Cargando…

Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids

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 °C...

Descripción completa

Detalles Bibliográficos
Autores principales: DEMİR, Şemsi Betül, SEÇİNTİ, Hatice, ÇELEBİOĞLU, Neslihan, ÖZDAL, Murat, SEZEN, Alev, GÜLMEZ, Özlem, ALGUR, Ömer Faruk, SEÇEN, Hasan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Scientific and Technological Research Council of Turkey 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7671216/
https://www.ncbi.nlm.nih.gov/pubmed/33488179
http://dx.doi.org/10.3906/kim-1911-61
_version_ 1783610886824394752
author DEMİR, Şemsi Betül
SEÇİNTİ, Hatice
ÇELEBİOĞLU, Neslihan
ÖZDAL, Murat
SEZEN, Alev
GÜLMEZ, Özlem
ALGUR, Ömer Faruk
SEÇEN, Hasan
author_facet DEMİR, Şemsi Betül
SEÇİNTİ, Hatice
ÇELEBİOĞLU, Neslihan
ÖZDAL, Murat
SEZEN, Alev
GÜLMEZ, Özlem
ALGUR, Ömer Faruk
SEÇEN, Hasan
author_sort DEMİR, Şemsi Betül
collection PubMed
description 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 °C under N(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.
format Online
Article
Text
id pubmed-7671216
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Scientific and Technological Research Council of Turkey
record_format MEDLINE/PubMed
spelling pubmed-76712162021-01-22 Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids DEMİR, Şemsi Betül SEÇİNTİ, Hatice ÇELEBİOĞLU, Neslihan ÖZDAL, Murat SEZEN, Alev GÜLMEZ, Özlem ALGUR, Ömer Faruk SEÇEN, Hasan Turk J Chem Article 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 °C under N(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. The Scientific and Technological Research Council of Turkey 2020-06-01 /pmc/articles/PMC7671216/ /pubmed/33488179 http://dx.doi.org/10.3906/kim-1911-61 Text en Copyright © 2020 The Author(s) This article is distributed under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/4.0/ ), which permits unrestricted use and redistribution provided that the original author and source are credited.
spellingShingle Article
DEMİR, Şemsi Betül
SEÇİNTİ, Hatice
ÇELEBİOĞLU, Neslihan
ÖZDAL, Murat
SEZEN, Alev
GÜLMEZ, Özlem
ALGUR, Ömer Faruk
SEÇEN, Hasan
Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids
title Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids
title_full Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids
title_fullStr Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids
title_full_unstemmed Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids
title_short Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids
title_sort syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7671216/
https://www.ncbi.nlm.nih.gov/pubmed/33488179
http://dx.doi.org/10.3906/kim-1911-61
work_keys_str_mv AT demirsemsibetul synthesesandantibacterialactivitiesof4linearnonphenolicdiarylheptanoids
AT secintihatice synthesesandantibacterialactivitiesof4linearnonphenolicdiarylheptanoids
AT celebiogluneslihan synthesesandantibacterialactivitiesof4linearnonphenolicdiarylheptanoids
AT ozdalmurat synthesesandantibacterialactivitiesof4linearnonphenolicdiarylheptanoids
AT sezenalev synthesesandantibacterialactivitiesof4linearnonphenolicdiarylheptanoids
AT gulmezozlem synthesesandantibacterialactivitiesof4linearnonphenolicdiarylheptanoids
AT alguromerfaruk synthesesandantibacterialactivitiesof4linearnonphenolicdiarylheptanoids
AT secenhasan synthesesandantibacterialactivitiesof4linearnonphenolicdiarylheptanoids