56724-08-4

Upstream product

• 3168-59-0 5-methoxy-o-toluic acid 

Downstream Products

• 85681-43-2 5-Methoxy-2-methyl-benzoic acid hydrazide 
• 85681-47-6 3-(5-Methoxy-2-methyl-phenyl)-5-phenyl-1H-[1,2,4]triazole 
• 85681-48-7 3-(5-Methoxy-2-methyl-phenyl)-5-(3-methoxy-phenyl)-1H-[1,2,4]triazole 
• 89106-51-4 C₂₂H₃₀O₂ 
• 89106-50-3 C₂₀H₂₆O₂ 
• 89106-52-5 1-(5-Methoxy-2-methyl-phenyl)-propan-1-ol 
• 29578-81-2 3-Methoxy-6-methyl-propiophenon 
• 56724-09-5 5-methoxy-2-methylbenzaldehyde 

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).

A New Class of Nonhormonal Pregnancy-Terminating Agents. Synthesis and Contragestational Activity of 3,5-Diaryl-s-triazoles

A series of 3,5-diaryl-s-triazoles were synthesized and evaluated as postimplantation contragestational agents.The introduction of various substituents (e.g., an o-alkyl chain on one phenyl and a m-alkoxy group on the other) was found to increase the potency.Several compounds with very high pregnancy-terminating activity in both hamsters and rats were obtained.One of these, 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-s-triazole, DL 111 (36), was selected for detailed evaluation in various animal species.A synthetic scheme for the preparation of these compounds and preliminary structure-activity relationships are presented.