213765-61-8Relevant academic research and scientific papers
Anti-Markovnikov Hydroarylation of Unactivated Olefins via Pyridyl Radical Intermediates
Boyington, Allyson J.,Riu, Martin-Louis Y.,Jui, Nathan T.
supporting information, p. 6582 - 6585 (2017/05/29)
The intermolecular alkylation of pyridine units with simple alkenes has been achieved via a photoredox radical mechanism. This process occurs with complete regiocontrol, where single-electron reduction of halogenated pyridines regiospecifically yields the corresponding radicals in a programmed fashion, and radical addition to alkene substrates occurs with exclusive anti-Markovnikov selectivity. This system is mild, tolerant of many functional groups, and effective for the preparation of a wide range of complex alkylpyridines.
Synthesis and evaluation of 3-123I-iodo-5-[2-(S)-3- pyrrolinylmethoxy]-pyridine (niodene) as a potential nicotinic α4β2 receptor imaging agent
Pandey, Suresh K.,Pan, Shawn,Kant, Ritu,Kuruvilla, Sharon A.,Pan, Min-Liang,Mukherjee, Jogeshwar
, p. 7610 - 7614 (2013/02/22)
Nicotinic acetylcholine receptors (nAChRs) are downregulated in disease conditions such as Alzheimer's and substance abuse. Presently, 123I-5-IA-85380 is used in human studies and requires over 6 h of scanning time, thus increases patient disco
2-, 5-, and 6-Halo-3-(2(S)-azetidinylmethoxy)pyridines: Synthesis, affinity for nicotinic acetylcholine receptors, and molecular modeling
Koren, Andrei O.,Horti, Andrew G.,Mukhin, Alexey G.,Gündisch, Daniela,Kimes, Alane S.,Dannals, Robert F.,London, Edythe D.
, p. 3690 - 3698 (2007/10/03)
3-(2(S)-Azetidinylmethoxy)pyridine (A-85380) has been identified recently as a ligad with high affinity for nicotinic acetylcholine receptors (nAChRs). Here we report the synthesis and in vitro nAChR binding of a series of 10 pyridine-modified analogues of A-85380. The novel compounds feature a halogen substituent at position 2, 5, or 6 of the 3-pyridyl fragment. Those with the substituents at position 5 or 6, as well as the 2-fluoro analogue, possess subnanomolar affinity for nAChRs in membranes from rat brain. For these ligands, K(i) values range from 11 to 210 pM, as measured by competition with (±)-[3H]epibatidine. In contrast, 2-chloro, 2-bromo, and 2-iodo analogues exhibit substantially lower affinity. AM1 quantum chemical calculations demonstrate that the bulky substituents at position 2 cause notable changes in the molecular geometry. The high-affinity members of the series and (+)-epibatidine display a tight fit superposition of low-energy stable conformers. The new ligands with high affinity for nAChRs may be of interest as pharmacological probes, potential medications, and candidates for developing radiohalogenated tracers to study nAChRs.
