Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity

Authors

  • Oussama Moussaoui Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, BP 2202 Fez, Morocco
  • El Mestafa El Hadrami Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, BP 2202 Fez, Morocco
  • Ghita Benjalloune Touimi Laboratory of Human Pathology, Biomedicine and Environment, Sidi Mohamed Ben Abdellah University, Faculty of Medicine and Pharmacy, 1893 - KM 2200 Route Sidi Harazem Fez, 30070, Morocco
  • Bahia Bennani Laboratory of Human Pathology, Biomedicine and Environment, Sidi Mohamed Ben Abdellah University, Faculty of Medicine and Pharmacy, 1893 - KM 2200 Route Sidi Harazem Fez, 30070, Morocco
  • Abdeslem Ben Tama Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, BP 2202 Fez, Morocco
  • Said Chakroune Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, BP 2202 Fez, Morocco
  • Abdellatif Boukir Department of Chemistry, Faculty of Sciences and Techniques of Fez, Sidi Mohamed Ben Abdellah University, B.P. 2202, Imouzzer road, Fez, Morocco http://orcid.org/0000-0002-2313-4648

DOI:

https://doi.org/10.13171/mjc941911231077sc

Abstract

Ten new quinoline-carboxamides have been synthesized using the coupling reaction between  2-oxo-1,2-dihydroquinoline-4-carboxylic acid as a substrate and five different amino ester at room temperature with basic media (triethylamine). The products were obtained with a good yield ranging from 60 to 80 % and were structurally characterized by 1H and 13C NMR spectroscopy and mass spectrometry. The antibacterial activities of the synthesized compounds have been evaluated against 9 strains of bacteria and compared to references (erythromycin, ofloxacin, ticarcillin, oxacillin, ampicillin, norfloxacin, ceftazidim, cefotaxim). The results showed that the majority of carboxamides-quinoline ester groups present a larger inhibition diameters than those of the antibiotics references. The highest antibacterial activity in vitro against the Enterococcus feacalis has been revealed for compound 1a (methyl 2-oxo-1.2-dihydroquinoline-4-yl-L-alaninate).

Author Biographies

Oussama Moussaoui, Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, BP 2202 Fez, Morocco

30 000 Fes Morocco

El Mestafa El Hadrami, Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, BP 2202 Fez, Morocco

30 000 Fes Morocco

Ghita Benjalloune Touimi, Laboratory of Human Pathology, Biomedicine and Environment, Sidi Mohamed Ben Abdellah University, Faculty of Medicine and Pharmacy, 1893 - KM 2200 Route Sidi Harazem Fez, 30070, Morocco

30 000 Fes Morocco

Bahia Bennani, Laboratory of Human Pathology, Biomedicine and Environment, Sidi Mohamed Ben Abdellah University, Faculty of Medicine and Pharmacy, 1893 - KM 2200 Route Sidi Harazem Fez, 30070, Morocco

30 000 Fes Morocco

Abdeslem Ben Tama, Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, BP 2202 Fez, Morocco

30 000 Fes Morocco

Said Chakroune, Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, BP 2202 Fez, Morocco

30 000 Fes Morocco

Abdellatif Boukir, Department of Chemistry, Faculty of Sciences and Techniques of Fez, Sidi Mohamed Ben Abdellah University, B.P. 2202, Imouzzer road, Fez, Morocco

30 000 Fes Morocco

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Published

2019-11-23

Issue

Section

Organic Chemistry