Cytotoxic ester derivatives of the mammary tumor inhibiting antiestrogen 2,3-bis(2-fluoro-4-hydroxyphenyl)-2,3-dimethylbutane.

Abstract

The synthesis of the bis-acrylate 12, the bis-beta-chloropropionate 13 and the bis-beta-bromopropionate 14 of the "partial" antiestrogen 2,3-bis(2-fluoro-4-hydroxyphenyl)-2,3-dimethylbutane (7) is described. In the case of 13 and 14 the introduction of the beta-haloester-functions moderately reduces the estrogen receptor affinity of 7. However, it was quite strongly diminished in 12. The hydrolytic stability under in vitro-receptor-assay conditions decreases in the order 12 greater than 14 greater than 13. Compared with 7 the estrogenic potency of 12-14 is increased to a great extent. The title compounds cause a strong inhibition of the hormone-dependent MXT-M3.2 mouse mammary tumor.

• Authors: W Schwarz, R W Hartmann, J Engel, M R Schneider, H Schönenberger
• Journal: Archiv der Pharmazie (Arch Pharm (Weinheim)) Vol. 323 Issue 2 Pg. 121-4 (Feb 1990) ISSN: 0365-6233 [Print] Germany
• PMID: 2159273 (Publication Type: Journal Article)

Chemical References

• Antineoplastic Agents
• Estrogen Antagonists
• Hexestrol
• 2,3-bis(2-fluoro-4-hydroxyphenyl)-2,3-dimethylbutane

Topics

• Animals
• Antineoplastic Agents (chemical synthesis)
• Cattle
• Cell Survival (drug effects)
• Chemical Phenomena
• Chemistry
• Chromatography, High Pressure Liquid
• Estrogen Antagonists (chemical synthesis)
• Hexestrol (analogs & derivatives, chemical synthesis, pharmacology)
• In Vitro Techniques
• Mammary Neoplasms, Experimental (drug therapy)
• Mice