Literature DB >> 25125709

Tetrasubstituted pyrazinones derived from the reaction of praziquantel with N-bromosuccinimide.

Qingjie Zhao1, Chunkai Wang1, Edward L Ezell2, Yuxiang Dong1, Jonathan L Vennerstrom1.   

Abstract

When praziquantel was exposed to N-bromosuccinimide in the presence of ethanol, a tricyclic 3-bromo-1-ethoxy pyrazinone was formed. From this and the analogous 1,3-dibromopyrazinone, a small library of 3-alkylamino-1-ethoxy, 1,3-dialkoxy, 3-alkoxy-1-bromo, and 3-alkylamino-1-bromo substituted pyrazinones were synthesized in high yields.

Entities:  

Keywords:  N-bromosuccinimide; piperazinone; praziquantel; pyrazinone

Year:  2014        PMID： 25125709      PMCID： PMC4128413          DOI： 10.1016/j.tetlet.2014.06.083

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  16 in total

1.  Virtual computational chemistry laboratory--design and description.

Authors:  Igor V Tetko; Johann Gasteiger; Roberto Todeschini; Andrea Mauri; David Livingstone; Peter Ertl; Vladimir A Palyulin; Eugene V Radchenko; Nikolay S Zefirov; Alexander S Makarenko; Vsevolod Yu Tanchuk; Volodymyr V Prokopenko
Journal:  J Comput Aided Mol Des       Date:  2005-06       Impact factor: 3.686

Review 2.  Praziquantel: mechanisms of anti-schistosomal activity.

Authors:  P Andrews
Journal:  Pharmacol Ther       Date:  1985       Impact factor: 12.310

3.  A total synthesis of sporidesmin A.

Authors:  Y Kishi; S Nakatsuka; T Fukuyama; M Havel
Journal:  J Am Chem Soc       Date:  1973-09-19       Impact factor: 15.419

4.  Design, synthesis, and SAR of a novel pyrazinone series with non-nucleoside HIV-1 reverse transcriptase inhibitory activity.

Authors:  Jan Heeres; Marc R de Jonge; Lucien M H Koymans; Frits F D Daeyaert; Maarten Vinkers; Koen J A Van Aken; Eddy Arnold; Kalyan Das; Amuri Kilonda; Georges J Hoornaert; Frans Compernolle; Marek Cegla; Rasha A Azzam; Koen Andries; Marie-Pierre de Béthune; Hilde Azijn; Rudi Pauwels; Paul J Lewi; Paul A J Janssen
Journal:  J Med Chem       Date:  2005-03-24       Impact factor: 7.446

Review 5.  Antischistosomal drugs: past, present ... and future?

Authors:  D Cioli; L Pica-Mattoccia; S Archer
Journal:  Pharmacol Ther       Date:  1995       Impact factor: 12.310

6.  Biotransformation of praziquantel by human cytochrome p450 3A4 (CYP 3A4).

Authors:  Anna Godawska-Matysik; Katarzyna Kieć-Kononowicz
Journal:  Acta Pol Pharm       Date:  2006 Sep-Oct       Impact factor: 0.330

7.  Praziquantel analogs with activity against juvenile Schistosoma mansoni.

Authors:  Yuxiang Dong; Jacques Chollet; Mireille Vargas; Nuha R Mansour; Quentin Bickle; Yazen Alnouti; Jiangeng Huang; Jennifer Keiser; Jonathan L Vennerstrom
Journal:  Bioorg Med Chem Lett       Date:  2010-03-04       Impact factor: 2.823

8.  Uptake and effect of praziquantel and the major human oxidative metabolite, 4-hydroxypraziquantel, by Schistosoma japonicum.

Authors:  S H Xiao; J Q You; H F Guo; B A Catto
Journal:  J Parasitol       Date:  1991-04       Impact factor: 1.276

9.  Praziquantel derivatives I: Modification of the aromatic ring.

Authors:  Fiona Ronketti; A Venkata Ramana; Xia Chao-Ming; Livia Pica-Mattoccia; Donato Cioli; Matthew H Todd
Journal:  Bioorg Med Chem Lett       Date:  2007-05-23       Impact factor: 2.823

Review 10.  The little we know about the pharmacokinetics and pharmacodynamics of praziquantel (racemate and R-enantiomer).

Authors:  Piero Olliaro; Petra Delgado-Romero; Jennifer Keiser
Journal:  J Antimicrob Chemother       Date:  2014-01-02       Impact factor: 5.790
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