An improved synthesis of pyrido[2, 3-d]pyrimidin-4(1H)-ones and their antimicrobial activity. Issue 18 (19th April 2018)

• Record Type: Journal Article
• Authors: Fares, Mohamed; Abd El Hadi, Soha R.; Eladwy, Radwa A.; Shoun, Aly A.; Abdel-Aziz, Marwa M.; Eldehna, Wagdy M.; Abdel-Aziz, Hatem A.; Keller, Paul A.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 18(2018)
• Page Start: 3389
• Page End: 3395
• Publication Date: 2018-04-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00627j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The screening of a small chemical library showed 2-thioxodihydropyrido[2, 3- d ]pyrimidine10a had broad spectrum antibacterial activity (MIC 0.49–3.9 μg mL −1 ), and reasonable antifungal activity (MIC 31.25 μg mL −1 ). Abstract : The screening of a small library of diverse chemical structures resulted in the identification of 2-thioxodihydropyrido[2, 3- d ]pyrimidine10a 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 of10a was optimized by varying solvents, catalysts and the use of microwave irradiation with the best conditions using DMF as a solvent, I2 (10 mol%) and a 30 minutes reaction time compared to 15 h for classic conventional heating. The pharmacokinetic properties and calculation of drug likeness of10a suggested good traditional drug-like properties and led to the synthesis of a small library with seven compounds10a and10d–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 compounds10d–i was moderate to strong with MIC values of 1.95–15.63 μg mL −1 .