Synthesis of Novel 1-(4-Substituted pyridine-3-sulfonyl)-3-phenylureas with Potential Anticancer Activity
A series of novel 4-substituted-N-(phenylcarbamoyl)-3-pyridinesulfonamides 11–27 have been synthesized by the reaction of 4-substituted pyridine-3-sulfonamides 2–10 with the appropriate aryl isocyanates in presence of potassium carbonate. The in vitro anticancer activity of compounds 11, 12, 14–21 a...
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| Format: | Article |
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MDPI AG
2015-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/7/12029 |
| _version_ | 1818126639474671616 |
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| author | Krzysztof Szafrański Jarosław Sławiński |
| author_facet | Krzysztof Szafrański Jarosław Sławiński |
| author_sort | Krzysztof Szafrański |
| collection | DOAJ |
| description | A series of novel 4-substituted-N-(phenylcarbamoyl)-3-pyridinesulfonamides 11–27 have been synthesized by the reaction of 4-substituted pyridine-3-sulfonamides 2–10 with the appropriate aryl isocyanates in presence of potassium carbonate. The in vitro anticancer activity of compounds 11, 12, 14–21 and 24–26 was evaluated at the U.S. National Cancer Institute and in light of the results, some structure-activity relationships were discussed. The most prominent compound, N-[(4-chlorophenyl)carbamoyl]-4-[4-(3,4-dichlorophenyl)piperazin-1-yl]pyridine-3-sulfonamide (21) has exhibited a good activity profile and selectivity toward the subpanels of leukemia, colon cancer and melanoma, with average GI50 values ranging from 13.6 to 14.9 µM. |
| first_indexed | 2024-12-11T07:04:40Z |
| format | Article |
| id | doaj.art-9a6009ab626e41cca94c7f37fb9862fd |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T07:04:40Z |
| publishDate | 2015-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9a6009ab626e41cca94c7f37fb9862fd2022-12-22T01:16:32ZengMDPI AGMolecules1420-30492015-07-01207120291204410.3390/molecules200712029molecules200712029Synthesis of Novel 1-(4-Substituted pyridine-3-sulfonyl)-3-phenylureas with Potential Anticancer ActivityKrzysztof Szafrański0Jarosław Sławiński1Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, PolandDepartment of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, PolandA series of novel 4-substituted-N-(phenylcarbamoyl)-3-pyridinesulfonamides 11–27 have been synthesized by the reaction of 4-substituted pyridine-3-sulfonamides 2–10 with the appropriate aryl isocyanates in presence of potassium carbonate. The in vitro anticancer activity of compounds 11, 12, 14–21 and 24–26 was evaluated at the U.S. National Cancer Institute and in light of the results, some structure-activity relationships were discussed. The most prominent compound, N-[(4-chlorophenyl)carbamoyl]-4-[4-(3,4-dichlorophenyl)piperazin-1-yl]pyridine-3-sulfonamide (21) has exhibited a good activity profile and selectivity toward the subpanels of leukemia, colon cancer and melanoma, with average GI50 values ranging from 13.6 to 14.9 µM.http://www.mdpi.com/1420-3049/20/7/12029sulfonamidespyridine-3-sulfonamidessulfonylureasdiarylsulfonylureasanticancerantitumor activity |
| spellingShingle | Krzysztof Szafrański Jarosław Sławiński Synthesis of Novel 1-(4-Substituted pyridine-3-sulfonyl)-3-phenylureas with Potential Anticancer Activity Molecules sulfonamides pyridine-3-sulfonamides sulfonylureas diarylsulfonylureas anticancer antitumor activity |
| title | Synthesis of Novel 1-(4-Substituted pyridine-3-sulfonyl)-3-phenylureas with Potential Anticancer Activity |
| title_full | Synthesis of Novel 1-(4-Substituted pyridine-3-sulfonyl)-3-phenylureas with Potential Anticancer Activity |
| title_fullStr | Synthesis of Novel 1-(4-Substituted pyridine-3-sulfonyl)-3-phenylureas with Potential Anticancer Activity |
| title_full_unstemmed | Synthesis of Novel 1-(4-Substituted pyridine-3-sulfonyl)-3-phenylureas with Potential Anticancer Activity |
| title_short | Synthesis of Novel 1-(4-Substituted pyridine-3-sulfonyl)-3-phenylureas with Potential Anticancer Activity |
| title_sort | synthesis of novel 1 4 substituted pyridine 3 sulfonyl 3 phenylureas with potential anticancer activity |
| topic | sulfonamides pyridine-3-sulfonamides sulfonylureas diarylsulfonylureas anticancer antitumor activity |
| url | http://www.mdpi.com/1420-3049/20/7/12029 |
| work_keys_str_mv | AT krzysztofszafranski synthesisofnovel14substitutedpyridine3sulfonyl3phenylureaswithpotentialanticanceractivity AT jarosławsławinski synthesisofnovel14substitutedpyridine3sulfonyl3phenylureaswithpotentialanticanceractivity |