Turkish Journal of Chemistry
Abstract
Four linear nonphenolic diarylheptanoids were synthesized and their antibacterial activities were studied. ($S)$-2-Me-CBS-catalysed reduction of alnustone with BH$_{3}$.SMe$_{2}$ gave ($R)$(-)(4$E$,6$E)$-1,7-diphenylhepta-4,6-dien-3-ol, a natural product. Reduction of alnustone with Na in t-BuOH at -15 $^{\circ}$C under NH$_{3}$ atm gave ($E)$-1,7-diphenylhept-5-en-3-one as a Birch-type reduction product. $t$-BuOK catalysed condensation of benzalacetone with propionyl chloride gave (4$Z$,6$E)$-5-hydroxy-1,7-diphenylhepta-4,6-dien-3-one, a natural product. (1$E$,4$Z$,6$E)$-5-Hydroxy-4-phenethyl-1,7-diphenylhepta-1,4,6-trien-3-one, a curcuminoid, was synthesized starting from pentan-2,4-dione in 3 steps. The synthesized chemical compounds were applied against 2 gram-positive bacteria (Bacillus cereus and Arthrobacter agilis), 4 gram-negative bacteria (Pseudomonas aeruginosa, Xanthomonas campestris, Klebsiella oxytoca and Helicobacter pylori), and 1 yeast (Candida albicans) by the disc diffusion method. All of the synthesized compound exhibited different degrees of antimicrobial activity at concentrations between 20-100 μg/disc against the test organisms.
DOI
10.3906/kim-1911-61
Keywords
Linear diarylheptanoid, curcuminoid, alnustone, natural product, synthesis, antimicrobial activity
First Page
589
Last Page
601
Recommended Citation
DEMİR, Ş. B, SEÇİNTİ, H, ÇELEBİOĞLU, N, ÖZDAL, M, SEZEN, A, GÜLMEZ, Ö, ALGUR, Ö. F, & SEÇEN, H (2020). Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids. Turkish Journal of Chemistry 44 (3): 589-601. https://doi.org/10.3906/kim-1911-61