Synthesis, structural characterization, modal membrane interaction and anti-tumor cell line studies of nitrophenyl ferrocenes

Abstract

A series of nitrophenyl ferrocens (A1-A5) were synthesized and fully characterized in solid state (using CHN analysis, FTIR and single crystal XRD) as well as in solution phase (1 H & 13 C NMR and UV-visible spectroscopy). Micelle interface interactions of these compounds were explored and found to have ability across a micelle membrane interface. Interestingly, these compounds exhibited π-electronic push pull systems and oxidation of ferrocene to ferrocenium on crossing the negative interface of the micelle membrane. Selective compounds were screened for antitumor activity against parental and drug resistant human ovarian tumor models i.e. A2780 and A2780 cisR , A2780 ZD0473R. Screened compounds were found to overcome resistance factor compared to cisplatin.

Synthesis and Antimycobacterial Evaluation of Piperazyl‐alkyl‐Ether Linked 7‐Chloroquinoline‐Chalcone/Ferrocenyl Chalcone Conjugates

“…The replacement of an aryl ring with metal complexes, especially metallocenes has emerged as an important approach in drug discovery, resulting in significant enhancement of activity profiles . Among metallocenes, Ferrocene is considered as very attractive because of its non‐toxoicity, neutral nature and chemical stability .…”

Probing of ferrocenylanilines on model micelle/reverse micelle membrane and their enhanced reactivity for reactive oxidants

“…This is consistent with observations reported previously for the dipicolinate anion in micelles and reverse micelles . The quantification data revealed that pFA, MeFA and mFA have a much greater ability to penetrate into micelles than the corresponding nitro compounds . This pattern of penetration by the ferrocene compounds probably reflect the smaller dipole in the aniline compounds compared to the nitro derivative.…”

“…AOT was further dried under vacuum to remove the minute quantities of water in accordance with literature reports . The reactant nitrophenylferrocenes were prepared and characterized as described in the literature . Doubly distilled and deionized water (17.5 MΩ cm, Barnstead E‐pure) was used.…”

“…Ferrocenylanilines were found to have great importance in medicinal chemistry and as starting materials for many potential anticancer agents . Ferrocene derivatives are well known for their lipophilic and hydrophobic properties, and their medicinal importance is attributed to their lipophilic character . Recent studies showed that ferrocene derivatives are potent in the control of redox reactions in body flux .…”

Confinement Effects on Chemical Equilibria: Pentacyano(Pyrazine)Ferrate(II) Stability Changes within Nanosized Droplets of Water

“…This study imparts insight into how metal complexes behave at interfaces and as solvation is altered at the nanoscale. These insights will be important in the understanding of how molecular species are affected and interact at interfaces or membranes within biological, geological, or industrial systems [ 70 , 71 , 72 , 73 , 74 , 75 , 76 ].…”