Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids

Authors

ŞEMSİ BETÜL DEMİR
HATİCE SEÇİNTİ
NESLİHAN ÇELEBİOĞLU
MURAT ÖZDAL
ALEV SEZEN
ÖZLEM GÜLMEZ
ÖMER FARUK ALGUR
HASAN SEÇEN

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, ŞEMSİ BETÜL; SEÇİNTİ, HATİCE; ÇELEBİOĞLU, NESLİHAN; ÖZDAL, MURAT; SEZEN, ALEV; GÜLMEZ, ÖZLEM; ALGUR, ÖMER FARUK; and SEÇEN, HASAN (2020) "Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids," Turkish Journal of Chemistry: Vol. 44: No. 3, Article 4. https://doi.org/10.3906/kim-1911-61
Available at: https://journals.tubitak.gov.tr/chem/vol44/iss3/4