Research Articles

2019  |  Vol: 5(3)  |  Issue: 3 (May- June)  |  https://doi.org/10.31024/ajpp.2019.5.3.7
Structure-activity relationship of anticancer potential of 4-hydroxycoumarin and its derivatives: A comparative study

Shazia Muzaffar Banday*a, Mehvish Showkatb, Khaliquz Zaman Khana

aDepartment of Chemistry, University of Kashmir, Hazratbal, Srinagar, Jammu & Kashmir, 190006, India

bDepartment of Higher education, Jammu & Kashmir State Government, Jammu & Kashmir, India

*Address for Corresponding author

Shazia Muzaffar Banday

Department of Chemistry, University of Kashmir, Hazratbal, Srinagar, Jammu & Kashmir, 190006, India

Abstract

Objective: In view of high degree of bioactivity shown by 4-hydroxycoumarin and the compounds derived from it, our main aim was to carry out the synthesis of various structurally varied derivatives of 4-hydroxycoumarin and study the effect on their anti-cancer potential. Materials and methods: The reaction of 4-hydroxycoumarin with aldehydes in water was accomplished in an environment friendly approach for the synthesis of biscoumarins. Substituted biscoumarins on treatment with DMSO/acetic anhydride reagent under different conditions lead to various furocoumarins and the related compounds. Synthesis of furocoumarins was also attempted under microwave irradiation conditions starting from 3-bromo-4-hydroxycoumarin. The newly synthesized compounds were evaluated for their antiproliferative activity against human cancer cell line (HeLa) using MTT assay. Results: Synthesis of twenty-two structurally varied derivatives of 4-hydroxycoumarin has been accomplished. All the synthesized compounds were found to have better activity in comparison to the parent 4-hydroxycoumarin moiety. The compounds (5a)(5d)(6a)(6b), (7a)(8a) and (9a) were found to exhibit good activity with an IC50 value below 100μM, the most promising being the compound (6b) with an IC50 value of 55μM. Conclusion: The various products synthesized from 4-hydroxycoumarin were found to have better activity in comparison to the starting compound.

Keywords: 4-hydroxycoumarin, biscoumarin, furocoumarin, anticancer

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