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'Click' D(1) receptor agonists with a 5-HT(1A) receptor pharmacophore producing D(2) receptor activity.
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- Author(s): Zhang J;Zhang J; Zhang H; Cai W; Yu L; Zhen X; Zhang A
- Source:
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2009 Jul 15; Vol. 17 (14), pp. 4873-80. Date of Electronic Publication: 2009 Jun 16.
- Publication Type:
Journal Article; Research Support, Non-U.S. Gov't
- Language:
English
- Additional Information
- Source:
Publisher: Elsevier Science Country of Publication: England NLM ID: 9413298 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1464-3391 (Electronic) Linking ISSN: 09680896 NLM ISO Abbreviation: Bioorg Med Chem Subsets: MEDLINE
- Publication Information:
Publication: Oxford : Elsevier Science
Original Publication: Oxford : New York : Pergamon Press, c1993-
- Subject Terms:
- Abstract:
A series of new 1-aryl-3-benzazepine derivatives containing an arylpiperazinyl function as the N3 substituent were synthesized by combining a D(1) receptor agonistic pharmacophore and a 5-HT(1A) receptor pharmacophore through Click reaction. Interestingly, these compounds generally do not have good binding affinity at the D(1) receptor, but most compounds are potent at both D(2) and 5-HT(1A) receptors. Compound 8h, containing 1-m-tolyl-benzazepine scaffold and 2-methoxyphenylpiperazine core, displayed good affinity at all tested receptors, with K(i) values of 144, 80, and 133nM, for the D(1), D(2), and 5-HT(1A) receptors, respectively. Compound 13 with the triazole moiety formed differently from that in 8h showed the highest affinity at the D(2) receptor with K(i) value of 19nM. This compound also showed moderate affinity at the 5-HT(1A) (K(i), 105nM), and D(1) (K(i), 551nM) receptors. Functional assays indicated that both compounds 13 and 8h are antagonists at D(1) and D(2) receptors, whereas full agonistic activity at the 5-HT(1A) receptor was observed. In agreement with the binding affinity, compound 13 is a high efficacy D(2) antagonist and 5-HT(1A) agonist.
- Accession Number:
0 (Benzazepines)
0 (Dopamine D2 Receptor Antagonists)
0 (Piperazines)
0 (Receptors, Dopamine D1)
0 (Receptors, Dopamine D2)
0 (Serotonin 5-HT1 Receptor Agonists)
112692-38-3 (Receptor, Serotonin, 5-HT1A)
1RTM4PAL0V (Piperazine)
- Publication Date:
Date Created: 20090630 Date Completed: 20091008 Latest Revision: 20181201
- Publication Date:
20231215
- Accession Number:
10.1016/j.bmc.2009.06.019
- Accession Number:
19559623
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