Amberlite IR-120H Catalyzed Synthesis of 1,3-Diphenylpyrazolechromenoquinolin-6-one Compounds and Their Biological Evaluation

Author Info

Ahmed Kamal Burri Nagaraju C. Ganesh Kumar Jeshma Kovvuri Jitendra Gour Kishore Mullagiri Narayana Nagesh Sunitha Rani Routhu

Corresponding Author

C. Ganesh Kumar
Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India

A B S T R A C T

A series of 1,3-diphenylpyrazole-chromenoquinolin-6-one compounds were designed and synthesized by using a greener and recyclable heterogeneous Amberlite IR-120H resin as a catalyst, in the presence of ethanol reflux conditions. Interestingly, the catalyst can be recovered after completion of the reaction and can be reused without loss of catalytic property. Therefore, this method provides a green and environmentally benign much improved protocol for the synthesis of 1,3-diphenylpyrazolechromenoquinolin-6-one compounds. The synthesized library of thirty compounds were tested against their cytotoxicity; moreover, the compounds 5s and 5t exhibited potential cytotoxic activity with IC50 values of 1.22 and 1.64 µM, respectively, on MCF-7 cancer cells. The biophysical studies such as UV-visible, fluorescence and circular dichroism studies indicate that these compounds possess good DNA intercalation ability. In addition, these compounds efficiently inhibit topoisomerase I activity. Molecular docking and viscosity studies support that these compounds exhibited intercalative mode of binding with DNA.

Article Info

Article Type

Research Article

Publication history

Received: Sun 01, Mar 2020
Accepted: Mon 13, Apr 2020
Published: Thu 30, Apr 2020

Copyright

© 2023 C. Ganesh Kumar. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Hosting by Science Repository.
DOI: 10.31487/j.AJMC.2020.01.05