139655-01-9Relevant academic research and scientific papers
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.
Ru(II)-catalyzed β-carboline directed C-H arylation and isolation of its cycloruthenated intermediates
Rajkumar, Subramani,Karthik, Shanmugam,Gandhi, Thirumanavelan
, p. 5532 - 5545 (2015/06/16)
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.
Simple and efficient synthesis of tetrahydro-β-carbolines via the Pictet-Spengler reaction in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)
Wang, Li-Na,Shen, Su-Li,Qu, Jin
, p. 30733 - 30741 (2014/08/05)
1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) can act as both the solvent and the catalyst to promote the Pictet-Spengler reactions between tryptamine derivatives and aldehydes or activated ketones. For most substrates, removing the low boiling point HFIP by distillation directly afforded tetrahydro-β-carbolines in high yields.
Highly enantioselective pictet-spengler reaction catalyzed by SPINOL-phosphoric acids
Huang, Dan,Xu, Fangxi,Lin, Xufeng,Wang, Yanguang
supporting information; experimental part, p. 3148 - 3152 (2012/04/17)
Chiral SPINOL-phosphoric acids are highly enantioselective catalysts for the asymmetric Pictet-Spengler reaction of Nb-α-naphthylmethyl tryptamines with a series of aliphatic and aromatic aldehydes, affording optically active tetrahydro-β-carbolines in excellent yields and ee values. The current protocol has been applied in the asymmetric total synthesis of (-)-harmicine. Copyright
Synthesis of tetrahydro-β-carbolines via isomerization of N-allyltryptamines: A metal-catalyzed variation on the Pictet-Spengler theme
Ascic, Erhad,Hansen, Casper L.,Le Quement, Sebastian T.,Nielsen, Thomas E.
supporting information; experimental part, p. 3345 - 3347 (2012/05/04)
An efficient and broadly applicable alternative to the classical Pictet-Spengler synthesis of tetrahydro-β-carbolines is presented. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates which can be trapped by a tethered indole nucleophile. The Royal Society of Chemistry 2012.
Development of the Pictet-Spengler reaction catalyzed by AuCl 3/AgOTf
Youn, So Won
, p. 2521 - 2523 (2007/10/03)
Mild and efficient AuCl3/AgOTf-catalyzed Pictet-Spengler reactions were developed to afford in good yields a variety of tetrahydroisoquinoline and tetrahydro-β-carboline ring systems, which constitute important motifs in biologically active nat
Synthesis of 2-acyltetrahydro-β-carbolines by an intramolecular α- amidoalkylation reaction
Venkov, Atanas P.,Boyadjieva, Atanaska K.
, p. 487 - 494 (2007/10/03)
2-Acyltetrahydro-β-carbolines 7 have been obtained by cyclization of adducts 5 from imines 3 of tryptamine 1 and aldehydes 2 with acyl chlorides 4 as a result of an intramolecular α-amidoalkylation reaction in the presence of bases as N,N-dimethylaniline or Et3N.
Asymmetric Synthesis of Indoloquinolizidin-2-ones Congeners to Yohimbine-Type Alkaloids
Waldmann, Herbert,Braun, Matthias,Weymann, Markus,Gewehr, Markus
, p. 397 - 416 (2007/10/02)
Schiff bases derived from tryptophan methyl ester and tryptamine react with Danishefkys diene in the presence of ZnCl2 to give enaminones which are subsequently transformed into indoloquinolizidin-2-ones by acid-catalyzed cyclization.These tetracyc
