Synthesis and NK(1)/NK(2) binding activities of a series of diacyl-substituted 2-arylpiperazines.
Publication
, Journal Article
Blythin, DJ; Chen, X; Piwinski, JJ; Shih, N-Y; Shue, H-J; Anthes, JC; McPhail, AT
Published in: Bioorganic & medicinal chemistry letters
November 2002
The synthesis and binding affinity for hNK(1) and hNK(2) receptors of a series of diacyl substituted 2-aryl piperazines are described. SAR evaluation led to the racemic derivative 11g as an apparent dual inhibitor. Chiral chromatographic separation of 11g led to the observation that NK(1) activity was shown by one enantiomer (13a) and NK(2) activity was shown by the other enantiomer (13b). X-ray crystallographic analysis of the crystalline di-BOC derivative of the NK(2) active piperazine (15) showed that the 2R configuration was associated with NK(2) activity. Further derivatization indicated that dual NK(1)/NK(2) activity could be built into the 2R series.
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Published In
Bioorganic & medicinal chemistry letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
November 2002
Volume
12
Issue
21
Start / End Page
3161 / 3165
Related Subject Headings
- Vas Deferens
- Trachea
- Structure-Activity Relationship
- Stereoisomerism
- Receptors, Neurokinin-2
- Receptors, Neurokinin-1
- Piperidines
- Piperazines
- Molecular Conformation
- Models, Molecular
Citation
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Blythin, D. J., Chen, X., Piwinski, J. J., Shih, N.-Y., Shue, H.-J., Anthes, J. C., & McPhail, A. T. (2002). Synthesis and NK(1)/NK(2) binding activities of a series of diacyl-substituted 2-arylpiperazines. Bioorganic & Medicinal Chemistry Letters, 12(21), 3161–3165. https://doi.org/10.1016/s0960-894x(02)00645-5
Blythin, David J., Xiao Chen, John J. Piwinski, Neng-Yang Shih, Ho-Jane Shue, John C. Anthes, and Andrew T. McPhail. “Synthesis and NK(1)/NK(2) binding activities of a series of diacyl-substituted 2-arylpiperazines.” Bioorganic & Medicinal Chemistry Letters 12, no. 21 (November 2002): 3161–65. https://doi.org/10.1016/s0960-894x(02)00645-5.
Blythin DJ, Chen X, Piwinski JJ, Shih N-Y, Shue H-J, Anthes JC, et al. Synthesis and NK(1)/NK(2) binding activities of a series of diacyl-substituted 2-arylpiperazines. Bioorganic & medicinal chemistry letters. 2002 Nov;12(21):3161–5.
Blythin, David J., et al. “Synthesis and NK(1)/NK(2) binding activities of a series of diacyl-substituted 2-arylpiperazines.” Bioorganic & Medicinal Chemistry Letters, vol. 12, no. 21, Nov. 2002, pp. 3161–65. Epmc, doi:10.1016/s0960-894x(02)00645-5.
Blythin DJ, Chen X, Piwinski JJ, Shih N-Y, Shue H-J, Anthes JC, McPhail AT. Synthesis and NK(1)/NK(2) binding activities of a series of diacyl-substituted 2-arylpiperazines. Bioorganic & medicinal chemistry letters. 2002 Nov;12(21):3161–3165.
Published In
Bioorganic & medicinal chemistry letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
November 2002
Volume
12
Issue
21
Start / End Page
3161 / 3165
Related Subject Headings
- Vas Deferens
- Trachea
- Structure-Activity Relationship
- Stereoisomerism
- Receptors, Neurokinin-2
- Receptors, Neurokinin-1
- Piperidines
- Piperazines
- Molecular Conformation
- Models, Molecular