Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives
New polysubstituted N-arylpyrazole derivatives were synthesized from N1-arylsydnone with acetylene and boronic acid, including 2-thiophenyl, 3-thiophenyl, 2-benzo[b]thiophenyl, or dibenzothiophenyl-4-boronic acid, via 1,3-dipolar cycloaddition and Suzuki coupling reaction. Based on the growth inhibi...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2019-12-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S187853521400344X |
| _version_ | 1828768531220529152 |
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| author | Naoto Uramaru En-Chiuan Chang Wan-Ping Yen Mou-Yung Yeh Shin-Hun Juang Fung Fuh Wong |
| author_facet | Naoto Uramaru En-Chiuan Chang Wan-Ping Yen Mou-Yung Yeh Shin-Hun Juang Fung Fuh Wong |
| author_sort | Naoto Uramaru |
| collection | DOAJ |
| description | New polysubstituted N-arylpyrazole derivatives were synthesized from N1-arylsydnone with acetylene and boronic acid, including 2-thiophenyl, 3-thiophenyl, 2-benzo[b]thiophenyl, or dibenzothiophenyl-4-boronic acid, via 1,3-dipolar cycloaddition and Suzuki coupling reaction. Based on the growth inhibitory activity results against lung carcinoma (NCI-H226), nasopharyngeal (NPC-TW01), and T-cell leukemia (Jurkat) cancer cells, compounds 5d and 7d with dibenzothiophenyl bioisostere possessed the significant inhibitory activity for NPC-TW01 (32 μM and 16 μM) and NCI-H226 (16 μM and 8.9 μM), respectively. Keywords: Thiophene, Benzothiophene, Pyrazole, Suzuki coupling reaction, Bioactivity study |
| first_indexed | 2024-12-11T13:31:28Z |
| format | Article |
| id | doaj.art-ba4bcb352881465b8962b8a273148a61 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-11T13:31:28Z |
| publishDate | 2019-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-ba4bcb352881465b8962b8a273148a612022-12-22T01:05:15ZengElsevierArabian Journal of Chemistry1878-53522019-12-0112819081917Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivativesNaoto Uramaru0En-Chiuan Chang1Wan-Ping Yen2Mou-Yung Yeh3Shin-Hun Juang4Fung Fuh Wong5Department of Environmental Science, Nihon Pharmaceutical University, 10281, Komuro, Ina-machi, Kitaadachi-gun, Saitama, JapanDepartment of Chemistry, National Cheng Kung University, No. 1, Ta Hsueh Rd., Tainan 70101, Taiwan, ROCSchool of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan, ROCDepartment of Chemistry, National Cheng Kung University, No. 1, Ta Hsueh Rd., Tainan 70101, Taiwan, ROCSchool of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan, ROC; Department of Medical Research, China Medical University Hospital, Taichung, Taiwan; Corresponding authors at: School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan, ROC (F.F. Wong). Tel.: +886 4 2205 3366x5603; fax: +886 4 2207 8083.School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan, ROC; Corresponding authors at: School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan, ROC (F.F. Wong). Tel.: +886 4 2205 3366x5603; fax: +886 4 2207 8083.New polysubstituted N-arylpyrazole derivatives were synthesized from N1-arylsydnone with acetylene and boronic acid, including 2-thiophenyl, 3-thiophenyl, 2-benzo[b]thiophenyl, or dibenzothiophenyl-4-boronic acid, via 1,3-dipolar cycloaddition and Suzuki coupling reaction. Based on the growth inhibitory activity results against lung carcinoma (NCI-H226), nasopharyngeal (NPC-TW01), and T-cell leukemia (Jurkat) cancer cells, compounds 5d and 7d with dibenzothiophenyl bioisostere possessed the significant inhibitory activity for NPC-TW01 (32 μM and 16 μM) and NCI-H226 (16 μM and 8.9 μM), respectively. Keywords: Thiophene, Benzothiophene, Pyrazole, Suzuki coupling reaction, Bioactivity studyhttp://www.sciencedirect.com/science/article/pii/S187853521400344X |
| spellingShingle | Naoto Uramaru En-Chiuan Chang Wan-Ping Yen Mou-Yung Yeh Shin-Hun Juang Fung Fuh Wong Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives Arabian Journal of Chemistry |
| title | Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives |
| title_full | Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives |
| title_fullStr | Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives |
| title_full_unstemmed | Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives |
| title_short | Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives |
| title_sort | synthesis and evaluation of in vitro bioactivity for polysubstituted n arylpyrazole derivatives |
| url | http://www.sciencedirect.com/science/article/pii/S187853521400344X |
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