Synthesis, pharmacological evaluation and molecular modeling studies of triazole containing dopamine D3 receptor ligands
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Acknowledgments
This work was supported by NIH grants DA29840 (R.H.M.), DA23957 and DA13584 (R.R.L.) and Integrated Research Training Program of Excellence in Radiochemistry (60096D).
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2018, Bioorganic and Medicinal Chemistry LettersThe 1,2,3-triazole ring as a bioisostere in medicinal chemistry
2017, Drug Discovery TodayCitation Excerpt :Unfortunately, its triazole derivatives (12) exhibited a reduced activity, probably because of a weak HBD in the triazole [28]. In addition to the aforementioned studies, several authors have reported the synthesis of triazole derivatives of small bioactive molecules, such as N-acetyl β-D-glucopyranosylamine (13) [29–31], ceramides (14) [32–35], dopamine D3 receptor ligands (15) [36–38], N-acyl-homoserine-lactone (16) [39,40], capsaicin (17) [41], hydroxyflutamide (18) [42], biocytin (19) [43], oroidin RA analogs (20) [44], 4-quinolone-3-carboxamides (21) [45], and α-lipoic acid amide derivatives (22) [46,47]. Here, we provide examples in which 1,2,3-triazoles are used as ester isostere to reduce their in vivo susceptibility to enzymatic degradation.
1,4-Disubstituted aromatic piperazines with high 5-HT<inf>2A</inf>/D<inf>2</inf> selectivity: Quantitative structure-selectivity investigations, docking, synthesis and biological evaluation
2015, Bioorganic and Medicinal ChemistryCitation Excerpt :1,2,3-Triazoles share several common physicochemical properties with the amide substructure25 and are easily obtained by click chemistry employing copper(I)-catalyzed 1,3-dipolar cycloadditions,26,27 which allows the investigation of various spacer lengths. The bioisosteric behavior of carboxamides and 1,2,3-triazoles has been successfully exploited for the discovery of dopaminergic D3-receptor ligands.28–30 3D-QSAR models generated from activities of known compounds are attractive alternatives to assist medicinal chemists in rational drug design, for example when crystal structures of protein targets are not available.