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M2613 is a nonsteroidal estrogen derived from triphenylbromoethylene which was studied for the treatment of breast cancer in women in the 1940s, but was never marketed.[1][2]

Chemistry

Synthesis

The chemical synthesis of M2613 has been described:[3]

The Grignard reaction between 1-(4-Ethoxyphenyl)-2-phenylethanone [38495-73-7] (1) and 4-Bromoanisole [104-92-7] (2) gives 3. Condensation with molecular bromine in the presence of glacial acetic acid completes the synthesis of M2613 (4). Alternately, Grignard reaction between 4-Ethoxy-4′-methoxybenzophenone [52886-92-7] (4) and benzyl bromide [100-39-0] (5) also yields 3.

See also

References

  1. ^ Walpole AL, Paterson E (October 1949). “Synthetic oestrogens in mammary cancer”. Lancet. 2 (6583): 783–6. doi:10.1016/s0140-6736(49)91370-7. PMID 15391512.
  2. ^ Jordan VC (February 2015). “The new biology of estrogen-induced apoptosis applied to treat and prevent breast cancer”. Endocr. Relat. Cancer. 22 (1): R1–31. doi:10.1530/ERC-14-0448. PMC 4494663. PMID 25339261.
  3. ^ Frederick Robert Basford, GB566415 (1944 to Imperial Chemical Industries Ltd).