Literature DB >> 27287623

One-pot three-component Biginelli-type reaction to synthesize 3,4-dihydropyrimidine-2-(1H)-ones catalyzed by Co phthalocyanines: Synthesis, characterization, aggregation behavior and antibacterial activity.

Rawdha Medyouni1, Wissal Elgabsi1, Olfa Naouali2, Antonio Romerosa3, Abdullah Sulaiman Al-Ayed4, Lasaad Baklouti5, Naceur Hamdi6.   

Abstract

The synthesis of a novel phthalonitrile derivative with pyridine-2-thiol and 2,4,6-trimethylphenylamine substituents functionalized groups and its peripherally tetrasubstituted cobalt phthalocyanine and cationic phthalocyanines complexes were reported. The aggregation investigations carried out in different concentrations indicate that Co Phthalocyanines compounds 3,4 do not have any aggregation behavior for the concentration range of 6×10(-4)-14×10(-6)M in DMSO. The ion binding properties of Co Phthalocyanines compounds 3,4 show the formation of stable complex with Co(2+). In addition 3,4-Dihydropyrimidin-2(1H)-one derivatives were synthesized by modified Biginelli cyclocondensation reaction catalyzed by MPc as Lewis base. The structures of the synthesized compounds have been successfully characterized by the spectroscopic methods (IR, (1)H NMR, (13C)NMR, UV-Vis, mass spectrometry, elemental analysis and NMR 2D). The influence of substrate/catalyst ratio, solvent was also investigated to find optimal reaction on this synthesis for getting the highest conversion. Different parameters were examined for finding optimal conditions of catalysis. In addition; the compounds 3-11 were investigated for antimicrobial activity. Most of them exhibited important antimicrobial activity.
Copyright © 2016 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  Aggregation; Characterization; Complexation; Metallophthalocyanine derivatives; Phthalocyanine

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Year:  2016        PMID: 27287623     DOI: 10.1016/j.saa.2016.04.045

Source DB:  PubMed          Journal:  Spectrochim Acta A Mol Biomol Spectrosc        ISSN: 1386-1425            Impact factor:   4.098


  3 in total

Review 1.  Recent developments in the synthesis and applications of dihydropyrimidin-2(1H)-ones and thiones.

Authors:  Behzad Mohammadi; Farahnaz K Behbahani
Journal:  Mol Divers       Date:  2018-01-18       Impact factor: 2.943

2.  An Efficient One-Pot Protocol for the Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones Using Metallophthalocyanines (MPcs) as Potent Heterogeneous Catalysts: Synthesis, Characterization, Aggregation and Antimicrobial Activity.

Authors:  Naceur Hamdi; Rawdha Medyouni; Hallouma Bilel; Lamjed Mansour; Antonio Romerosa
Journal:  Molecules       Date:  2017-04-09       Impact factor: 4.411

3.  Dihydropyrimidinones Against Multiresistant Bacteria.

Authors:  Marisa Castro Jara; Allison Carlos Assunção Silva; Marina Ritter; Adriana Fernandes da Silva; Carolina Lambrecht Gonçalves; Pedro Rassier Dos Santos; Luciano Sisconetto Borja; Cláudio Martin Pereira de Pereira; Patrícia da Silva Nascente
Journal:  Front Microbiol       Date:  2022-03-18       Impact factor: 5.640

  3 in total

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