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Ultrasound-Assisted Synthesis, Antifungal Activity against Fusarium oxysporum, and Three-Dimensional Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from 2-Amino Acids
[Image: see text] A high-yielding, green, and fast synthesis of alkyl 2-substituted {[(alkylsulfanyl)carbonothioyl]amino}acetate-type compounds is described. The one-pot, three-component condensation of alkyl 2-aminoesters, carbon disulfide, and electron-deficient olefins was the key reaction to be...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714526/ https://www.ncbi.nlm.nih.gov/pubmed/31497688 http://dx.doi.org/10.1021/acsomega.9b01098 |
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author | Quiroga, Diego Becerra, Lili Dahiana Coy-Barrera, Ericsson |
author_facet | Quiroga, Diego Becerra, Lili Dahiana Coy-Barrera, Ericsson |
author_sort | Quiroga, Diego |
collection | PubMed |
description | [Image: see text] A high-yielding, green, and fast synthesis of alkyl 2-substituted {[(alkylsulfanyl)carbonothioyl]amino}acetate-type compounds is described. The one-pot, three-component condensation of alkyl 2-aminoesters, carbon disulfide, and electron-deficient olefins was the key reaction to be developed. The products were obtained easily and efficiently, with good overall yields after two steps (79–91%), employing short reaction times, without the use of a catalyst, and ultrasonic irradiation in water. This procedure was exploited to produce antifungals against the phytopathogenic fungus Fusarium oxysporum. Some synthesized compounds exhibited good performance as mycelial growth inhibitors (IC(50) < 80 μM). Structural and antifungal datasets were integrated to explore the comprehensive three-dimensional quantitative structure–activity relationship (3D-QSAR) using comparative molecular field analysis (CoMFA) and explain the observed activity. This integration resulted in an excellent CoMFA model (r(2) = 0.812; q(2) = 0.771) after substructure-based alignment. According to this model, synthesized compounds possessing steric bulky electron-withdrawing groups in the dithiocarbamate moiety can be considered as promising F. oxysporum inhibitors. |
format | Online Article Text |
id | pubmed-6714526 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-67145262019-09-06 Ultrasound-Assisted Synthesis, Antifungal Activity against Fusarium oxysporum, and Three-Dimensional Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from 2-Amino Acids Quiroga, Diego Becerra, Lili Dahiana Coy-Barrera, Ericsson ACS Omega [Image: see text] A high-yielding, green, and fast synthesis of alkyl 2-substituted {[(alkylsulfanyl)carbonothioyl]amino}acetate-type compounds is described. The one-pot, three-component condensation of alkyl 2-aminoesters, carbon disulfide, and electron-deficient olefins was the key reaction to be developed. The products were obtained easily and efficiently, with good overall yields after two steps (79–91%), employing short reaction times, without the use of a catalyst, and ultrasonic irradiation in water. This procedure was exploited to produce antifungals against the phytopathogenic fungus Fusarium oxysporum. Some synthesized compounds exhibited good performance as mycelial growth inhibitors (IC(50) < 80 μM). Structural and antifungal datasets were integrated to explore the comprehensive three-dimensional quantitative structure–activity relationship (3D-QSAR) using comparative molecular field analysis (CoMFA) and explain the observed activity. This integration resulted in an excellent CoMFA model (r(2) = 0.812; q(2) = 0.771) after substructure-based alignment. According to this model, synthesized compounds possessing steric bulky electron-withdrawing groups in the dithiocarbamate moiety can be considered as promising F. oxysporum inhibitors. American Chemical Society 2019-08-12 /pmc/articles/PMC6714526/ /pubmed/31497688 http://dx.doi.org/10.1021/acsomega.9b01098 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Quiroga, Diego Becerra, Lili Dahiana Coy-Barrera, Ericsson Ultrasound-Assisted Synthesis, Antifungal Activity against Fusarium oxysporum, and Three-Dimensional Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from 2-Amino Acids |
title | Ultrasound-Assisted Synthesis, Antifungal Activity
against Fusarium oxysporum, and Three-Dimensional
Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from
2-Amino Acids |
title_full | Ultrasound-Assisted Synthesis, Antifungal Activity
against Fusarium oxysporum, and Three-Dimensional
Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from
2-Amino Acids |
title_fullStr | Ultrasound-Assisted Synthesis, Antifungal Activity
against Fusarium oxysporum, and Three-Dimensional
Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from
2-Amino Acids |
title_full_unstemmed | Ultrasound-Assisted Synthesis, Antifungal Activity
against Fusarium oxysporum, and Three-Dimensional
Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from
2-Amino Acids |
title_short | Ultrasound-Assisted Synthesis, Antifungal Activity
against Fusarium oxysporum, and Three-Dimensional
Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from
2-Amino Acids |
title_sort | ultrasound-assisted synthesis, antifungal activity
against fusarium oxysporum, and three-dimensional
quantitative structure–activity relationship of n,s-dialkyl dithiocarbamates derived from
2-amino acids |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714526/ https://www.ncbi.nlm.nih.gov/pubmed/31497688 http://dx.doi.org/10.1021/acsomega.9b01098 |
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