)H(32)N(2)O, have an indazole substituent at the C17 position. The six-membered B ring of each compound assumes a half-chair conformation. A twist of the steroid skeleton is observed and reproduced in quantum-mechanical ab initio calculations of the isolated molecule using a molecular orbital Hartree-Fock method. In the 1H-indazole derivative, (I), the molecules are joined in a head-to-head fashion via O-H...O hydrogen bonds, forming chains along the a axis. In the 2H-indazole derivative, (II), the molecules are joined in a head-to-tail fashion with one of the N atoms of the indazole ring system acting as the acceptor. The hydrogen-bond pattern consists of zigzag chains running along the b axis. Substituted steroids have proven to be effective in inhibiting androgen biosynthesis through coordination of the Fe atoms of some enzymes, and this study shows that indazole-substituted steroids adopt twisted conformations that restrict their intermolecular interactions.

LanguageEnglish
Pageso217-o219
Number of pages3
JournalActa Crystallographica Section C: Crystal Structure Communications
VolumeC64
Issue number4
DOIs
Publication statusPublished - 15 Apr 2008

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Indazoles
Derivatives
Steroids
Molecules
Conformations
Hydrogen
Hydrogen bonds
Atoms
Biosynthesis
Molecular orbitals
Skeleton
Androgens
Enzymes

Keywords

  • androstenols
  • hydrogen bonding
  • indazoles
  • molecular structure
  • x-ray diffraction

Cite this

Silva, M. Ramos ; Moreira, V. M. ; Cardoso, C. ; Beja, A. Matos ; Salvador, J. A. R. / 1H-indazole and 2H-indazole derivatives of androsta-5,16-dien-3beta-ol. In: Acta Crystallographica Section C: Crystal Structure Communications. 2008 ; Vol. C64, No. 4. pp. o217-o219.
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1H-indazole and 2H-indazole derivatives of androsta-5,16-dien-3beta-ol. / Silva, M. Ramos; Moreira, V. M.; Cardoso, C.; Beja, A. Matos; Salvador, J. A. R.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. C64, No. 4, 15.04.2008, p. o217-o219.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 1H-indazole and 2H-indazole derivatives of androsta-5,16-dien-3beta-ol

AU - Silva, M. Ramos

AU - Moreira, V. M.

AU - Cardoso, C.

AU - Beja, A. Matos

AU - Salvador, J. A. R.

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N2 - The title compounds, 17-(1H-indazol-1-yl)androsta-5,16-dien-3beta-ol, (I), and 17-(2H-indazol-2-yl)androsta-5,16-dien-3beta-ol, (II), both C(26)H(32)N(2)O, have an indazole substituent at the C17 position. The six-membered B ring of each compound assumes a half-chair conformation. A twist of the steroid skeleton is observed and reproduced in quantum-mechanical ab initio calculations of the isolated molecule using a molecular orbital Hartree-Fock method. In the 1H-indazole derivative, (I), the molecules are joined in a head-to-head fashion via O-H...O hydrogen bonds, forming chains along the a axis. In the 2H-indazole derivative, (II), the molecules are joined in a head-to-tail fashion with one of the N atoms of the indazole ring system acting as the acceptor. The hydrogen-bond pattern consists of zigzag chains running along the b axis. Substituted steroids have proven to be effective in inhibiting androgen biosynthesis through coordination of the Fe atoms of some enzymes, and this study shows that indazole-substituted steroids adopt twisted conformations that restrict their intermolecular interactions.

AB - The title compounds, 17-(1H-indazol-1-yl)androsta-5,16-dien-3beta-ol, (I), and 17-(2H-indazol-2-yl)androsta-5,16-dien-3beta-ol, (II), both C(26)H(32)N(2)O, have an indazole substituent at the C17 position. The six-membered B ring of each compound assumes a half-chair conformation. A twist of the steroid skeleton is observed and reproduced in quantum-mechanical ab initio calculations of the isolated molecule using a molecular orbital Hartree-Fock method. In the 1H-indazole derivative, (I), the molecules are joined in a head-to-head fashion via O-H...O hydrogen bonds, forming chains along the a axis. In the 2H-indazole derivative, (II), the molecules are joined in a head-to-tail fashion with one of the N atoms of the indazole ring system acting as the acceptor. The hydrogen-bond pattern consists of zigzag chains running along the b axis. Substituted steroids have proven to be effective in inhibiting androgen biosynthesis through coordination of the Fe atoms of some enzymes, and this study shows that indazole-substituted steroids adopt twisted conformations that restrict their intermolecular interactions.

KW - androstenols

KW - hydrogen bonding

KW - indazoles

KW - molecular structure

KW - x-ray diffraction

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