Transition-metal-free C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-]pyridines and 2-pyridones from ynones

Herein, a transition metal-free and efficient cascade reaction of ynones with 2-methylbenzimidazoles under mild conditions has been revealed. This cascade reaction involved a Michael addition/intramolecular cycloaddition/dehydration and provided the desired benzo[4,5]imidazo[1,2- a ]pyridines in mod...

Full description

Saved in:
Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2018, Vol.2 (9), p.27-212
Main Authors: Teng, Qing-Hu, Peng, Xiang-Jun, Mo, Zu-Yu, Xu, Yan-Li, Tang, Hai-Tao, Wang, Heng-Shan, Sun, Hong-Bin, Pan, Ying-Ming
Format: Article
Language:English
Subjects:
Apoptosis
Bladder
Calcium (mitochondrial)
Calcium ions
Cancer
Cascade chemical reactions
Caspase
Caspase-3
Cell cycle
Cycle ratio
Cycloaddition
Dehydration
Green chemistry
Liver
Liver cancer
Membrane potential
Metals
Mitochondria
Ovarian cancer
Pyridines
Tumor cell lines
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Herein, a transition metal-free and efficient cascade reaction of ynones with 2-methylbenzimidazoles under mild conditions has been revealed. This cascade reaction involved a Michael addition/intramolecular cycloaddition/dehydration and provided the desired benzo[4,5]imidazo[1,2- a ]pyridines in moderate to good yield. Furthermore, three benzo[4,5]imidazo[1,2- a ]pyridines ( 3d , 3i , and 3q ) exhibited good activities against Hep-G2 (human liver cancer), T-24 (human bladder cancer cell), and SK-OV-3 (human ovarian cancer) cell lines with IC 50 values in the range of 8.05-10.67 μmol L −1 . To investigate the mechanism of the effective inhibition of cell growth, further studies, including cell cycle analysis, apoptosis ratio detection, measurement of Ca 2+ generation, ROS, mitochondrial membrane potential assay, and caspase-3/9 activation, were carried out on compound 3i . We have developed a facile method for the synthesis of benzo[4,5]imidazo[1,2- a ]pyridines and 2-pyridones from readily available ynones and 2-methylbenzimidazoles or acetamides.
ISSN:1463-9262
1463-9270
DOI:10.1039/c8gc00069g