A New Class of Phenazines with Activity against a Chloroquine Resistant Plasmodium falciparum Strain and Antimicrobial Activity

Abstract

New phenazines were synthesized by oxygenation of 1- and 2-naphthol with transition metal peroxo complexes and in situ reaction with 1,2-diamines. The title compounds were evaluated for in vitro antimalarial activity against Plasmodium falciparum and chloroquine-resistant strains. Phenazines 12, 27, and 28 were most prominent in growth inhibition. In vivo protection against cerebral malaria was observed with the phenazines 11, 12, 20, and 27, whereas partial protection was provided by 19.

5-Methyl phenazine-1-carboxylic acid: A novel bioactive metabolite by a rhizosphere soil bacterium that exhibits potent antimicrobial and anticancer activities

“…The ESI-MS and MS/MS data was recorded on ion-trap mass spectrometer (Esquire 3000 plus, Bruker Daltonics, Germany). The 1 H-, 13 C-, 2D 1 H, 1 H-COSY, 1 H-1 H DQF-COSY, 2D 1 H-1 H TOCSY, and 1 H-13 C HSQC-NMR spectra were recorded using a 500 MHz Bruker Avance III spectrometer (Bruker, USA).…”

“…Physical, chemical and biological properties of phenazines often differ on the basis of nature and position of the substituent on the heterocyclic ring [9][10][11]. Phenazine derivatives of natural as well as synthetic origin have attracted considerable attention due to their broad-spectrum antibacterial [10], antifungal [12], antimalarial [13], trypanocidal [14] and antihepatitis C viral replication activities [15]. Moreover, phenazine derivatives have also been reported for antitumor activity in leukemia and solid tumor [16], anti-carcinomatous activity [17] and dual inhibition of topoisomerase I and II enzymes [18,19].…”

Polymerization Inhibitors and Promoters for Unsaturated Polyester Resins; Use of Solid Phase MicroExtraction and Gas Chromatography Coupled to Mass Spectrometry for the Determination of 4-tert-Butyl Catechol and Acetylacetone

“…Methyloxime derivatives produce several abundant fragment ions with low molecular weight that result from simple cleavage or rearrangement followed by fragmentation [29]. We releaved that the o-quinones readily react with MHA to give the corresponding bis-oximes, and the reaction can be pushed to completion if an excess of hydroxylamine is used [30]. The presence of different peaks in the mass spectrum of TBBC-D9 after the derivatization with MHA can be explained taking into account the redox equilibria which quinones and related molecules undergo by simple monoelectronic transfer [31]; indeed the mass peaks that were observed correspond to the TBBC-D9 dioxime, TBBC-D9 semiquinonedihydroxylamine and TBBC-D9 quinonedihydroxylamine which coexist in equilibrium (Figure 3).…”

Phenazine-1-carboxamide (PCN) from Pseudomonas sp. strain PUP6 selectively induced apoptosis in lung (A549) and breast (MDA MB-231) cancer cells by inhibition of antiapoptotic Bcl-2 family proteins

“…[1,2]. The biological potential of phenazines has attracted considerable attention due to their broad-spectrum antibacterial [3], antifungal [4], antimalarial [5], trypanocidal [6], antihepatitis C [7], anticarcinomatous [8] and antitumor activities [9]. Indeed, considering the promising biological properties of natural phenazines, several compounds that contain phenazine as a typical moiety have been synthesised to increase their activity as well as to decrease their toxicity [10,11].…”