Synthesis and polymerization of 1-(2-diallylaminoethyl)pyrimidines

Elaridi, Jomana; Ezzeddine, Alaa; Abramian, Lara; Koubeissi, Ali; Vladimirov, Nikolay; Bouhadir, Kamal H.

doi:10.1080/15685551.2018.1448232

Cited by 5 publications

(4 citation statements)

References 43 publications

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“…To obtain the best yield, crude derivative of 2-benzylthiomethyl-1H-benzimidazole (5) react in situ with benzyl chloride or ethyl bromide (6) in the presence of potassium carbonate (K2CO3) in hot dimethylformamide (DMF) to give compound (7). This last step for position-1 modification of the 2benzylthiomethyl-1H-benzimidazole derivative, is performed by introduction of benzyl or alkyl group following a Nalkylation reaction described by Elaridi et al [30] (Figure 1). All compounds obtained were characterized by the 1 H, 13 C NMR spectroscopy and HRMS.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and effect of N-alkylation on antibacterial activity of 2-(Benzylthio) methyl-1H-benzimidazole derivatives

Coulibaly¹,

COULIBALI²,

Bamba³

et al. 2022

GSC Biol. Pharm. Sci.

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In pursuit the development of novel potent and selective antibacterial agents, we synthesized twelve (12) N-alkyl 2-benzylthiomethyl-1H-benzimidazole derivatives and evaluated their antibacterial activities. Their antibacterial profile was determined with minimal inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) against a small set of two (2) strains Escherichia coli (Gram negative) and Staphylococcus aureus (Gram positive). These compounds are produced by the condensation reaction of 2-benzylthiomethyl-1H-benzimidazole (5) with benzyl chloride or bromide (6) in the presence of potassium carbonate (K2CO3). The panel of twelve synthetized compounds (7a-l) were characterized by NMR 1H, 13C spectroscopy, and high-resolution mass spectrometry (HRMS). The results showed that compounds 7a, 7b, 7c, 7d, 7e, 7f, 7h, 7k, and 7l were potent against Escherichia coli and Staphylococcus aureus, with significant MICs values from 140 to 290 µg/mL. On E. coli, five (5) compounds 7b, 7f, 7i, 7k and 7l showed bactericidal effects within common an N-alkylation by R3= phenyl, methyl, and CH2OH on the benzimidazole scaffold and the benzylthiol substituted by R2= Cl or CF3. This is evidence or a probe of these chemical groups implementing the bactericidal activity.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and effect of N-alkylation on antibacterial activity of 2-(Benzylthio) methyl-1H-benzimidazole derivatives

Coulibaly¹,

COULIBALI²,

Bamba³

et al. 2022

GSC Biol. Pharm. Sci.

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“…The molecules were obtained with yields between 51% -94. The method of Nalkylation/arylation consists to treat 2-thiopyrimidine with a base, thus creating an amide ion which will subsequently react with an appropriate carbon chain to lead to N-alkyl derivatives [20,21]. Compounds (8a-k) were obtained using the second method by condensation of 2-alkylsulfanyl-pyrimidine with ethyl or benzyl chloride in the presence of potassium carbonate (K2CO3) under reflux of dimethylformamide (DMF) (Figure 1).…”

Section: Chemistrymentioning

confidence: 99%

Study of the influence of N-alkylation of 2-benzylthiopyrimidines on the growth of two bacteria of medical interest

ACHI¹,

ZON²,

TIMOTOU³

et al. 2022

GSC Adv. Res. Rev.

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The present work highlights the synthesis and effect of introducing substituents on the nitrogen at position -1 of five 2-benzylthiopyrimidine derivatives (6a-e). The compounds (6a-e) were obtained by condensation of 2-thiopyrimidines (4) with benzyl halides in the presence of a base. As for the N-alkylated/arylated-2thiobenzylpyrimidines (8a-k), they were obtained by nucleophilic substitution reaction on nitrogen in basic medium. All the synthesized compounds were characterized by 1H proton, 13C carbon NMR spectroscopic analyses and high resolution mass spectrometry. All compounds were subjected to antibacterial testing on two multidrug resistant strains of Escherichia coli and Staphylococcus aureus. The results revealed that compounds 6a, 6b, 6c, 6d and 6e showed no minimum inhibitory concentration on either E. coli or S. aureus. However, compounds 8b, 8c, 8d and 8f showed a MIC on S. aureus1174. As for the bacterial strain E. coli 1178, only compound 8h showed a minimum inhibitory concentration. N-alkylation/arylation enhanced the antibacterial effect of some 2-benzylthiopyrimidine derivatives.

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“…The pyrimidine‐based monomers 288 afforded copolymer 289 , which may have a multitude of medicinal properties and therapeutic applications (Scheme 50). [139] …”

Section: Synthesis and Applications Of Ph‐responsive Cyclopolymersmentioning

confidence: 99%

“…The pyrimidine-based monomers 288 afforded copolymer 289, which may have a multitude of medicinal properties and therapeutic applications (Scheme 50). [139] Due to their low viscosity, polymers 295 created by the photopolymerization of monomers 292-294 serve as ideal reactive diluents for highly viscous or even solid urethane methacrylates, which are frequently used in the hot lithography industry (Scheme 51). [140] Scheme 44.…”

Section: Other Cyclopolymersmentioning

confidence: 99%

Stimuli‐Responsive Macromolecular Architecture by Butler Cyclopolymerizations: Synthesis and Applications

Ali

Al‐Muallem

Mazumder

2022

The Chemical Record

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This article reviews the synthesis of polyzwitterions (PZs) (poly-carboxybetaines, -phosphonobetaines, and -sulfobetaines) having multiple pH-responsive centers. The synthesis follows the Butler cyclopolymerization protocol involving a multitude of diallylammonium salts and their copolymerization with SO 2 and maleic acid. The PZs have been transformed into cationic-, anionic-polyelectrolytes, and polyampholytes under the influence of pH. Particular attention is given to the application of these polymers as antiscalants, mild steel corrosion inhibitors, components in constructing Aqueous Two-Phase Systems (ATPSs), and membrane modifiers. The ATPSs could be used to separate various biomolecules, including proteins. Many amphiphilic polymers incorporating a few mol % hydrophobic monomers have shown enhanced viscosities and could be suitable for applications in oil fields. The progress of applying Butler cyclopolymerization in reversible addition-fragmentation chain transfer (RAFT) chemistry has been discussed. Future works are expected to focus on RAFT cyclopolymerization to construct block copolymers.

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Synthesis and polymerization of 1-(2-diallylaminoethyl)pyrimidines

Cited by 5 publications

References 43 publications

Synthesis and effect of N-alkylation on antibacterial activity of 2-(Benzylthio) methyl-1H-benzimidazole derivatives

Synthesis and effect of N-alkylation on antibacterial activity of 2-(Benzylthio) methyl-1H-benzimidazole derivatives

Study of the influence of N-alkylation of 2-benzylthiopyrimidines on the growth of two bacteria of medical interest

Stimuli‐Responsive Macromolecular Architecture by Butler Cyclopolymerizations: Synthesis and Applications

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