Synthesis, Molecular Modeling, and Biological Evaluation of Novel Tetrahydro-β-Carboline Hydantoin and Tetrahydro-β-Carboline Thiohydantoin Derivatives as Phosphodiesterase 5 Inhibitors
Joint Authors
Abadi, Ashraf H.
Lehmann, Jochen
Piazza, Gary A.
Ali, Mohamed S. M.
Abdel-Halim, Mohammad
Source
International Journal of Medicinal Chemistry
Issue
Vol. 2011, Issue 2011 (31 Dec. 2011), pp.1-9, 9 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2011-02-23
Country of Publication
Egypt
No. of Pages
9
Main Subjects
Abstract EN
Two series of fused tetrahydro-β-carboline hydantoin and tetrahydro-β-carboline thiohydantoin derivatives with a pendant 2,4-dimethoxyphenyl at position 5 were synthesized, and chiral carbons at positions 5 and 11a swing from R,R to R,S, S,R, and S,S.
The prepared analogues were evaluated for their capacity to inhibit phosphodiesterase 5 (PDE5) isozyme.
The R absolute configuration of C-5 in the β-carboline hydantoin derivatives was found to be essential for the PDE5 inhibition.
Chiral carbon derived from amino acid even if of the S configuration (L-tryptophan) may lead to equiactive or more active isomers than those derived from amino acid with the R configuration (D-tryptophan).
This expands the horizon from which efficient PDE5 inhibitors can be derived and may offer an economic advantage.
The thiohydantoin derivatives were less active than their hydantoin congeners.
American Psychological Association (APA)
Abadi, Ashraf H.& Lehmann, Jochen& Piazza, Gary A.& Abdel-Halim, Mohammad& Ali, Mohamed S. M.. 2011. Synthesis, Molecular Modeling, and Biological Evaluation of Novel Tetrahydro-β-Carboline Hydantoin and Tetrahydro-β-Carboline Thiohydantoin Derivatives as Phosphodiesterase 5 Inhibitors. International Journal of Medicinal Chemistry،Vol. 2011, no. 2011, pp.1-9.
https://search.emarefa.net/detail/BIM-480951
Modern Language Association (MLA)
Abadi, Ashraf H.…[et al.]. Synthesis, Molecular Modeling, and Biological Evaluation of Novel Tetrahydro-β-Carboline Hydantoin and Tetrahydro-β-Carboline Thiohydantoin Derivatives as Phosphodiesterase 5 Inhibitors. International Journal of Medicinal Chemistry No. 2011 (2011), pp.1-9.
https://search.emarefa.net/detail/BIM-480951
American Medical Association (AMA)
Abadi, Ashraf H.& Lehmann, Jochen& Piazza, Gary A.& Abdel-Halim, Mohammad& Ali, Mohamed S. M.. Synthesis, Molecular Modeling, and Biological Evaluation of Novel Tetrahydro-β-Carboline Hydantoin and Tetrahydro-β-Carboline Thiohydantoin Derivatives as Phosphodiesterase 5 Inhibitors. International Journal of Medicinal Chemistry. 2011. Vol. 2011, no. 2011, pp.1-9.
https://search.emarefa.net/detail/BIM-480951
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-480951