59515-92-3

Upstream product

• 24039-89-2 5,6-dimethoxy-1-tetralone 
• 7440-44-0 pyrographite 
• 81580-84-9 4-(2',3'-dimethoxyphenyl)-3-butenoic acid 
• 64400-76-6 4-(2',3'-dimethoxyphenyl)-3-butanoic acid 

Downstream Products

• 84854-57-9 5,6-methylenedioxy-3,4-dihydro-1(2H)-naphthalenone 
• 144619-97-6 5-benzyloxy-6-methoxy-1-tetralone 
• 59515-93-4 5,6-bis(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one 
• 59515-99-0 (1R,2R)-2-(benzyl(methyl)amino)-5,6-bis(benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-ol 

Relevant academic research and scientific papers

BETA-2 SELECTIVE ADRENERGIC RECEPTOR AGONISTS

Aspects of the present disclosure include conformationally restricted analogs of catecholamine type compounds (e.g., isoprenaline, adrenaline, noradrenaline) which activate β2AR with high selectivity over β1AR. The subject beta-2 selective adrenergic rece

Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone

The risk factors for women developing breast and endometrial cancers are all associated with a lifetime of estrogen exposure. Estrogen replacement therapy in particular has been correlated with an increased cancer risk. Previously, we showed that the equine estrogens equilin and equilenin, which are major components of the widely prescribed estrogen replacement formulation Premarin, are metabolized to highly cytotoxic quinoids which caused oxidative stress and alkylation of DNA in vitro [Bolton, J. L., Pisha, E., Zhang, F., and Qiu, S. Chem. Res. Toxicol. 1998, 11, 1113-1127]. In this study, we have synthesized 8,9-dehydroestrone (a third equine estrogen component of Premarin) and its potential catechol metabolites, 4-hydroxy-8,9-dehydroestrone and 2-hydroxy-8,9-dehydroestrone. Both 2-hydroxy-8,9-dehydroestrone and 4-hydroxy-8,9-dehydroestrone were oxidized by tyrosinase or rat liver microsomes to o-quinones which reacted with GSH to give one mono-GSH conjugate and two di-GSH conjugates. Like endogenous estrogens, 8,9-dehydroestrone was primarily converted by rat liver microsomes to the 2-hydroxylated rather than the 4-hydroxylated o-quinone GSH conjugates; the ratio of 2-hydroxy-8,9-dehydroestrone versus 4-hydroxy-8,9-dehydroestrone was 6:1. Also in contrast to experiments with equilin, 4-hydroxyequilenin was not observed in microsomal incubations with 8,9-dehydroestrone or its catechols. The behavior of 2-hydroxy-8,9-dehydroestrone was found to be more complex than 4-hydroxy-8,9-dehydroestrone as GSH conjugates resulting from 2-hydroxy-8,9-dehydroestrone were detected even without oxidative enzyme catalysis. Under physiological conditions, 2-hydroxy-8,9-dehydroestrone isomerized to 2-hydroxyequilenin to form the very stable 2-hydroxyequilenin catechol; however, 4-hydroxy-8,9-dehydroestrone was found to be stable under similar conditions. Finally, preliminary studies conducted with the human breast tumor S-30 cell lines demonstrated that the catechol metabolites of 8,9-dehydroestrone were much less toxic than 4-hydroxyequilenin (20-40-fold). These results suggest that the catechol metabolites of 8,9-dehydroestrone may have the ability to cause cytotoxicity in vivo primarily through formation of o-quinones; however, most of the adverse effects of Premarin estrogens are likely due to formation of 4-hydroxyequilenin o-quinone from equilin and equilenin.

1-AMINOMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENES

Compounds of the formula STR1 and pharmaceutically acceptable salt thereof, wherein R 2 is selected from hydroxy and lower alkoxy, R 5 is lower alkyl, and R 11 and R 12 are independently selected from hydrogen, halo, hydroxy, methoxy, and lower alkyl, are selective . alpha.. sub.2 adrenergic receptor antagonists useful in the treatment of glaucoma.

1-aminomethyl-1,2,3,4-tetrahydronaphthalenes

The present invention provides compounds of the formula STR1 or a pharmaceutically acceptable salt thereof wherein R1 is selected from hydrogen, halo, lower alkyl, lower alkoxy, or thioalkoxy; and R2 is lower alkoxy; or R1 and R2 together form a methylenedioxy or ethylenedioxy ring; R3 and R4 are independently selected from hydrogen, hydroxy, lower alkyl, lower alkoxy, lower alkylthio, (lower alkyl)amino, (lower alkylsulfonyl)amino, and halo; and R7 is selected from the group consisting of 2- or 3-thienyl, 2- or 3-furyl, and STR2 where R13 and R14 are independently selected from the group consisting of hydrogen, hydroxy, halogen, amino, lower alkyl, lower alkoxy, lower alkylthio, methylenedioxy, or ethylenedioxy. The compounds of the present invention selectively inhibit α2 -adrenergic receptors as well as inhibit the uptake of biogenic amines and are thus useful in the treatment of certain cardiovascular and psychiatric disorders.