Synthesis and evaluation of simplified functionalized bongkrekic acid analogs

Satoshi Fujita, Masaki Suyama, Kenji Matsumoto, Atsushi Yamamoto, Takenori Yamamoto, Yuka Hiroshima, Takayuki Iwata, Arihiro Kano, Yasuo Shinohara, Mitsuru Shindo

研究成果: Contribution to journalArticle

抜粋

Bongkrekic acid (BKA) is a strong inhibitor of adenine nucleotide translocase (ANT), inducing inhibition of adenosine triphosphate synthesis. We designed and synthesized simplified benzene-ring-containing BKA analogs. The key reaction is the one-pot double Sonogashira reaction, which forms the main skeleton. The analogs were efficiently synthesized in 8–10 longest linear sequence steps. This synthetic method can be applied for the preparation of other analogs having different combinations of carbon chain lengths. Furthermore, the allyloxy group on the benzene ring can be easily replaced by other functional groups. Our preliminary biological evaluation based on mitochondrial inhibitory effects revealed the high potency of the analogs bearing the same carbon chain length as that of BKA. In particular, the prefunctionalized analogs are potential ANT inhibitors.

元の言語英語
ページ(範囲)962-969
ページ数8
ジャーナルTetrahedron
74
発行部数9
DOI
出版物ステータス出版済み - 3 1 2018

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Fujita, S., Suyama, M., Matsumoto, K., Yamamoto, A., Yamamoto, T., Hiroshima, Y., Iwata, T., Kano, A., Shinohara, Y., & Shindo, M. (2018). Synthesis and evaluation of simplified functionalized bongkrekic acid analogs. Tetrahedron, 74(9), 962-969. https://doi.org/10.1016/j.tet.2018.01.018