192987-39-6Relevant academic research and scientific papers
Asymmetric Construction of Cyclobutanes via Direct Vinylogous Michael Addition/Cyclization of β,γ-Unsaturated Amides
Chen, Yuzhen,Huang, Huicai,Ma, Yan-Yan,Wang, Shuzhong,Wang, Yichen,Zhan, Ruoting,Zhao, Deng-Gao
, p. 7135 - 7140 (2020)
The construction of cyclobutanes has attracted much attention because of its unique four-membered ring skeleton. Herein, we report the highly enantioselective direct vinylogous Michael reaction of β,γ-unsaturated pyrazole amides and nitroolefin using a squaramide catalyst. Cyclobutane derivatives were obtained by subsequent cyclization in good yields (up to 85%) with excellent enantioselectivities (up to 99% ee). Importantly, the large-scale reaction experiment confirmed the reliability of the vinylogous reaction. Furthermore, the synthetic utility of the vinylogous adducts and cyclobutane derivatives has been realized.
Medetomidine analogs as α2-adrenergic ligands. 3. Synthesis and biological evaluation of a new series of medetomidine analogs and their potential binding interactions with α2-adrenoceptors involving a 'methyl pocket'
Zhang, Xiaoyan,De Los Angeles, Joseph E.,He, Mei-Ying,Dalton, James T.,Shams, Gamal,Lei, Longping,Patil, Popat N.,Feller, Dennis R.,Miller, Duane D.,Hsu, Fu-Lian
, p. 3014 - 3024 (2007/10/03)
The synthesis and the biological evaluation of a new series of medetomidine analogs are reported. The substitution pattern at the phenyl ring of the tetralin analogs had a distinct influence on the α2- adrenoceptor binding affinity. 4-Methylindan analog 6 was the most potent α2-adrenoceptor binding ligand among these 4-substituted imidazoles, and its α2-adrenoceptor selectivity was greater than the 5-methyl tetralin analog 4c. Ligand-pharmacophore and receptor modeling were combined to rationalize α2-adrenoceptor binding data of the imidazole analogs in terms of ligand-receptor interactions. The structure-activity relationships that were apparent from this and previous studies were qualitatively rationalized by the binding site models of the α2-adrenoceptor. The benzylic methyl group of medetomidine or the naphthyl analog 2a was superimposable with the α-methyl group of (-)-α-methylnorepinephrine and fit into the proposed 'methyl pocket' of the α2-adrenoceptor defined by the residues Leu110, Leu169, Phe391, and Thr395.
