Synthesis of designed new 1,3,4-oxadiazole functionalized pyrano [2,3-f] chromene derivatives and their antimicrobial activities
Kahdr Alatawi,
Ahmad Fawzi Qarah,
Haifa Alharbi,
Ali Alisaac,
Matokah M. Abualnaja,
Roba M.S. Attar,
Amerah Alsoliemy,
Nashwa M. El-Metwaly
Affiliations
Kahdr Alatawi
Pharmaceuticals Chemistry Department, Faculty of Clinical Pharmacy, Al-Baha University, Al Baha, 65779, Saudi Arabia
Ahmad Fawzi Qarah
Department of Chemistry, College of Science, Taibah University, Madinah, P. O. Box 344, Saudi Arabia
Haifa Alharbi
Department of Chemistry, College of Science, Northern Border University, Saudi Arabia
Ali Alisaac
Department of laboratory Medicine, Faculty of Applied Medical Sciences, Al-Baha University, Saudi Arabia
Matokah M. Abualnaja
Department of Chemistry, Collage of Science, Umm Al-Qura University, Makkah, 24230, Saudi Arabia
Roba M.S. Attar
Department of Biological Sciences/ Microbiology, Faculty of Science, University of Jeddah, P. O. Box 21959, Saudi Arabia
Amerah Alsoliemy
Department of Chemistry, Collage of Science, Umm Al-Qura University, Makkah, 24230, Saudi Arabia
Nashwa M. El-Metwaly
Department of Chemistry, Collage of Science, Umm Al-Qura University, Makkah, 24230, Saudi Arabia; Department of Chemistry, Faculty of Science, Mansoura University, El-Gomhoria Street 35516, Egypt; Corresponding author. Department of Chemistry, Collage of Science, Umm Al-Qura University, Makkah, 24230, Saudi Arabia.
Diethyl 2-(((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methylene)malonate (2) was synthesized from coumarin 1 and diethyl ethoxymethylene malonate in ethanol, followed by cyclization in diphenyl ether to give chromene-9-carboxylate (3). Sugar hydrazones 5a-c were formed by reacting hydrazide 4 with D-galactose, D-mannose, and D-xylose, then acetylated to per-O-acetyl derivatives 6a-c. Heating 5a-c with acetic anhydride at 100 °C gave oxadiazolines 7a-c. Compound 8, obtained by refluxing 4 with carbon disulfide, was alkylated to 9 or reacted to give 10. Further reactions yielded acetoxy derivative 13 and hydroxy derivative 14. Compounds 17a-e and 18a-e were synthesized using thiomorpholinophenyl ureido/thioureido-s-triazine. These compounds were characterized and evaluated for antibacterial activity against Gram (+ve) bacteria (B. subtilis, S. aureus) and Gram (-ve) bacteria (E. coli, P. aeruginosa) in addition to yeast-like fungi (C. albicans). Compounds 11, 13, 15, 16, 17c-e, and 18a-e showed the highest antibacterial activity. Molecular docking was performed to study their binding with transpeptidases.
