O-((Ferrocenyl)(3-fluorophenyl)methyl)hydroxylamine

Angeliki S Foscolos,Aristeidis Chiotellis,Maria Georgiou,Minas S Papadopoulos

doi:10.3390/m1346

Abstract

Based on the diaryl hydroxylamine scaffold, which exhibits the potential to inhibit all three enzymes of the first step of the kynurenine pathway, the main tryptophan degradation pathway in mammals, which is often activated in cancer, we report herein the synthesis of a ferrocenyl analogue as an attempt to improve the scaffold’s pan-inhibitory potency through the isosteric replacement of a phenyl group with the ferrocenyl moiety. The synthetic methodology followed gives access to O-((ferrocenyl)(aryl)methyl)hydroxylamines, a class of compounds not yet reported in the literature.

Highlights

The use of ferrocene building blocks in medicinal chemistry is an intriguing research area
Results and and/or pan-inhibitors of the kynurenineAcademic Editor: Fawaz pathway (KP), we present here the synthesis of the title compound
The synthetic route to ferrocene hydroxylamine 6 is shown in Scheme 1 and involves

Summary

Introduction

The use of ferrocene building blocks in medicinal chemistry is an intriguing research area. Apart from its anticancer, antibacterial, antifungal, and antiparasitic potential [1], Citation: Foscolos, A.S.; Georgiou, the ferrocenyl moiety has been increasingly used in drug design [2]. M.; Papadopoulos, M.S.; Chiotellis, A. bioisosteric replacement of a phenyl ring or heteroaromatic with the ferrocenyl group can. O-((Ferrocenyl)(3lead to compounds with enhanced potency and/or selectivity, compared with the parent, fluorophenyl)methyl)hydroxylamine. Diaryl hydroxylamines with a wide variety of substituted phenyl. Was identified as one of the best analogues but still not with the desired potency. Bioisostericreplacement replacementofofa phenyl a phenyl group with ferrocenyl moiety a known

Bioisosteric group with ferrocenyl moiety on aon known

Synthesis

General

O-((Ferrocenyl)(3-fluorophenyl)methyl)hydroxylamine

Conclusions