Synthesis and evaluation of substituted 4-(N-benzylamino)cinnamate esters as potential anti-cancer agents and HIV-1 integrase inhibitors

Faridoon; Adrienne L Edkins; Michelle Isaacs; Dumisani Mnkandhla; Heinrich C Hoppe; Perry T Kaye

doi:10.1016/j.bmcl.2016.05.023

Synthesis and evaluation of substituted 4-(N-benzylamino)cinnamate esters as potential anti-cancer agents and HIV-1 integrase inhibitors

Bioorg Med Chem Lett. 2016 Aug 1;26(15):3810-2. doi: 10.1016/j.bmcl.2016.05.023. Epub 2016 May 9.

Authors

Faridoon¹, Adrienne L Edkins², Michelle Isaacs³, Dumisani Mnkandhla³, Heinrich C Hoppe⁴, Perry T Kaye⁵

Affiliations

¹ Department of Chemistry, Rhodes University, Grahamstown 6140, South Africa.
² Department of Biochemistry and Microbiology, Rhodes University, Grahamstown 6140, South Africa; Biomedical Biotechnology Research Unit (BioBRU), Rhodes University, Grahamstown 6140, South Africa; Centre for Chemico- and Biomedicinal Research, Rhodes University, Grahamstown 6140, South Africa.
³ Centre for Chemico- and Biomedicinal Research, Rhodes University, Grahamstown 6140, South Africa.
⁴ Department of Biochemistry and Microbiology, Rhodes University, Grahamstown 6140, South Africa; Centre for Chemico- and Biomedicinal Research, Rhodes University, Grahamstown 6140, South Africa.
⁵ Department of Chemistry, Rhodes University, Grahamstown 6140, South Africa; Centre for Chemico- and Biomedicinal Research, Rhodes University, Grahamstown 6140, South Africa. Electronic address: [email protected].

PMID: 27317645
DOI: 10.1016/j.bmcl.2016.05.023

Abstract

Encouraging selectivity and low micromolar activity against HeLa cervical carcinoma (IC50⩾3.0μM) and the aggressive MDA-MB-231 triple negative breast carcinoma (IC50⩾9.6μM) cell lines has been exhibited by a number of readily accessible 4-(N-benzylamino)cinnamate esters. The potential of the ligands as HIV-1 integrase inhibitors has also been examined.

Keywords: 4-(N-Benzylamino)cinnamate esters; Anti-cancer agents; HIV-1 integrase inhibitors.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Cinnamates / chemical synthesis
Cinnamates / chemistry
Cinnamates / pharmacology*
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Esters / chemical synthesis
Esters / chemistry
Esters / pharmacology*
HEK293 Cells
HIV Integrase / metabolism*
HIV Integrase Inhibitors / chemical synthesis
HIV Integrase Inhibitors / chemistry
HIV Integrase Inhibitors / pharmacology*
HeLa Cells
Humans
Molecular Structure
Structure-Activity Relationship

Substances

Antineoplastic Agents
Cinnamates
Esters
HIV Integrase Inhibitors
HIV Integrase