3‐Arylidene‐N‐hydroxyoxindoles: A New Class of Compounds Endowed with Antitumor Activity

Abstract

A series of compounds containing the N-hydroxyoxindole scaffold were synthesized and evaluated for antitumor activity. The compounds showed potent antiproliferative activity against the wild-type p53 IGROV-1 ovarian carcinoma cell line and considerably lower efficacy against the mutant IGROV-1/Pt1 subline that lacks p53 function. The differential response of ovarian carcinoma cells depending on p53 status was also reflected in the varied susceptibility to apoptosis of the treated cell lines. These results support a role for the p53 transcription factor as a determinant of cytotoxicity. The therapeutic potential of the most promising compound of the series was evaluated in the treatment of an IGROV-1 xenograft growing as ascitic tumor in mice. Using intraperitoneal administration, daily treatment with the compound for four weeks produced a significant delay in the onset of ascites.

Synthesis and biological activity evaluation of 3-(hetero) arylideneindolin-2-ones as potential c-Src inhibitors

“…All the obtained compounds were characterised by NMR analysis, showing the presence of isomeric mixtures (from 9:1 to 7:3 E/Z isomers). The relative ratios of the E and Z stereoisomers within this series ( 32 – 50 ) were assigned based on the chemical shifts of protons at the C2’ and C6’ positions 41 . Previous investigations on 3-arylideneoxindoles have reported the E/Z isomerisation to be solvent-, temperature-, time-, and light-dependent 48–50 .…”

“…Compounds 1 , 2 , 4 38 , 13 , 14 39 , 15 , 16 40 , 7 , 8 , 23 , 24 41 , 9 42 , 10 , 11 43 , 17 44 , 18 45 , 19 45 , 25 46 , 28 47 are part of an in-house library. The synthetic procedures relative to the above-mentioned products have been already described and reported in the cited references.…”

“…1-hydroxy-3–(3-phenoxybenzylidene)indolin-2-one ( 22 ) was prepared from 1-hydroxy-3H-indol-2-one 41 and 3-phenoxybenzaldehyde. Purification by column chromatography (CH 2 Cl 2 /CH 3 OH 97:3) gave the title compound in 85% yield, as a yellow oil.…”

A concise approach to 2-pyrrolin-5-one scaffold construction from α-halohydroxamates and β-keto compounds

“…1) exhibit potential therapeutic activity against Niemann–Pick type C disease (NPC). 2 Dallavalle explored compound III which has antitumor activities, 3 and the general structure IV was found to have good applications in plant protection. 4 Compound V is a potential HIV integrase inhibitor candidate.…”

Natural Hypoxia is Not a Limiting Factor in Evaluating the Novel Arylidene Derivative MLT-401 Against an In Vitro Colorectal Cancer Model

“…To address these physiological concerns, the current study was designed to use the arylidene derivative MLT-401, an indanone compound known for its biologic activity, with special reference to its anti-tumor/cancer efficacy on various cancer models [15, 16]. The selection of MLT-401 was based on its previously reported structural similarity with arylidene indanone molecules having profound anti-tumor activity [17].…”