Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted
A series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compo...
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| Format: | Article |
| Language: | English |
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Wiley
2019-01-01
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| Series: | Heteroatom Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/1658417 |
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| author | Semih Kurban Nahide Gulsah Deniz Cigdem Sayil Mustafa Ozyurek Kubilay Guclu Maryna Stasevych Viktor Zvarych Olena Komarovska-Porokhnyavet Volodymyr Novikov |
| author_facet | Semih Kurban Nahide Gulsah Deniz Cigdem Sayil Mustafa Ozyurek Kubilay Guclu Maryna Stasevych Viktor Zvarych Olena Komarovska-Porokhnyavet Volodymyr Novikov |
| author_sort | Semih Kurban |
| collection | DOAJ |
| description | A series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tenuis VKM Y-70 and Aspergillus niger F-1119 fungi in comparison with controls was identified. 2-Chloro-3-((2-(piperidin-1-yl)ethyl)amino)naphthalene-1,4-dione 3g and 2,5-dichloro-3-ethoxy-6-((2,4,6-trifluorophenyl)amino)cyclohexa-2,5-diene-1,4-dione 17 were the most potent, with a minimum inhibitory concentration value of 15.6 μg/mL against test-culture M. luteum and S. aureus, respectively. Furthermore, in this work, a catalase activity of benzo- and naphthoquinone derivatives was examined for the first time. The catalase activity of benzo- and naphthoquinone derivatives was determined, showing that compound 3g had significant inhibition activity for catalase enzyme. |
| format | Article |
| id | doaj-art-d02e5e9e329f4595a8517d746d8be848 |
| institution | OA Journals |
| issn | 1042-7163 1098-1071 |
| language | English |
| publishDate | 2019-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Heteroatom Chemistry |
| spelling | doaj-art-d02e5e9e329f4595a8517d746d8be8482025-08-20T02:20:03ZengWileyHeteroatom Chemistry1042-71631098-10712019-01-01201910.1155/2019/16584171658417Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-SubstitutedSemih Kurban0Nahide Gulsah Deniz1Cigdem Sayil2Mustafa Ozyurek3Kubilay Guclu4Maryna Stasevych5Viktor Zvarych6Olena Komarovska-Porokhnyavet7Volodymyr Novikov8Division of Organic Chemistry, Department of Chemistry, Engineering Faculty, Istanbul University-Cerrahpasa, Istanbul, TurkeyDivision of Organic Chemistry, Department of Chemistry, Engineering Faculty, Istanbul University-Cerrahpasa, Istanbul, TurkeyDivision of Organic Chemistry, Department of Chemistry, Engineering Faculty, Istanbul University-Cerrahpasa, Istanbul, TurkeyDivision of Analytical Chemistry, Department of Chemistry, Engineering Faculty, Istanbul University-Cerrahpasa, Istanbul, TurkeyFaculty of Arts and Sciences, Department of Chemistry, Aydın Adnan Menderes University, Aydın, TurkeyDepartment of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Lviv, UkraineDepartment of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Lviv, UkraineDepartment of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Lviv, UkraineDepartment of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Lviv, UkraineA series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tenuis VKM Y-70 and Aspergillus niger F-1119 fungi in comparison with controls was identified. 2-Chloro-3-((2-(piperidin-1-yl)ethyl)amino)naphthalene-1,4-dione 3g and 2,5-dichloro-3-ethoxy-6-((2,4,6-trifluorophenyl)amino)cyclohexa-2,5-diene-1,4-dione 17 were the most potent, with a minimum inhibitory concentration value of 15.6 μg/mL against test-culture M. luteum and S. aureus, respectively. Furthermore, in this work, a catalase activity of benzo- and naphthoquinone derivatives was examined for the first time. The catalase activity of benzo- and naphthoquinone derivatives was determined, showing that compound 3g had significant inhibition activity for catalase enzyme.http://dx.doi.org/10.1155/2019/1658417 |
| spellingShingle | Semih Kurban Nahide Gulsah Deniz Cigdem Sayil Mustafa Ozyurek Kubilay Guclu Maryna Stasevych Viktor Zvarych Olena Komarovska-Porokhnyavet Volodymyr Novikov Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted Heteroatom Chemistry |
| title | Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted |
| title_full | Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted |
| title_fullStr | Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted |
| title_full_unstemmed | Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted |
| title_short | Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted |
| title_sort | synthesis antimicrobial properties and inhibition of catalase activity of 1 4 naphtho and benzoquinone derivatives containing n s o substituted |
| url | http://dx.doi.org/10.1155/2019/1658417 |
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