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Vol. 34 No. 8 (2022): Vol 34 Issue 8, 2022

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Synthesis of Caffeic Acid Derivatives: Identification of (E)-N-(4-Cyanobenzyl)-3-(3,4-dihydroxyphenyl)acrylamide as an Anticancer Agent against Human Cervical Cancer Cells

https://doi.org/10.14233/ajchem.2022.23726
B. Shwetha
Department of Applied Sciences, Visvesvaraya Technological University, Center for Postgraduate Studies, Bengaluru Region, Muddenahalli, Chikkaballapur District-562101, India
M.S. Sudhanva
Adichunchanagiri Institute for Molecular Medicine, Adichunchanagiri University, B.G. Nagara-571448, India
N.R. Thimmegowda
Government S.K.S.J. Technological Institute (Affiliated to Visvesvaraya Technological University), K.R. Circle, Bangalore-560001, India
B.M. Anil Kumar
Adichunchanagiri Institute for Molecular Medicine, Adichunchanagiri University, B.G. Nagara-571448, India
G.S. Jagadeesha
Government S.K.S.J. Technological Institute (Affiliated to Visvesvaraya Technological University), K.R. Circle, Bangalore-560001, India
H. Guddappa
Department of Applied Sciences, Visvesvaraya Technological University, Center for Postgraduate Studies, Bengaluru Region, Muddenahalli, Chikkaballapur District-562101, India
D.S. Prasanna
Department of Applied Sciences, Visvesvaraya Technological University, Center for Postgraduate Studies, Bengaluru Region, Muddenahalli, Chikkaballapur District-562101, India
R. Dinesh
Department of Applied Sciences, Visvesvaraya Technological University, Center for Postgraduate Studies, Bengaluru Region, Muddenahalli, Chikkaballapur District-562101, India
R. Shobith
Adichunchanagiri Institute for Molecular Medicine, Adichunchanagiri University, B.G. Nagara-571448, India
C.S. Anandakumar
Department of Applied Sciences, Visvesvaraya Technological University, Center for Postgraduate Studies, Bengaluru Region, Muddenahalli, Chikkaballapur District-562101, India

Corresponding Author(s) : R. Shobith

shobithrangappa@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 8 (2022): Vol 34 Issue 8, 2022

Abstract

A novel series of natural compound-caffeic acid derivatives were synthesized by coupling with different substituted amines and alkyl halides in an effort to enhance the anticancer activity and explore the structure-activity relationship. The structures of the compounds were determined by 1H NMR and mass spectroscopy analysis. Compounds were evaluated for inhibition against HeLa-cervical cancer cell proliferation and results revealed that compound (E)-N-(4-cyanobenzyl)-3-(3,4-dihydroxyphenyl)acrylamide (SHC5) exhibited potent antiproliferative activity with 5.2 μM concentration and it is further confirmed by Hoechst/PI double staining and Annexin V/PI double staining assay. Further, compound SHC5 was screened against other cancer cell lines namely K562, Jurkat, HCT116 and MiaPaCa2 to test the specificity of the molecule and found to be ineffective.

Keywords

Caffeic acid derivatives Anticancer agents Cervical cancer Natural compound derivatives
Shwetha, B., Sudhanva, M., Thimmegowda, N., Anil Kumar, B., Jagadeesha, G., Guddappa, H., … Anandakumar, C. (2022). Synthesis of Caffeic Acid Derivatives: Identification of (E)-N-(4-Cyanobenzyl)-3-(3,4-dihydroxyphenyl)acrylamide as an Anticancer Agent against Human Cervical Cancer Cells. Asian Journal of Chemistry, 34(8), 2183–2190. https://doi.org/10.14233/ajchem.2022.23726
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