Design, synthesis of new phenyl acetylene and isoxazole analogues of arjunolic acid as potent tyrosinase and alpha glucosidase inhibitors

Abstract

A series of new phenyl acetylene and isoxazole analogues of arjunolic acid were designed, synthesized and evaluated (3–8) for their tyrosinase and alpha glucosidase inhibitory potential. All the tested analogues exhibited stronger inhibitory activity than the standard drug or parent compound. Of these, compound (7) displayed the most potent tyrosinase inhibitory action with IC₅₀ (14.3 ± 7.6) of about three folds more than the standard drug, kojic acid (41.5 ± 1.0). Further, compound (8) (14.5 ± 0.15) possessed the potent alpha glucosidase inhibitory action with IC₅₀ value comparable to that of standard, acarbose (10.4 ± 0.06). Henceforth, compounds (7) and (8) are promising candidates for further studies.

Graphical Abstract

Keywords:

• Arjunolic acid
• α-glucosidase inihibition
• tyrosinase inhibition

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

We appreciate the encouragement and support of Dr. S. Chandrasekhar, the Director of CSIR-IICT, for provision of facilities. B.E.O acknowledges the support of CSIR-TWAS for postgraduate fellowship award. M.G.P acknowledges grant award from Science and Engineering Research Board, Government of India (EMR/2015/002319). CSIR-IICT Communication No. IICT/Pubs./2021/243.