De Novo Synthesis of Possible Candidates for the Inagami–Tamura Endogenous Digitalis-like Factor

• Nakazaki, Atsuo

• Hashimoto, Keiko

• Ikeda, Ai

• Shibata, Takahiro

• Nishikawa, Toshio

抄録

De novo synthesis of possible candidates for the Inagami–Tamura endogenous digitalis-like factor (EDLF) was achieved to validate a previously proposed structure. Our synthetic approach involves a highly regio- and diastereoselective Mizoroki–Heck reaction and a Friedel–Crafts-type cyclodehydration to construct steroidal tetracycle 14 as a versatile common intermediate leading to seven 2,14β-dihydroxyestradiol analogues 1a–c, 2a–c, and 3 as possible candidates. By comparing the potency of inhibitory activity against Na+/K+-ATPase between the synthesized candidates and the EDLF, it was found that the proposed structure is not likely to be a true structure of the Inagami–Tamura EDLF.

収録刊行物

• The Journal of Organic Chemistry

  The Journal of Organic Chemistry 82 (17), 9097-9111, 2017-09

  ACS Publications

キーワード

• Organic Chemistry

詳細情報

• CRID: 1050564288759320576
• NII論文ID: 120006367971
• DOI: 10.1021/acs.joc.7b01640
• ISSN: 15206904
• ISSN: 00223263
• HANDLE: 2237/27149
• Web Site: https://nagoya.repo.nii.ac.jp/records/24928
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/acs.joc.7b01640
• 本文言語コード: en
• 資料種別: journal article
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