Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters was written by Orjales, Aurelio;Mosquera, Ramon;Toledo, Antonio;Pumar, M. Carmen;Garcia, Neftali;Cortizo, Lourdes;Labeaga, Luis;Innerarity, Ana. And the article was included in Journal of Medicinal Chemistry in 2003.Recommanded Product: 2328-12-3 This article mentions the following:
In a wide search program toward new, efficient, and fast-acting antidepressant drugs, series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane) were prepared These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT1A and 5-HT2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidines I (R1 = H, Me, MeCO; R2 = H, 3-F, 4-F, 4-Cl, 4-Me; R3 = H, 2-CN, 4-O2N, 4-MeO, 2-Ph, etc.) showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT1A and 5-HT2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α2 receptor. Several of these enantiomers, (-)-I (R1 = R2 = H; R3 = 2-F), (-)-I (R1 = R2 = H; R3 = 3-F), (-)-I (R1 = H; R2 = 3-F; R3 = 2-F), (+)-I (R1 = H; R2 = R3 = 3-F), displayed a dual binding profile with affinities for SERT and NET with Ki < 25 nM and a NET/SERT ratio <10. (-)-I (R1 = R2 = H; R3 = 3-F) (coded as F-98214-TA for development studies) showed a dual binding profile with very high affinity values for SERT and NET (Ki = 1.9 and 13.5 nM, resp.), and further pharmacol. characterization is in progress for its evaluation as a antidepressant. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Recommanded Product: 2328-12-3).
6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. Tetrahydroisoquinoline motif is often present in natural products with a broad range of biological and pharmacological activities. In particular, 1-benzyl1,2,3,4-tetrahydroisoquinolines are dopamine receptor antagonists. An efficient CuCl2-catalyzed coupling of nonfunctionalized tetrahydroisoquinolines with organozinc reagents under aerobic conditions proceeds in high yields under mild reaction conditions and is broadly applicable to a wide range of substrates. The reaction involves an iminium ion intermediate that is formed via a SET process.Recommanded Product: 2328-12-3
Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem