M2613

M2613

Clinical data
Other names	M-2613; Methoxyethoxy-triphenylbromoethylene
Drug class	Nonsteroidal estrogen
Identifiers
IUPAC name 1-Bromo-2-(p-ethoxyphenyl)-2-(p-methoxyphenyl)-1-phenylethylene
CAS Number	114795-29-8
Chemical and physical data
Formula	C23H21BrO2
Molar mass	409.323 g·mol−1
3D model (JSmol)	Interactive image
SMILES c1ccccc1C(Br)=C(c1ccc(OC)cc1)c1ccc(OCC)cc1
InChI InChI=InChI=1S/C23H21BrO2/c1-3-26-21-15-11-18(12-16-21)22(17-9-13-20(25-2)14-10-17)23(24)19-7-5-4-6-8-19/h4-16H,3H2,1-2H3 Key:SPHDSWQIYGZLBR-UHFFFAOYSA-N

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]}

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

• Estrobin

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).