2076-75-7Relevant academic research and scientific papers
Aminomethylation of Imidazoheterocycles with Morpholine
Mondal, Susmita,Samanta, Sadhanendu,Singsardar, Mukta,Hajra, Alakananda
supporting information, p. 3751 - 3754 (2017/07/26)
A hitherto unreported aminomethylation occurs at C-3 of imidazopyridines with morpholine in the presence of (diacetoxyiodo)benzene at ambient temperature in short reaction times. This methodology is also applicable to indolizine, imidazo[2,1-b]thiazole, benzo[d]imidazo[2,1-b]thiazole, and indole. Interestingly, the aminomethylation involving morpholine as a source of methylene group is a new phenomenon. This protocol is of much potential for the synthesis of aminomethylated derivatives under mild reaction conditions.
Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives as selective COX-2 inhibitors
Movahed, Mahsa Azami,Daraei, Bahram,Zarghi, Afshin
, p. 793 - 799 (2016/09/28)
The close structural similarity between cyclooxygenase (COX) isoforms and also the lack of potent selective COX-2 inhibitors with low side effects, stimulate the development of new highly selective COX-2 inhibitors. In this study, a group of imidazo[1,2-a]pyridines was designed, synthesized and investigated to identify potent and selective COX-2 inhibitors. In vitro COX inhibition assay showed that all derivatives were selective COX2 inhibitors with IC50 values in the highly potent 0.07-0.18 μM range and COX-2 selectivity indexes (SI) in 57-217 range. 2-(4-(methylsulfonyl)phenyl)-3-(morpholinomethyl)H-imidazo[1,2-a]pyri-dine (6f) which possessing p-methylsulfonyl phenyl at C-2 of imidazo[1,2-a]pyridine ring, exhibited the highest COX-2 inhibitory selectivity and potency. Molecular modeling and docking studies indicated that synthesized compounds have a binding similar to that of the known inhibitor SC-558 and also methylsulfonyl group can be inserted into the secondary pocket of COX-2. The ability of synthesized compounds for inhibition of platelet aggregation was also determined. Our results demonstrated that 6f was the most potent platelet aggregation inhibitor as well.
