37465-51-3Relevant articles and documents
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)
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.
Synthesis of azocino[5,4-b]indoles via gold-catalyzed intramolecular alkyne hydroarylation
Peshkov, Vsevolod A.,Pereshivko, Olga P.,Der Eycken, Erik V. Van
supporting information, p. 2841 - 2848 (2013/01/15)
An efficient procedure for the synthesis of the azocinoACHTUNGTRENUNG[5,4- b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3-substituted
Meisenheimer rearrangement of azetopyridoindoles. VIII. Synthesis and antiviral activities of 12-carbaeudistomin analogs
Kurihara, Takushi,Sakamoto, Yasuhiko,Kimura, Tetsuya,Ohishi, Hirofumi,Harusawa, Shinya,Yoneda, Ryuji,Suzutani, Tatsuo,Azuma, Masanobu
, p. 900 - 908 (2007/10/03)
Eudistomins, isolated from the colonial tunicate Eudistoma olivaceum, have been a synthetic target due to their strong antiviral activity against Herpes simplesx virus (HSV-1) and activities against certain types of tumors in vivo. In order to examine the
