The synthesis and antischistosome properties of 5-(hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3- acetamide (1) are described. The compound was prepared by reduction of the nitrothiazoline (2) with stannous chloride in methanol, and represents the first example of a reduced nitroheterocyclic compound showing potent schistosomicidal properties. The possible relationship of compounds such as 1 to the as yet unidentified reduced active but toxic entities formed in vivo from nitroheterocyclics like metronidazole is discussed.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1007/BF01952092 | DOI Listing |
Molecules
August 2021
Institute of Chemical Technology, Ural Federal University, 19, Mira St, 620002 Ekaterinburg, Russia.
This article presents the results of a study of electrochemical transformations in aqueous and aprotic media of 5-methyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidinide l-arginine monohydrate (, Triazid) obtained by electrochemical methods and ESR spectroscopy. The effect of pH on the current and the reduction potential of in an aqueous Britton-Robinson buffer solution was studied. It was found that 1a is irreversibly reduced in aqueous acidic media on a glassy carbon electrode in one stage with the participation of six electrons and the formation of 5-methyl-6-amino-7-oxo-1,2,4-triazolo[1,5-a]pyrimidin.
View Article and Find Full Text PDFChemosphere
December 2021
Department of Chemical and Environmental Engineering, The University of Arizona, Tucson, AZ, 85721, USA. Electronic address:
As military applications of the insensitive munitions compounds (IMCs) 2,4-dinitroanisole (DNAN) and 3-nitro-1,2,4-triazol-5-one (NTO) increase, there is a growing need to understand their environmental fate and to develop remediation strategies to mitigate their impacts. Iron (II) monosulfide (FeS) minerals are abundant in freshwater and marine sediments, marshes, and hydrothermal environments. This study shows that FeS solids can reduce DNAN and NTO to their corresponding amines under anoxic ambient conditions.
View Article and Find Full Text PDFEnviron Sci Technol
May 2021
Department of Chemical and Environmental Engineering, University of Arizona, Tucson, Arizona 85721-0011, United States.
The nitroheterocyclic 3-nitro-1,2,4-triazol-5-one (NTO) is an ingredient of insensitive explosives increasingly used by the military, becoming an emergent environmental pollutant. Cometabolic biotransformation of NTO occurs in mixed microbial cultures in soils and sludges with excess electron-donating substrates. Herein, we present the unusual energy-yielding metabolic process of NTO respiration, in which the NTO reduction to 3-amino-1,2,4-triazol-5-one (ATO) is linked to the anoxic acetate oxidation to CO by a culture enriched from municipal anaerobic digester sludge.
View Article and Find Full Text PDFAdv Ther (Weinh)
December 2019
Department of Medicine, University of California San Diego, La Jolla, California 92093, USA.
is responsible for the most common non-viral sexually-transmitted disease worldwide. Standard treatment is with oral nitro-heterocyclic compounds, metronidazole or tinidazole, but resistance to these drugs is emerging and adverse effects can be problematic. Topical treatment offers potential benefits for increasing local drug concentrations and efficacy, while reducing systemic drug exposure, but no topical strategies are currently approved for trichomoniasis.
View Article and Find Full Text PDFAntimicrob Agents Chemother
November 2019
Center for Discovery and Innovation in Parasitic Diseases, University of California, San Diego, La Jolla, California, USA
Trichomoniasis is a sexually transmitted disease with hundreds of millions of annual cases worldwide. Approved treatment options are limited to two related nitro-heterocyclic compounds, yet resistance to these drugs is an increasing concern. New antimicrobials against the causative agent, , are urgently needed.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!