Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 108, 2016, Issue in Progress
Previous Article Next Article

Synthesis and anti-proliferative evaluation of novel 3,4-dihydro-2H-1,3-oxazine derivatives of bakuchiol

Author affiliations

Abstract

A new series of 3,4-dihydro-2H-1,3-oxazine derivatives of bakuchiol 1 was synthesized through the Mannich-type condensation–cyclization reaction of 1 with formaldehyde and appropriate primary amines. On cytotoxicity evaluation against a panel of four human cancer cell lines, most of the derivatives showed a higher cytotoxic profile than the parent molecule. The best results were observed for compound 15 with IC50 values of 2, 2, 2.4 and 3 μM against MIA-Pa-Ca-2, HCT-116, MCF-7 and HL-60 cells, respectively. A mechanistic study of compound 15 revealed that it caused a loss in the mitochondrial membrane potential in a concentration-dependent manner, accompanied by the activation of caspase-9 and -3, which cleave PARP-1. It also activated caspase-8, which is involved in the extrinsic apoptotic pathway. Therefore, we demonstrated that it induces apoptosis via both intrinsic and extrinsic pathways in human pancreatic cancer MIA-Pa-Ca-2 cells.

Graphical abstract: Synthesis and anti-proliferative evaluation of novel 3,4-dihydro-2H-1,3-oxazine derivatives of bakuchiol

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 24 Sep 2016, accepted on 14 Oct 2016 and first published on 14 Oct 2016


Article type: Paper
DOI: 10.1039/C6RA23757F
Citation: RSC Adv., 2016,6, 106150-106159
  •   Request permissions

    Synthesis and anti-proliferative evaluation of novel 3,4-dihydro-2H-1,3-oxazine derivatives of bakuchiol

    N. Gupta, S. Sharma, A. Raina, N. A. Dangroo, S. Bhushan and Payare L. Sangwan, RSC Adv., 2016, 6, 106150
    DOI: 10.1039/C6RA23757F

Search articles by author