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An improved synthesis of pyrido[2,3-: d] pyrimidin-4(1 H)-ones and their antimicrobial activity

Journal Article


Abstract


  • The screening of a small library of diverse chemical structures resulted in the identification of 2-thioxodihydropyrido[2,3-d]pyrimidine 10a as having broad spectrum antibacterial activity (MIC 0.49-3.9 μg mL -1 ), and reasonable antifungal activity (MIC 31.25 μg mL -1 ). An expeditious synthesis of 10a was optimized by varying solvents, catalysts and the use of microwave irradiation with the best conditions using DMF as a solvent, I 2 (10 mol%) and a 30 minutes reaction time compared to 15 h for classic conventional heating. The pharmacokinetic properties and calculation of drug likeness of 10a suggested good traditional drug-like properties and led to the synthesis of a small library with seven compounds 10a and 10d-i showing broad antimicrobial activity (MIC = 0.49-7.81 μg mL -1 ) and selectivity indices of more than 5.6 against the normal colon cell line (CCD-33Co). The antifungal activity of compounds 10d-i was moderate to strong with MIC values of 1.95-15.63 μg mL -1 .

Authors


  •   Fares, Mohamed (external author)
  •   Abd El Hadi, Soha (external author)
  •   Eladwy, Radwa A. (external author)
  •   Shoun, Aly (external author)
  •   Abdel-Aziz, Marwa (external author)
  •   Eldehna, Wagdy M. (external author)
  •   Abdel-Aziz, Hatem A. (external author)
  •   Keller, Paul A.

Publication Date


  • 2018

Citation


  • Fares, M., Abd El Hadi, S. R., Eladwy, R. A., Shoun, A. A., Abdel-Aziz, M. M., Eldehna, W. M., Abdel-Aziz, H. A. & Keller, P. A. (2018). An improved synthesis of pyrido[2,3-: d] pyrimidin-4(1 H)-ones and their antimicrobial activity. Organic and Biomolecular Chemistry, 16 (18), 3389-3395.

Scopus Eid


  • 2-s2.0-85046900876

Number Of Pages


  • 6

Start Page


  • 3389

End Page


  • 3395

Volume


  • 16

Issue


  • 18

Place Of Publication


  • United Kingdom

Abstract


  • The screening of a small library of diverse chemical structures resulted in the identification of 2-thioxodihydropyrido[2,3-d]pyrimidine 10a as having broad spectrum antibacterial activity (MIC 0.49-3.9 μg mL -1 ), and reasonable antifungal activity (MIC 31.25 μg mL -1 ). An expeditious synthesis of 10a was optimized by varying solvents, catalysts and the use of microwave irradiation with the best conditions using DMF as a solvent, I 2 (10 mol%) and a 30 minutes reaction time compared to 15 h for classic conventional heating. The pharmacokinetic properties and calculation of drug likeness of 10a suggested good traditional drug-like properties and led to the synthesis of a small library with seven compounds 10a and 10d-i showing broad antimicrobial activity (MIC = 0.49-7.81 μg mL -1 ) and selectivity indices of more than 5.6 against the normal colon cell line (CCD-33Co). The antifungal activity of compounds 10d-i was moderate to strong with MIC values of 1.95-15.63 μg mL -1 .

Authors


  •   Fares, Mohamed (external author)
  •   Abd El Hadi, Soha (external author)
  •   Eladwy, Radwa A. (external author)
  •   Shoun, Aly (external author)
  •   Abdel-Aziz, Marwa (external author)
  •   Eldehna, Wagdy M. (external author)
  •   Abdel-Aziz, Hatem A. (external author)
  •   Keller, Paul A.

Publication Date


  • 2018

Citation


  • Fares, M., Abd El Hadi, S. R., Eladwy, R. A., Shoun, A. A., Abdel-Aziz, M. M., Eldehna, W. M., Abdel-Aziz, H. A. & Keller, P. A. (2018). An improved synthesis of pyrido[2,3-: d] pyrimidin-4(1 H)-ones and their antimicrobial activity. Organic and Biomolecular Chemistry, 16 (18), 3389-3395.

Scopus Eid


  • 2-s2.0-85046900876

Number Of Pages


  • 6

Start Page


  • 3389

End Page


  • 3395

Volume


  • 16

Issue


  • 18

Place Of Publication


  • United Kingdom