Synthesis of Spiro[cyclohexane-1,2'-[2H]indene] Derivatives as Inhibitors of Steroid 5α-Reductase

    June 1995 in “ Helvetica Chimica Acta
    Shu‐Kun Lin, Vittorio Rasetti
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    TLDR Compound 15a was effective in inhibiting 5α-reductase.
    In a 1995 study, researchers created spiro[cyclohexane-1,2'-[2H]indene] derivatives, particularly compounds 15a and b, aiming to inhibit steroid 5α-reductase, which is linked to benign prostatic hyperplasia and androgenic alopecia. The synthesis process started with 5-methoxyindan-1-one and involved several chemical reactions, including a Grignard reaction, dehydration, and hydrogenation, leading to the desired compounds. A key intermediate was spiro[cyclohexane-1,2'-[2H]indene]-1'(3'H),4-dione (5). These compounds were structured to resemble the shape and nucleophilic groups of existing 5α-reductase inhibitors. The study concluded that compound 15a was effective as a 5α-reductase inhibitor, but the specific biological test results were to be published separately. This was a chemical synthesis study, so the number of participants was not applicable.
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