Synthesis and biological evaluation of novel imidazolidine derivatives as candidates to schistosomicidal agents

Abstract

Introduction: Schistosomiasis is an infectious parasitic disease caused by trematodes of the genus Schistosoma, which threatens at least 258 million people worldwide and its control is dependent on a single drug, praziquantel. The aim of this study was to evaluate the anti-Schistosoma mansoni activity in vitro of novel imidazolidine derivatives. Material and methods: We synthesized two novel imidazolidine derivatives: (LPSF/PTS10) (Z)-1-(2-chloro-6-fluorobenzyl)-4-(4-dimethylaminobenzylidene)-5-thioxoimidazolidin-2-one and (LPSF/PTS23) (Z)-1-(2-chloro-6-fluoro-benzyl)-5-thioxo-4-(2,4,6-trimethoxy-benzylidene)-imidazolidin-2-one. The structures of two compounds were determined by spectroscopic methods. During the biological assays, parameters such as motility, oviposition, mortality and analysis by Scanning Electron Microscopy were performed.Results: LPSF/PTS10 and LPSF/PTS23 were considered to be active in the separation of coupled pairs, mortality and to decrease the motor activity. In addition, LPSF/PTS23 induced ultrastructural alterations in worms, after 24 h of contact, causing extensive erosion over the entire body of the worms.Conclusion: The imidazolidine derivatives containing the trimetoxy and benzylidene halogens showed promising in vitro schistosomicidal activity.

In vivo study of schistosomicidal action of (Z)-1-(2-chloro-6-fluoro-benzyl)-5-thioxo-4-(2,4,6-trimethoxy-benzylidene)-imidazolidin-2-one

“…More recently, evaluation of the schistosomicidal properties of the derivative (Z)-1-(2-chloro-6-fluorobenzyl)-5-thioxo-4-(2,4,6-trimethoxybenzylidene)imidazolidin-2-one or LPSF/PTS23, showed higher activity in vitro against adult male worms, with 100% mortality after 24 hours of contact at all the concentrations tested (Matos-Rocha et al, 2016). This in vitro study of LPSF/PTS23 confirmed the promising in vivo results.…”

“…Based on the promising results of the imidazolidinederived (Z)-1-(2-chloro-6-fluorobenzyl)-5-thioxo-4-(2,4,6-trimethoxybenzylidene)imidazolidin-2-one (LPSF/PTS23) in vitro, this study sought to assess the schistosomicidal potential of LPSF/PTS23 in an experimental model of mansonic schistosomiasis (Matos-Rocha et al, 2016).…”

“…The compound (LPSF/PTS23)-(Z)-1-(2-chloro-6fluorobenzyl)-5-thioxo-4-(2,4,6-trimethoxybenzylidene) imidazolidin-2-one were obtained from Laboratory of Planejamento e Síntese of Fármacos at Universidade Federal de Pernambuco (Brazil) and their identities verified by 1 H nuclear magnetic resonance of hydrogen ( 1 H NMR), infrared (IR) and mass spectroscopy (MS) (Matos-Rocha et al, 2016).…”

Preparation, Characterization, Biological Evaluation and Assess Laser Efficacy for New Derivatives of Imidazolidin-4-one

“…Compound [A1 & A2] showed weak and moderate activity against the bacterial species used. Compounds [A3,A4 & A5] gave strong efficacy and high inhibition, reaching (5) cm at a concentration of (100) mg/ml and reached (4) cm at Concentration (50) mg/ml against all bacterial species used in the study [19][20][21][22][23]. Table (5), and scheme (2-5) demonstrate the effects of the inhibition zone diameter (IZD) in millimeters.…”

New 2‐Oxoimidazolidine Derivatives: Design, Synthesis and Evaluation of Anti‐BK Virus Activities in Vitro

“…Compounds of 4‐oxoimidazolidin‐2‐thione and spiro‐4‐(5‐oxo‐3‐phenyl‐2‐thioxoimidazolidin‐1‐yl)‐2‐(trifluoromethyl)benzonitrile derivatives showed high activity against breast and prostate cancer with IC 50 range of 12.5–13.0 μg/mL and 60–80 n m , respectively. The halogenated trimethoxy and benzylidene imidazolidine derivatives demonstrated in vitro antischistosomiasis activity . Some therapeutically interesting imidazolidine derivatives are presented in Figure .…”