127399-79-5Relevant academic research and scientific papers
Rh(II)-Catalyzed Synthetic Strategy for Diverse and Functionalized Halonaphthalenyl Ethers and Esters from Diazo Compounds and Its Application to Polyaromatic Compounds
Baral, Ek Raj,Lee, Yong Rok,Kim, Sung Hong,Wee, Young-Jung
, p. 579 - 587 (2016/02/12)
An efficient and simple synthesis of various functionalized halonaphthalenyl ethers and esters in moderate to good yield was achieved via rhodium(II)-catalyzed reaction of readily available diazo compounds with benzyl halides or acid halides. This methodology has several advantages, such as ease of handling, mild reaction conditions, bromine- or chlorine-free route, and the use of an effective catalyst. The synthesized compounds were further converted into valuable polyaromatic compounds using the Suzuki reaction.
Lead optimization of 17β-HSD1 inhibitors of the (hydroxyphenyl) naphthol sulfonamide type for the treatment of endometriosis
Henn, Claudia,Einspanier, Almuth,Marchais-Oberwinkler, Sandrine,Frotscher, Martin,Hartmann, Rolf W.
supporting information; experimental part, p. 3307 - 3318 (2012/06/01)
The reduction of estrone to estradiol, the most potent estrogen in human, is catalyzed by 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1). A promising approach for the treatment of estrogen-dependent diseases is the reduction of intracellular estradiol formation by inhibition of 17β-HSD1. For the species-specific optimization of the (hydroxyphenyl)naphthols, a combinatorial approach was applied and enhanced by a focused synthesis that resulted in the aromatic-substituted (hydroxyphenyl)naphthol sulfonamides. Rigidification of 12 led to the 4-indolylsulfonamide 30, which is a highly active and selective human 17β-HSD1 inhibitor, as well as a highly potent and selective inhibitor of 17β-HSD1 from Callithrix jacchus. It shows no affinity to the estrogen receptors I?± and β and good intracellular activity (T47D). Thus, compound 30 shows good properties for further ADMET studies and might be a candidate for the in vivo proof of concept in C. jacchus.
Monomethyl Ether Derivatives of 7,8-Dihydroxy- and 8,9-Dihydroxy-4-n-propyl-1,2,3,4,4a,5,6,10b-octahydrobenzoquinolines as Possible Products of Metabolism by Catechol-O-methyltransferase
Cannon, Joseph G.,Walker, Kathleen A.,Montanari, Antonio,Long, John Paul,Flynn, Jan R.
, p. 2000 - 2006 (2007/10/02)
In order to facilitate identification of possible metabolites arising from in vitro action of catechol-O-methyltransferase upon 7,8-dihydroxy- and 8,9-dihydroxy-4-n-propyl-1,2,3,4,4a,5,6,10b-octahydrobenzoquinolines (11, 12), all four possible monomethyl ether derivatives have been synthesized.Incubation of 11 and 12 with the enzyme revealed that the 8,9-dihydroxy positional isomer 12 (which contains the dopamine moiety held in the β conformation) but not the 7,8-dihydroxy isomer 11 (which holds the dopamine moiety in the α conformation) was a substrate for theenzyme.The sole detectable product of 12 was 8-hydroxy-9-methoxy derivative 15 in which the "meta" hydroxy group of the dopamine moiety is etherified.
