Synthesis, antimicrobial evaluation, and molecular docking of some new angular allylbenzochromone derivatives

• Published in: Medicinal chemistry research 2019-10, Vol.28 (10), p.1601-1617
• Main Authors: El-Desoky, El-Sayed I., El-Sawi, Aya A., Abozeid, Mohamed A., Abdelmoteleb, Mohamed, Shaaban, Mona, Keshk, Eman M., Abdel-Rahman, Abdel-Rahman H.
• Format: Article
• Language: English
• Subjects: Activated carbon; Amines; Aminoglycosides; Antiinfectives and antibacterials; Antimicrobial activity; Antimicrobial agents; Antimicrobial resistance; Benzil; Biochemistry; Biomedical and Life Sciences; Biomedicine; Cell Biology; Chemical synthesis; Computer applications; Derivatives; Hydrazine; Hydrazines; Imidazole; Imines; Molecular docking; Nucleophiles; Organic compounds; Original Research; Pharmacology/Toxicology; Quinolines; Software; Sulfonamides; Tetracyclines; Xanthene; β-Lactam antibiotics
• ISSN: 1054-2523; 1554-8120
• DOI: 10.1007/s00044-019-02397-3

Different classes of antimicrobial compounds such as β -lactams, sulfonamides, aminoglycosides, tetracyclines, quinolines and others have been developed during the 20 th century to control the growing antimicrobial resistance. Therefore, there is an urgent need to build up new and effective antimicrobial agents with different working mechanisms to suppress this resistance. Accordingly, the judicious design of antimicrobial organic compounds with antiquorum-sensing activities could be a major solution for this global challenge. Herein, the versatile precursor 6-allyl-3-formyl-4 H -benzo[ h ]chromen-4-one ( 2 ) was used for the synthesis of various isolated and condensed naphthoyl or (chromenyl) nicotinonitriles, azalactone, thiazolidinone, xanthene, indenopyridine, Schiff bases, diazepine, imidazole and triazolopyrimidine derivatives 5 - 21 via its reactions with several active carbon nucleophiles in addition to amines, benzil and hydrazine. Some of the newly synthesized compounds showed moderately and good antimicrobial activities. The compounds 2 and 14 were the best concerning effects. In addition, the antiquorum-sensing activities of the newly prepared compounds were assessed against Chromobacterium violaceum . Specifically, pharmaceutical evaluation, antimicrobial prediction, and molecular docking using computational tools illustrated that the complexes of the latter compounds may show substantial antimicrobial activity in comparison with the other derivatives. New angular allylbenzochromones were synthesized, and their antimicrobial plus antiquorum-sensing activities were evaluated to give 3-formylchrmone 2 and tetracarbonyl 14 as the best antimicrobials. Computational prediction of pharmacokinetics, drug-likeness properties, biological activity, and molecular docking suggested that formyl chromone 2 and tetracarbonyl 14 may be potent antimicrobial drugs.