17952-87-3Relevant articles and documents
Fischer Reaction with 2-Perfluoroalkylated Cyclic Imines - An Efficient Route to 2-Perfluoroalkyl-Substituted Tryptamines and Their Derivatives and Homologues
Shmatova, Olga I.,Shevchenko, Nikolay E.,Nenajdenko, Valentine G.
, p. 6479 - 6488 (2015/10/19)
The reaction of 2-perfluoroalkyl-substituted cyclic imines with arylhydrazines was investigated. We found that 2-perfluoroalkylated cyclic imines are highly reactive electrophiles that form, through ring opening, the corresponding hydrazones bearing an amine group at the end of the alkyl chain. Subsequent acidic treatment resulted in a Fischer rearrangement. Thus, a new synthesis of 2-perfluoroalkylated tryptamines and their homologues through a Fischer reaction was developed. The possibility of modification of the indole core of the 2-CF3-substituted tryptamine products was demonstrated, and various 2-trifluoromethylated tryptamines substituted at the 5-position were prepared. An efficient method for the synthesis of CF3-substituted tryptamines was developed based on the Fischer reaction of perfluoroalkyl-substituted cyclic imines with arylhydrazines. A 5-bromotryptamine was also transformed into further derivatives.
Syntheses of 7-fluoro- and 6,7-difluoroserotonin and 7-fluoro- and 6,7-difluoromelatonin
Heredia-Moya, Jorge,Hayakawa, Yoshio,Kirk, Kenneth L.
, p. 1256 - 1260 (2008/12/20)
The Abramovitch adaption of the Fischer indole synthesis gave low yields of 7-fluoro-5-methoxytryptamine due in part to decomposition during the required decarboxylation step. Therefore, 7-fluoro- and 6,7-difluoro-5-methoxytryptamines were prepared by rea
N6-Substituted Adenosine Receptor Agonists. Synthesis and Pharmacological Activity as Potent Antinociceptive Agents
Guengoer, Timur,Malabre, Patrice,Teulon, Jean-Marie,Camborde, Francoise,Meignen, Joelle,et al.
, p. 4307 - 4316 (2007/10/02)
Novel N6-(indol-3-yl)alkyl derivatives of adenosine were synthesized.The adenosine receptor affinity and the antinociceptive activity of these compounds were assessed in binding studies and the phenylbenzoquinone-induced writhing test.Most of these analogues exhibited a potent analgesic activity without side effects.Among them, compound 3c (UP 202-32) bound to A1 (Ki = 110 nM) and A2 (Ki = 350 nM) adenosine receptors in a specific manner since it did not interact with many other receptors, especially opioid binding sites.The antinociceptive activity in the phenylbenzoquinone assay (ED50 = 3.3 mg/kg po) was antagonized by 8-cyclopentyltheophylline, suggesting that an adenosinergic mechanism underlies the analgesic activity observed with this compound.The data obtained with these new N6-substituted adenosine receptor agonists emphasize the interest of such compounds in the treatment of pain.
