Synthesis of some bergapten and ammajin derivatives with potential antibacterial activity.
The reaction of bergapten and ammajin with chlorosulfonic acid i shown to give the sulfonyl chlorides 1 and 11 which react with aliphatic, aromatic, and heterocyclic amines to give the corresponding sulfonamides. Phenols also react with 1 and 11 to give the sulfonate esters 5 and 15. Interaction of bergapten with phosphorous(V)sulfide gave the thione 7 which on reaction with amines gave 9. The antibacterial activity of the products is reported.
D000078223:5-Methoxypsoralen; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D011564:Furocoumarins / Q000138:chemical synthesis* / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008730:Methoxsalen / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D008826:Microbial Sensitivity Tests
D000900:Anti-Bacterial Agents; D011564:Furocoumarins; D000078223:5-Methoxypsoralen; D008730:Methoxsalen