93879-05-1Relevant academic research and scientific papers
Ru(II)-catalyzed β-carboline directed C-H arylation and isolation of its cycloruthenated intermediates
Rajkumar, Subramani,Karthik, Shanmugam,Gandhi, Thirumanavelan
, p. 5532 - 5545 (2015)
A Ru(II)-catalyzed C-H arylation approach has been developed utilizing β-carboline alkaloids as the directing group. Selective formations of diarylated products from moderate to excellent yields were accomplished. Broad substrate scope with excellent functional group tolerance for C1-phenyl/thienyl/PAHs-β-carbolines was demonstrated. X-ray crystal structure of cycloruthenated complex 2cr and no arylation reaction with model substrate 13 strongly suggests that N2 is the directing group than N9 in C1-aryl-β-carbolines. Catalytic properties and stability of the cycloruthenated complexes have been explored. Library of biologically relevant new β-carboline derivatives and isolation of its cycloruthenated intermediates are the highlights of this work.
5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines
Toro-Sazo, Miguel,Cassels, Bruce K.,Brea, José,Loza, María I.,Cimadevila, Marta
, (2019/01/25)
The last fifteen years have seen the emergence and overflow into the drug scene of “superpotent” N-benzylated phenethylamines belonging to the “NBOMe” series, accompanied by numerous research articles. Although N-benzyl substitution of 5-methoxytryptamine is known to increase its affinity and potency at 5-HT2 receptors associated with psychedelic activity, N-benzylated tryptamines have been studied much less than their phenethylamine analogs. To further our knowledge of the activity of N-benzyltryptamines, we have synthesized a family of tryptamine derivatives and, for comparison, a few 5-methoxytryptamine analogs with many different substitution patterns on the benzyl moiety, and subjected them to in vitro affinity and functional activity assays vs. the human 5-HT2 receptor subtypes. In the binding (radioligand displacement) studies some of these compounds exhibited only modest selectivity for either 5-HT2A or 5-HT2C receptors suggesting that a few of them, with affinities in the 10–100 nanomolar range for 5-HT2A receptors, might presumably be psychedelic. Unexpectedly, their functional (calcium mobilization) assays reflected very different trends. All of these compounds proved to be 5-HT2C receptor full agonists while most of them showed low efficacy at the 5-HT2A subtype. Furthermore, several showed moderate-to-strong preferences for activation of the 5-HT2C subtype at nanomolar concentrations. Thus, although some N-benzyltryptamines might be abuse-liable, others might represent new leads for the development of therapeutics for weight loss, erectile dysfunction, drug abuse, or schizophrenia.
