Novel 3,3-disubstituted oxindole derivatives. Synthesis and evaluation of the anti-proliferative activity

Michael S Christodoulou; Ferdinando Nicoletti; Katia Mangano; Maria Assunta Chiacchio; Giorgio Facchetti; Isabella Rimoldi; Egle M Beccalli; Sabrina Giofrè

doi:10.1016/j.bmcl.2019.126845

Novel 3,3-disubstituted oxindole derivatives. Synthesis and evaluation of the anti-proliferative activity

Bioorg Med Chem Lett. 2020 Jan 15;30(2):126845. doi: 10.1016/j.bmcl.2019.126845. Epub 2019 Dec 3.

Authors

Michael S Christodoulou¹, Ferdinando Nicoletti², Katia Mangano², Maria Assunta Chiacchio³, Giorgio Facchetti¹, Isabella Rimoldi¹, Egle M Beccalli⁴, Sabrina Giofrè¹

Affiliations

¹ DISFARM, Sezione di Chimica Generale e Organica "A. Marchesini" Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy.
² University of Catania, BIOMETEC, Via Santa Sofia 97, 95123 Catania, Italy.
³ University of Catania, Dipartimento di Scienze del Farmaco, Viale Andrea Doria, 6, 95125 Catania, Italy.
⁴ DISFARM, Sezione di Chimica Generale e Organica "A. Marchesini" Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy. Electronic address: egle.beccalli@unimi.it.

PMID: 31831381
DOI: 10.1016/j.bmcl.2019.126845

Abstract

3,3-Disubstituted oxindole derivatives bearing a nitrogen atom at the C-3 position have been synthesized starting from 3-alkyl oxindole through a metal free pathway. These derivatives have been tested in five human tumor cell lines (PC3, MCF7, SW620, MiaPaca2 and A375) and on primary cells (PBMCs) from healthy donors providing compound 6d showing a strong anticancer effect in all cancer lines on the low micromolar range.

Keywords: 3,3-Disubstituted oxindole; Anti-proliferative activity; Human cancer cell lines; Iminophosphorane; Isocyanate.

Publication types

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

MeSH terms

Cell Proliferation
Humans
Molecular Structure
Oxindoles / chemical synthesis*
Oxindoles / chemistry
Structure-Activity Relationship

Substances

Oxindoles