Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells
In the course of biological properties of quinone derivatives, the N(H)-, S- and S,S-substituted-1,4-naphthoquinones were synthesized by reactions of 2,3-dichloro-1,4-naphthoquinone with different amines (2-morpholinoaniline, tert-butyl 4-aminobenzoate, 4-tert-butylbenzylamine, N-(3-aminopropyl)-2-p...
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| Format: | Article |
| Language: | English |
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De Gruyter
2019-04-01
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| Series: | Open Chemistry |
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| Online Access: | http://www.degruyter.com/view/j/chem.2019.17.issue-1/chem-2019-0030/chem-2019-0030.xml?format=INT |
| _version_ | 1819024324292509696 |
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| author | Kacmaz Aysecik Deniz Nahide Gulsah Aydinli Serdar Goksin Sayil Cigdem Onay-Ucar Evren Mertoglu Elif Arda Nazli |
| author_facet | Kacmaz Aysecik Deniz Nahide Gulsah Aydinli Serdar Goksin Sayil Cigdem Onay-Ucar Evren Mertoglu Elif Arda Nazli |
| author_sort | Kacmaz Aysecik |
| collection | DOAJ |
| description | In the course of biological properties of quinone derivatives, the N(H)-, S- and S,S-substituted-1,4-naphthoquinones were synthesized by reactions of 2,3-dichloro-1,4-naphthoquinone with different amines (2-morpholinoaniline, tert-butyl 4-aminobenzoate, 4-tert-butylbenzylamine, N-(3-aminopropyl)-2-pipecoline, 2-amino-5,6-dimethylbenzothiazole, N,N'-diphenyl-p-phenylenediamine) and thiolat (sodium 2-methyl-2-propanethiolate). All new products were characterized by MS-ESI, UV-Vis, FT-IR, 1H NMR, 13C NMR. The antiproliferative activities of these compounds on human cervical cancer (HeLa) cells were evaluated by MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide) assay. Although all derivatives inhibited cell growth, the most active compound was 2-(tert-butylthio)-3-chloronaphthalene-1,4-dione 5 (IC50=10.16 μM) against the HeLa cells. |
| first_indexed | 2024-12-21T04:52:58Z |
| format | Article |
| id | doaj.art-79cc30a447a8403a94b159b281cd232f |
| institution | Directory Open Access Journal |
| issn | 2391-5420 |
| language | English |
| last_indexed | 2024-12-21T04:52:58Z |
| publishDate | 2019-04-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Open Chemistry |
| spelling | doaj.art-79cc30a447a8403a94b159b281cd232f2022-12-21T19:15:23ZengDe GruyterOpen Chemistry2391-54202019-04-0117133734510.1515/chem-2019-0030chem-2019-0030Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cellsKacmaz Aysecik0Deniz Nahide Gulsah1Aydinli Serdar Goksin2Sayil Cigdem3Onay-Ucar Evren4Mertoglu Elif5Arda Nazli6Division of Organic Chemistry, Department of Chemistry, Faculty of Engineering, Istanbul University-Cerrahpasa, Istanbul34320, TurkeyDivision of Organic Chemistry, Department of Chemistry, Faculty of Engineering, Istanbul University-Cerrahpasa, Istanbul34320, TurkeyDivision of Organic Chemistry, Department of Chemistry, Faculty of Engineering, Istanbul University-Cerrahpasa, Istanbul34320, TurkeyDivision of Organic Chemistry, Department of Chemistry, Faculty of Engineering, Istanbul University-Cerrahpasa, Istanbul34320, TurkeyDepartment of Molecular Biology and Genetics, Faculty of Science, Istanbul University, Istanbul, TurkeyDepartment of Molecular Biology and Genetics, Faculty of Science, Istanbul University, Istanbul, TurkeyDepartment of Molecular Biology and Genetics, Faculty of Science, Istanbul University, Istanbul, TurkeyIn the course of biological properties of quinone derivatives, the N(H)-, S- and S,S-substituted-1,4-naphthoquinones were synthesized by reactions of 2,3-dichloro-1,4-naphthoquinone with different amines (2-morpholinoaniline, tert-butyl 4-aminobenzoate, 4-tert-butylbenzylamine, N-(3-aminopropyl)-2-pipecoline, 2-amino-5,6-dimethylbenzothiazole, N,N'-diphenyl-p-phenylenediamine) and thiolat (sodium 2-methyl-2-propanethiolate). All new products were characterized by MS-ESI, UV-Vis, FT-IR, 1H NMR, 13C NMR. The antiproliferative activities of these compounds on human cervical cancer (HeLa) cells were evaluated by MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide) assay. Although all derivatives inhibited cell growth, the most active compound was 2-(tert-butylthio)-3-chloronaphthalene-1,4-dione 5 (IC50=10.16 μM) against the HeLa cells.http://www.degruyter.com/view/j/chem.2019.17.issue-1/chem-2019-0030/chem-2019-0030.xml?format=INTquinonesaminesthiolsantiproliferative activityhela cell |
| spellingShingle | Kacmaz Aysecik Deniz Nahide Gulsah Aydinli Serdar Goksin Sayil Cigdem Onay-Ucar Evren Mertoglu Elif Arda Nazli Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells Open Chemistry quinones amines thiols antiproliferative activity hela cell |
| title | Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells |
| title_full | Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells |
| title_fullStr | Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells |
| title_full_unstemmed | Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells |
| title_short | Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells |
| title_sort | synthesis and antiproliferative evaluation of some 1 4 naphthoquinone derivatives against human cervical cancer cells |
| topic | quinones amines thiols antiproliferative activity hela cell |
| url | http://www.degruyter.com/view/j/chem.2019.17.issue-1/chem-2019-0030/chem-2019-0030.xml?format=INT |
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