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Synthesis and antileishmanial activity of the core structure of cristaxenicin A.
Fumiyama, Hitoshi; Sadayuki, Tomoko; Osada, Yasutaka; Goto, Yasuyuki; Nakao, Yoichi; Hosokawa, Seijiro.
Affiliation
  • Fumiyama H; Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
  • Sadayuki T; Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
  • Osada Y; Department of Animal Resource Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo, Tokyo 1138657, Japan.
  • Goto Y; Department of Animal Resource Sciences, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo, Tokyo 1138657, Japan.
  • Nakao Y; Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan; Research Institute for Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
  • Hosokawa S; Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan; Research Institute for Science and Engineering, Waseda University, Ohkubo 3-4-1, Shinjuku, Tokyo 1658555, Japan.
Bioorg Med Chem Lett ; 26(17): 4355-7, 2016 09 01.
Article in En | MEDLINE | ID: mdl-27476143
The core structure of cristaxenicin A having trans-fused dihydropyran and nine membered ring has been synthesized and evaluated the antileishmanial activity. The dihydropyran ring was synthesized by [4+2] cycloaddition reaction between an unsaturated aldehyde and a ß-alkoxy-α,ß-unsaturated ketone. The nine membered ring possessing α,ß-unsaturated aldehyde was constructed by the intramolecular NHK reaction followed by the Mitsunobu rearrangement. The racemic core structure of cristaxenicin A was evaluated the anti-leishmanial activity with an IC50 value of 2.4µM.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Diterpenes / Leishmania Language: En Journal: Bioorg Med Chem Lett Journal subject: BIOQUIMICA / QUIMICA Year: 2016 Type: Article Affiliation country: Japan

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Diterpenes / Leishmania Language: En Journal: Bioorg Med Chem Lett Journal subject: BIOQUIMICA / QUIMICA Year: 2016 Type: Article Affiliation country: Japan