Synthesis and cytotoxic evaluation of some novel diarylamide possessing quinoxalinedione based on sorafenib
A series of novel sorafenib analogues containing a quinoxalinedione ring and amide linker were synthesized. A total of 9 novel compounds in 6 synthetic steps were synthesized. Briefly, the amino group of p-aminophenol was first protected which then followed by O-arylation with 5-chloro-2-nitroanilin...
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| Format: | Article |
| Language: | English |
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Wolters Kluwer Medknow Publications
2018-01-01
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| Series: | Research in Pharmaceutical Sciences |
| Subjects: | |
| Online Access: | http://www.rpsjournal.net/article.asp?issn=1735-5362;year=2018;volume=13;issue=2;spage=168;epage=176;aulast=Khandan |
| _version_ | 1830132152535089152 |
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| author | Mojtaba Khandan Sedighe Sadeghian Rizi Ghadamali Khodarahmi Farshid Hassanzadeh |
| author_facet | Mojtaba Khandan Sedighe Sadeghian Rizi Ghadamali Khodarahmi Farshid Hassanzadeh |
| author_sort | Mojtaba Khandan |
| collection | DOAJ |
| description | A series of novel sorafenib analogues containing a quinoxalinedione ring and amide linker were synthesized. A total of 9 novel compounds in 6 synthetic steps were synthesized. Briefly, the amino group of p-aminophenol was first protected which then followed by O-arylation with 5-chloro-2-nitroaniline to provide compound d. Reduction of the nitro group of compound d and cyclization of the diamine group of compound e with oxalic acid afforded compound f which on deacetylation yeilded compound g. Then compound g was reacted with different acyl halides to afford the target compounds 1h-1p. Chemical structures of synthesized compounds were confirmed by 1H NMR and FT-IR analysis. All compounds were evaluated at 1, 10, 50 and 100 μM concentrations for their cytotoxicity against HeLa and MCF-7 cancer cell lines. Some of the compounds showed good cytotoxic activity, especially compounds 1i and 1k-1n with the IC50 values of 19, 16, 22, 18, and 16 μM against MCF-7 cell line and 20, 18, 25, 20, and 18 μM against HeLa cell line, respectively. |
| first_indexed | 2024-12-17T06:29:11Z |
| format | Article |
| id | doaj.art-4a93a176926c4954a7c016431af6c542 |
| institution | Directory Open Access Journal |
| issn | 1735-5362 1735-9414 |
| language | English |
| last_indexed | 2024-12-17T06:29:11Z |
| publishDate | 2018-01-01 |
| publisher | Wolters Kluwer Medknow Publications |
| record_format | Article |
| series | Research in Pharmaceutical Sciences |
| spelling | doaj.art-4a93a176926c4954a7c016431af6c5422022-12-21T22:00:11ZengWolters Kluwer Medknow PublicationsResearch in Pharmaceutical Sciences1735-53621735-94142018-01-0113216817610.4103/1735-5362.223802Synthesis and cytotoxic evaluation of some novel diarylamide possessing quinoxalinedione based on sorafenibMojtaba KhandanSedighe Sadeghian RiziGhadamali KhodarahmiFarshid HassanzadehA series of novel sorafenib analogues containing a quinoxalinedione ring and amide linker were synthesized. A total of 9 novel compounds in 6 synthetic steps were synthesized. Briefly, the amino group of p-aminophenol was first protected which then followed by O-arylation with 5-chloro-2-nitroaniline to provide compound d. Reduction of the nitro group of compound d and cyclization of the diamine group of compound e with oxalic acid afforded compound f which on deacetylation yeilded compound g. Then compound g was reacted with different acyl halides to afford the target compounds 1h-1p. Chemical structures of synthesized compounds were confirmed by 1H NMR and FT-IR analysis. All compounds were evaluated at 1, 10, 50 and 100 μM concentrations for their cytotoxicity against HeLa and MCF-7 cancer cell lines. Some of the compounds showed good cytotoxic activity, especially compounds 1i and 1k-1n with the IC50 values of 19, 16, 22, 18, and 16 μM against MCF-7 cell line and 20, 18, 25, 20, and 18 μM against HeLa cell line, respectively.http://www.rpsjournal.net/article.asp?issn=1735-5362;year=2018;volume=13;issue=2;spage=168;epage=176;aulast=Khandancytotoxicity; sorafenib; quinoxalinedione; amide |
| spellingShingle | Mojtaba Khandan Sedighe Sadeghian Rizi Ghadamali Khodarahmi Farshid Hassanzadeh Synthesis and cytotoxic evaluation of some novel diarylamide possessing quinoxalinedione based on sorafenib Research in Pharmaceutical Sciences cytotoxicity; sorafenib; quinoxalinedione; amide |
| title | Synthesis and cytotoxic evaluation of some novel diarylamide possessing quinoxalinedione based on sorafenib |
| title_full | Synthesis and cytotoxic evaluation of some novel diarylamide possessing quinoxalinedione based on sorafenib |
| title_fullStr | Synthesis and cytotoxic evaluation of some novel diarylamide possessing quinoxalinedione based on sorafenib |
| title_full_unstemmed | Synthesis and cytotoxic evaluation of some novel diarylamide possessing quinoxalinedione based on sorafenib |
| title_short | Synthesis and cytotoxic evaluation of some novel diarylamide possessing quinoxalinedione based on sorafenib |
| title_sort | synthesis and cytotoxic evaluation of some novel diarylamide possessing quinoxalinedione based on sorafenib |
| topic | cytotoxicity; sorafenib; quinoxalinedione; amide |
| url | http://www.rpsjournal.net/article.asp?issn=1735-5362;year=2018;volume=13;issue=2;spage=168;epage=176;aulast=Khandan |
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