238422-39-4Relevant academic research and scientific papers
Aza-indolizine with bridgehead nitrogen. Metalation, halogen-metal exchange and directed ortho-lithiation in the imidazo[1,2-a]pyrazine series
Vitse, Olivier,Bompart, Jacques,Subra, Guy,Viols, Henri,Escale, Roger,Chapat, Jean P.,Bonnet, Pierre A.
, p. 6485 - 6496 (1998)
The n-BuLi and lithium 2,2,6,6-tetramethylpiperidine (LTMP) metalation of intidazo[1,2-a]pyrazine heterocycles and subsequent quenching with electrophiles is described. Bromine atoms exhibit different behaviours towards lithiation depending on their positions (3 or 6) on the imidazo[1,2- a]pyrazine heterocycle. Halogen-metal exchange occurs readily with the bromine on position 3. On the contrary, bromine on position 6 only leads to C-5 substituted derivatives further to an ortho-directing effect.
Synthesis and Antibronchospastic Activity of 8-Alkoxy- and 8-(Alkylamino)imidazopyrazines
Bonnet, Pierre A.,Michel, Alain,Laurent, Florence,Sablayrolles, Claire,Rechencq, Eliane,et al.
, p. 3353 - 3358 (2007/10/02)
Theophylline still occupies a dominant place in asthma therapy.Unfortunatly its adverse central nervous system (CNS) stimulant effects can dramatically limit its use, and adjustments in the dosage are often needed.We have synthesized a new series of imidazopyrazine derivatives which are much more potent bronchodilators than theophylline in vivo and do not exhibit the CNS stimulatory profile.In vitro studies on isolated rat uterus and guinea pig trachea confirm the high potentialities of these derivatives. 6-Bromo-8-(methylamino)imidazopyrazine-3-carbonitrile (23) is identified as the most potent compound of the series.As i n the case of theophylline, phosphodiesterase inhibition appears unlikely to be the unique mechanism of the action of this series of heterocycles.
