Schwarz, Walter and Hartmann, Rolf W. and Engel, Juergen and Schneider, Martin R. and Schönenberger, Helmut (1990) Cytotoxic ester derivatives of the mammary-tumor-inhibiting antiestrogen 2,3-bis(2-fluoro-4-hydroxyphenyl)-2,3-dimethylbutane. Archiv der Pharmazie 323 (2), pp. 121-124.
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The synthesis of the bisacrylate I (R = CH2:CHCO2) (II), the bis-beta -chloropropionate I (R = ClCH2CH2CO2) (III) and the bis-beta -bromopropionate I (R = BrCH2CH2CO2) (IV) of the partial antiestrogen 2,3-bis(2-fluoro-4-hydroxyphenyl)-2,3-dimethylbutane I (R = OH) (V) by condensation V with corresponding acid chloride is described. In the case of III and IV the introduction of the beta -haloester functions moderately reduces the estrogen receptor affinity of V. However, it was quite strongly diminished in II. The hydrolytic stability under in vitro-receptor-assay conditions decreases in the order II > IV > III. Compared with the V the estrogenic potency of II-IV is increased to a great extent. The title compds. cause a strong inhibition of the hormone-dependent MXT-M3.2 mouse mammary tumor.
|Additional information (public):||CAN 113:5844 25-18 Benzene, Its Derivatives, and Condensed Benzenoid Compounds 625-36-5; 814-68-6 (2-Propenoyl chloride); 15486-96-1 Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with bis(fluorohydroxyphenyl)dimethylbutane); 96826-17-4 Role: RCT (Reactant), RACT (Reactant or reagent) (condensation with acrylic and halopropionic acid chlorides and hydrolytic stability of, estrogen receptor affinity in relation to); 110300-86-2; 110300-87-3; 110300-88-4; 110300-89-5 Role: RCT (Reactant), RACT (Reactant or reagent) (hydrolytic stability of, estrogen receptor affinity in relation to); 127530-38-5P; 127530-39-6P; 127530-40-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogenic activity of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Estrogens Role: USES (Uses) (inhibitors, bis(fluorohydroxyphenyl)dimethylbutane derivs.) bisfluorohydroxyphenyldimethylbutane deriv prepn antiestrogen activity estrogen inhibitor fluorohydroxyphenyldimethylbutane deriv|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Deposited On:||12 Nov 2010 07:17|
|Last Modified:||12 Nov 2010 07:17|