An efficient synthesis of new caffeine-based chalcones, pyrazolines and pyrazolo[3,4-b][1,4]diazepines as potential antimalarial, antitrypanosomal and antileishmanial agents

European Journal of Medicinal Chemistry
Braulio InsuastyJusto Cobo

Abstract

A new series of chalcones 5a-f were synthesized from caffeine-based aldehyde 3 and substituted acetophenones 4a-f. Treatment of compounds 5a-f with hydrazine hydrate led to pyrazolines 6a-f, and their subsequent reaction with acetic anhydride or formic acid afforded the corresponding N-substituted pyrazolines 7a-f and 8a-f respectively. Additionally, the regioselective cyclocondensation reaction of chalcones 5a-f with 4,5-diaminopyrazole 9 afforded the diazepine derivatives 10a-f. Synthesis of the above novel compounds was carried out through a simple procedure involving an easy work-up and mild reaction conditions. In vitro antimalarial activity against Plasmodium falciparum was evaluated for the obtained compounds. Among of them, just pirazoline 6a showed an outstanding growth inhibition percentage 85.2 ± 5.4%, while diazepines 10a-f showed remarkable growth inhibitions in the range of 80.3 ± 13.5 to 94.2 ± 0.2% when were tested at 20 μg/mL. Compounds 5b, 5e, 7c and 7f showed remarkable activities against Leishmania panamensis with growth inhibition of 88.3 ± 1.5, 82.6 ± 2.2, 82.8 ± 1.7 and 87.6 ± 0.5% respectively, at 20 μg/mL. In vitro assays against Trypanozoma cruzi showed that pyrazoline 6d displayed a growth inhibition ...Continue Reading

References

Dec 6, 2011·Bioorganic & Medicinal Chemistry·Gamal El-Din A A Abuo-RahmaHassan H Farag

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Citations

May 7, 2015·Phytotherapy Research : PTR·Yulieth UpeguiFernando Echeverri
May 8, 2016·European Journal of Medicinal Chemistry·Efres Belmonte-RecheJuan Carlos Morales
Jul 30, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alba MontoyaBraulio Insuasty
Jul 21, 2016·Journal of Computer-aided Molecular Design·Rodrigo OchoaCarlos Muskus
Jul 29, 2015·European Journal of Medicinal Chemistry·Juan Carlos CoaSara M Robledo
Mar 23, 2017·European Journal of Medicinal Chemistry·Jonathan Ramírez-PradaBraulio Insuasty
May 28, 2019·Molecular Diversity·Gaurangkumar C BrahmbhattMange Ram Yadav
Jun 17, 2020·Molecular Diversity·Abdolali Alizadeh, Akram Bagherinejad
Aug 3, 2019·Bioorganic Chemistry·Man XuK P Rakesh
Mar 3, 2021·Future Medicinal Chemistry·Dimitris MatiadisGuzmán Alvarez
Apr 6, 2020·Bioorganic & Medicinal Chemistry Letters·Germain HomerinAlina Ghinet
Jul 28, 2018·The Journal of Organic Chemistry·Juan-Carlos CastilloJaime Portilla

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