Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives

Naoto Uramaru; En-Chiuan Chang; Wan-Ping Yen; Mou-Yung Yeh; Shin-Hun Juang; Fung Fuh Wong

Arabian Journal of Chemistry (Dec 2019)

Synthesis and evaluation of in vitro bioactivity for polysubstituted N-arylpyrazole derivatives

Naoto Uramaru,
En-Chiuan Chang,
Wan-Ping Yen,
Mou-Yung Yeh,
Shin-Hun Juang,
Fung Fuh Wong

Affiliations

Naoto Uramaru: Department of Environmental Science, Nihon Pharmaceutical University, 10281, Komuro, Ina-machi, Kitaadachi-gun, Saitama, Japan
En-Chiuan Chang: Department of Chemistry, National Cheng Kung University, No. 1, Ta Hsueh Rd., Tainan 70101, Taiwan, ROC
Wan-Ping Yen: School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan, ROC
Mou-Yung Yeh: Department of Chemistry, National Cheng Kung University, No. 1, Ta Hsueh Rd., Tainan 70101, Taiwan, ROC
Shin-Hun Juang: School 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.
Fung Fuh Wong: 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.

Journal volume & issue: Vol. 12, no. 8
pp. 1908 – 1917

Abstract

Read online

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

Published in Arabian Journal of Chemistry

ISSN: 1878-5352 (Print)
Publisher: Elsevier
Country of publisher: Netherlands
LCC subjects: Science: Chemistry
Website: http://www.journals.elsevier.com/arabian-journal-of-chemistry/

About the journal