Design, synthesis and antibacterial assessment of novel 4H-chromene analogues

Abstract

The significant medicinal and pharmacological facts about chromenes (benzopyran) nucleus prompted us to focus on constructing unique chromenes with biological value. New chromene derivatives 2–15 were synthesized, and their antibacterial effectiveness was studied. The reaction of the 2-amino-4H-chromene derivative 1 with a variety of reagents such as acetic anhydride, formic acid, chloroacetyl chloride, cyclopentanone, ethyl acetoacetate, diethyl malonate, aldehydes, and isatin produced derivatives 2–13. Compound 1 was also treated with aromatic amines such as p-toluidine and/or benzene-1,4-diamine with formaldehyde, yielding derivatives 14 and 15, respectively; spectral techniques were used to confirm the predicted structures of all compounds. The antibacterial activity of the recently synthesized compounds was assessed against two types of bacteria, Bacillus subtilis and Escherichia coli. There is encouraging antibacterial activity in compounds 5 and 7.

Graphical Abstract

Keywords:

• 1,3-oxazine
• 4-anisaldehyde
• 4H-chromene
• Bacillus subtilis
• chloroacetamide
• Escherichia coli

Disclosure statement

No potential conflict of interest was reported by the author(s).