Synthesis of some benzofuran and furocoumarin derivatives for possible biological activity.
Condensation of 5-formyl-6-methoxy-2,3-diphenylbenzofuran (I) and 6-formyl-5-methoxy-2,3-diphenylbenzofuran (II) with aliphatic or aromatic primary amines led to the formation of the corresponding anils (IIIa-k and IVa-c). The anils (IIIa,f,k or IVa-c) reacted with ethyl cyanoacetate, ethyl acetoacetate, or diethyl malonate to form the respective esters (Va-c or VIa-c). When Va-c or VIa-c were treated with pyridine hydrochloride, demethylation occurred followed by cyclization to form the corresponding furocoumarins (VIIa-c or VIIIa-c). Reduction of the anils using sodium borohydride furnished the corresponding Mannich bases (Xa-d and XI). The antimicrobial activity of compounds IIIi, IVc, Va, VIa, and VIIIa was investigated.
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis; D001419:Bacteria / Q000187:drug effects; D001572:Benzofurans / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005658:Fungi / Q000187:drug effects; D011564:Furocoumarins / Q000138:chemical synthesis* / Q000494:pharmacology; D008352:Mannich Bases / Q000138:chemical synthesis; D015003:Yeasts / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D001572:Benzofurans; D011564:Furocoumarins; D008352:Mannich Bases