Synthesis and antimicrobial activity of some novel derivatives of benzofuran: part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives.
The reaction of salicylaldehyde with 1-chloro-3-mesitylacetone (2) and potassium carbonate was used to prepare 1-(1-benzofuran-2-yl)-2-mesitylethanone (4) for the starting reagent purposes. 1-(1-Benzofuran-2-yl)-2-mesitylethanoneoxime (5) was synthesized by the reaction of the compound (4) with hydroxylamine. New derivative of 1-(1-benzofuran-2-yl)-2-mesitylethanoneoxime (5) as 1-(1-benzofuran-2-yl)-2-mesitylethanonesemicarbazone (7) was obtained in very high yields. Alkyl substituted N-oxime ethers (8a-d) were obtained by the reaction compound 5 and various halogen contained compounds. The compounds 9a-d were synthesized by the reaction of the compound (5) and four different acyl chlorides. Some of the synthesized compounds were tested for antimicrobial activity against Staphylococcus aureus ATCC 6538, Escherichia coli ATCC 25922 and Candida albicans ATCC 10231. Among the synthesized compounds (E)-1-(1-benzofuran-2-yl)-2-mesitylethanone-O-benzoyloxime (9b) was found the most active derivative against S. aureus ATCC 6538 and E. coli ATCC 25922. The other compounds exhibited moderate activity against the other test microorganisms.
Kirilmis
Cumhur
C
Firat University, Faculty of Science and Arts, Department of Chemistry, 23169 Elazig, Turkey. ckirilmis@firat.edu.tr
Ahmedzade
Misir
M
Servi
Süleyman
S
Koca
Murat
M
Kizirgil
Ahmet
A
Kazaz
Cavit
C
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D017550:Spectroscopy, Fourier Transform Infrared; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001572:Benzofurans