An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry

Ibrahim, Tarek S.; Seliem, Israa A.; Panda, Siva S.; Al‐Mahmoudy, Amany M. M.; Abdel‐Samii, Zakaria K.; Alhakamy, Nabil A.; Asfour, Hani Z.; Elagawany, Mohamed

doi:10.3390/molecules25112501

Cited by 6 publications

(3 citation statements)

References 65 publications

(64 reference statements)

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“…All the chemicals were purchased from Sigma-Aldrich (Cairo, Egypt) or Lancaster Synthesis Corporation (London, UK). Intermediates 12 – 15a – j [ 38 , 39 , 40 ] and 17 [ 41 , 42 , 43 ], 18 [ 44 , 45 ] were prepared as previously reported.…”

Section: Methodsmentioning

confidence: 99%

Potent Quinoline-Containing Combretastatin A-4 Analogues: Design, Synthesis, Antiproliferative, and Anti-Tubulin Activity

et al. 2020

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A novel series of quinoline derivatives of combretastatin A-4 incorporating rigid hydrazone and a cyclic oxadiazole linkers were synthesized and have demonstrated potent tubulin polymerization inhibitory properties. Many of these novel derivatives have shown significant antiproliferative activities in the submicromolar range. The most potent compound, 19h, demonstrated superior IC50 values ranging from 0.02 to 0.04 µM against four cancer cell lines while maintaining low cytotoxicity in MCF-10A non-cancer cells, thereby suggesting 19h’s selectivity towards proliferating cancer cells. In addition to tubulin polymerization inhibition, 19h caused cell cycle arrest in MCF-7 cells at the G2/M phase and induced apoptosis. Collectively, these findings indicate that 19h holds potential for further investigation as a potent chemotherapeutic agent targeting tubulin.

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Section: Methodsmentioning

confidence: 99%

Potent Quinoline-Containing Combretastatin A-4 Analogues: Design, Synthesis, Antiproliferative, and Anti-Tubulin Activity

et al. 2020

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“…While acyl-amino acids are environmentally benign regarding application and biological degradation, the conventional chemical synthesis of these compounds via the Schotten-Baumann reaction is not sustainable (Ibrahim et al 2020 ). Chlorinated fatty acids have to be used which are typically produced with toxic phosgene or thionyl chloride.…”

Section: Introductionmentioning

confidence: 99%

Novel recombinant aminoacylase from Paraburkholderia monticola capable of N-acyl-amino acid synthesis

Haeger,

Jolmes,

Oyen

et al. 2024

Appl Microbiol Biotechnol

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N-Acyl-amino acids can act as mild biobased surfactants, which are used, e.g., in baby shampoos. However, their chemical synthesis needs acyl chlorides and does not meet sustainability criteria. Thus, the identification of biocatalysts to develop greener synthesis routes is desirable. We describe a novel aminoacylase from Paraburkholderia monticola DSM 100849 (PmAcy) which was identified, cloned, and evaluated for its N-acyl-amino acid synthesis potential. Soluble protein was obtained by expression in lactose autoinduction medium and co-expression of molecular chaperones GroEL/S. Strep-tag affinity purification enriched the enzyme 16-fold and yielded 15 mg pure enzyme from 100 mL of culture. Biochemical characterization revealed that PmAcy possesses beneficial traits for industrial application like high temperature and pH-stability. A heat activation of PmAcy was observed upon incubation at temperatures up to 80 °C. Hydrolytic activity of PmAcy was detected with several N-acyl-amino acids as substrates and exhibited the highest conversion rate of 773 U/mg with N-lauroyl-L-alanine at 75 °C. The enzyme preferred long-chain acyl-amino-acids and displayed hardly any activity with acetyl-amino acids. PmAcy was also capable of N-acyl-amino acid synthesis with good conversion rates. The best synthesis results were obtained with the cationic L-amino acids L-arginine and L-lysine as well as with L-leucine and L-phenylalanine. Exemplarily, L-phenylalanine was acylated with fatty acids of chain lengths from C8 to C18 with conversion rates of up to 75%. N-lauroyl-L-phenylalanine was purified by precipitation, and the structure of the reaction product was verified by LC–MS and NMR. Key points • A novel aminoacylase from Paraburkholderia monticola was cloned, expressed in E. coli and purified. • The enzyme PmAcy exhibits exceptional temperature and pH stability and a broad substrate spectrum. • Synthesis of acyl amino acids was achieved in good yields.

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“…Besides using of classical acids and bases, several Lewis acid catalysts, solid acid and heteropolyacid catalysts, organocatalysts, ionic liquids and others have been used for the acylation reactions [21]. Amides are commonly produced by N-acylation of amines [22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Magnesium Powder-Catalyzed, Highly Efficient, Solvent-Free Synthesis of Amides through N-Acetylation of Amines and their Antibacterial Activity

Bajracharya,

Shrestha,

Bajracharya

2024

ajc

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Magnesium powder was found to be an efficient catalyst for the acetylation of amines (1) with Ac2O affording corresponding amides (2) in excellent yields (> 99%). This green synthetic protocol has utilized 2.5 mol% of magnesium powder and a stoichiometric amount of Ac2O (1.2 equiv.). Amides 2a-k were synthesized within a short reaction time (2-3 min) at an ambient temperature under solvent free condition. The products were screened against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Staphylococcus epidermidis bacterial strains. N-(2-Hydroxyphenyl)acetamide (2f) was found most active against Gram-positive S. aureus and S. epidermidis indicating its efficacy in treating skin diseases.

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An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry

Cited by 6 publications

References 65 publications

Potent Quinoline-Containing Combretastatin A-4 Analogues: Design, Synthesis, Antiproliferative, and Anti-Tubulin Activity

Potent Quinoline-Containing Combretastatin A-4 Analogues: Design, Synthesis, Antiproliferative, and Anti-Tubulin Activity

Novel recombinant aminoacylase from Paraburkholderia monticola capable of N-acyl-amino acid synthesis

Magnesium Powder-Catalyzed, Highly Efficient, Solvent-Free Synthesis of Amides through N-Acetylation of Amines and their Antibacterial Activity

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