Vilsmeier reagent, NaHSe and diclofenac acid chloride: one-pot synthesis of a novel selenoindolinone with potent anticancer activity

Ana Carolina Ruberte; Carlos Aydillo; Arun K Sharma; Carmen Sanmartín; Daniel Plano

doi:10.1039/d0ra07332f

Vilsmeier reagent, NaHSe and diclofenac acid chloride: one-pot synthesis of a novel selenoindolinone with potent anticancer activity

RSC Adv. 2020 Oct 19;10(63):38404-38408. doi: 10.1039/d0ra07332f. eCollection 2020 Oct 15.

Authors

Ana Carolina Ruberte^{1

2}, Carlos Aydillo^{1

2}, Arun K Sharma³, Carmen Sanmartín^{1

2}, Daniel Plano^{1

2}

Affiliations

¹ Universidad de Navarra, Facultad de Farmacia y Nutrición, Departamento de Tecnología y Química Farmacéuticas Irunla-rrea 1 E-31008 Pamplona Spain sanmartin@unav.es +34-948425600 ext. 806388.
² Instituto de Investigación Sanitaria de Navarra (IdiSNA) Irunlarrea, 3 31008 Pamplona Spain.
³ Penn State College of Medicine, Penn State Cancer Institute, CH72, Department of Pharmacology 500 University Drive Hershey Pennsylvania 17033 USA.

Abstract

An effective and straightforward synthesis of 3-seleno functionalized indolinone (5) involving Vilsmeier reagent is presented. Likewise, a procedure to achieve lactamization of diclofenac with excellent yields by using hydrides is also ascertained. Compound 5 exhibited impressive growth inhibition in most of the cell lines in an NCI-60 panel, particularly towards resistant breast cancer cells.