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

DOI

10.3906/kim-1911-61

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.

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