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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...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Scientific and Technological Research Council of Turkey
2020
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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 |
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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 |
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