68266-24-0

Upstream product

• 37951-49-8 1-(3-methoxyphenyl)propan-1-one 
• 52956-27-1 1-(3-methoxyphenyl)propanol 
• 68266-31-9 1-chloro-1-(3-methoxyphenyl)propane 
• 591-31-1 3-methoxy-benzaldehyde 
• 68266-30-8 (+/-)-3,4-Bis<3-methoxyphenyl>-hexane 
• 76473-05-7 C₂₀H₂₄O₂ 
• 68266-30-8 metahexestrol dimethyl ether 

Downstream Products

• 89106-19-4 meso-3,4-bis(4-bromo-3-hydroxyphenyl)hexane 
• 89106-20-7 meso-3,4-bis(3-hydroxy-4-iodophenyl)hexane 
• 89106-27-4 meso-3,4-bis(3-hydroxy-4-nitrophenyl)hexane 
• 89106-21-8 meso-3,4-bis[4-[(dimethylamino)methyl]-3-hydroxyphenyl]hexane 
• 89106-24-1 meso-3,4-bis<3-acetoxy-4-(acetoxymethyl)phenyl>hexane 
• 89106-25-2 C₂₄H₃₄O₄ 
• 89106-23-0 meso-3,4-bis[3-hydroxy-4-(methoxymethyl)phenyl]hexane 
• 89106-26-3 C₂₀H₂₆O₄ 
• 89106-22-9 meso-3,4-bis(3-hydroxy-4-methylphenyl)hexane 

Relevant academic research and scientific papers

Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 2. Synthesis and estrogen receptor binding affinity of 4,4'-, 5,5'-, and 6,6'-disubstituted metahexestrols

The synthesis of symmetrically 4,4'-, 5,5'-, and 6,6'-disubstituted derivatives of the mammary tumor inhibiting antiestrogen metahexestrol [meso-3,4-bis(3-hydroxyphenyl)hexane] (1) are described [4,4'-disubstituents: F(2), Cl (3), Br (4), I (5), CH2N(CH3)2 (6), CH3 (7), CH2OCH3 (8), CH2OC2H5 (9), CH2OH (10), NO2 (11), NH2 (12), N(CH3)2 (13), COCH3 (14), and C2H5 (15); 5,5'-substituents: OH (16) and Cl (17); 6,6'-disubstituents: OH (18), F (19), Cl (20), and CH3 (21)]. The synthesis of 1-3, 16, and 19 was accomplished by reductive coupling of the propiophenones with TiCl4/Zn and subsequent hydrogenation of the cis-3,4-diphenylhex-3-enes. Compounds 17, 18, 20, and 21 were synthesized by coupling the 1-phenyl-1-propanols with TiCl3/LiAlH4 and separation of the meso diastereomers, while 4-15 were obtained by substitution of metahexestrol. The binding affinity of these compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. The test compounds showed relative binding affinity (RBA) values between 15 and 0.5% were evaluated in the mouse uterine weight test. They showed a similar (2 and 12), slightly increased (19 and 21), or strongly enhanced (7 and 20) estrogenicity compared to that of metahexestrol. Compounds 1, 2, 7, 12, and 21 exhibited antiestrogenic activity inhibiting the estrone-stimulated uterine growth (24 to 60% inhibition).

Potential Antiestrogens. Synthesis and Evaluation of Mammary Tumor Inhibiting Activity of 1,2-Dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes

The syntheses of the meso-1,2-dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes and of d,l-3,4-bis(3'-hydroxyphenyl)hexane (21) are described.In vitro these compounds inhibited the estradiol receptor interaction competitively, exhibiting Ka values between 0.20*109 (20) and 0.11*106 M-1 (24).In vivo the meso compounds reduced the estrone-stimulated mouse uterine growth; the most effective compounds were 20, 22, and 23 (53, 50, and 45percent inhibition, respectively).Compounds 20 and 22-24 showed weak estrogenic activity in the mouse uterine weight test and in the vaginal cornification test.Compounds 19 (NSC-297169), 20 (NSC-297170), and 22 (NSC-297171) exhibited a dose-dependent growth inhibition on the MCF-7 human breast tumor cell line (10-6 to 10-9 M).These compounds also showed a marked dose-dependent inhibition on the DMBA-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat corresponding to their association constants.

Novel di-(3'-hydroxyphenyl)-alkane compounds, process of preparation and their use in medicine

Compounds of di-(3'-hydroxyphenyl)-alkanes and their methyl ethers, of the formula STR1 wherein R is alkyl and R' is H or methyl, have activity against hormone-dependent breast carcinoma.