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: ジャーナルへの寄稿記事

抄録

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

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Bongkrekic Acid
ATP Translocases Mitochondrial ADP
Benzene
Chain length
Bearings (structural)
Carbon
Skeleton
Functional groups
Adenosine Triphosphate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

これを引用

Fujita, S., Suyama, M., Matsumoto, K., Yamamoto, A., Yamamoto, T., Hiroshima, 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

Synthesis and evaluation of simplified functionalized bongkrekic acid analogs. / Fujita, Satoshi; Suyama, Masaki; Matsumoto, Kenji; Yamamoto, Atsushi; Yamamoto, Takenori; Hiroshima, Yuka; Iwata, Takayuki; Kano, Arihiro; Shinohara, Yasuo; Shindo, Mitsuru.

:: Tetrahedron, 巻 74, 番号 9, 01.03.2018, p. 962-969.

研究成果: ジャーナルへの寄稿記事

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, 巻. 74, 番号 9, pp. 962-969. https://doi.org/10.1016/j.tet.2018.01.018
Fujita S, Suyama M, Matsumoto K, Yamamoto A, Yamamoto T, Hiroshima Y その他. Synthesis and evaluation of simplified functionalized bongkrekic acid analogs. Tetrahedron. 2018 3 1;74(9):962-969. https://doi.org/10.1016/j.tet.2018.01.018
Fujita, Satoshi ; Suyama, Masaki ; Matsumoto, Kenji ; Yamamoto, Atsushi ; Yamamoto, Takenori ; Hiroshima, Yuka ; Iwata, Takayuki ; Kano, Arihiro ; Shinohara, Yasuo ; Shindo, Mitsuru. / Synthesis and evaluation of simplified functionalized bongkrekic acid analogs. :: Tetrahedron. 2018 ; 巻 74, 番号 9. pp. 962-969.
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AU - Hiroshima, Yuka

AU - Iwata, Takayuki

AU - Kano, Arihiro

AU - Shinohara, Yasuo

AU - Shindo, Mitsuru

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