62826-28-2Relevant academic research and scientific papers
Diastereoselective intramolecular meta photocycloaddition of side-chain- substituted 5-(2-methoxyphenyl)pent-1-enes
Timmermans, Johan L.,Wamelink, Marc P.,Lodder, Gerrit,Cornelisse, Jan
, p. 463 - 470 (2007/10/03)
Irradiation of a series of 5-(2-methoxyphenyl)pent-1-enes substituted with a hydroxy or trimethylsilyloxy group at the α-, β-, or γ-position of the side-chain yields in all cases meta photocycloadducts, in which the configuration at the substituted carbon atom is mainly endo. This indicates that the diastereoselectivity originates from minimization of steric interactions between the side-chain substituent and the ortho-methoxy group at the arene unit. Hydrogen bonding does not seem to be involved. The introduction of the side-chain substituents also influences the regioselectivity of the addition: The linear to angular adduct ratios are significantly increased compared to the case of the parent compound.
β-Adrenergic blocking agents: Substituted phenylalkanolamines. Effect of side-chain length on β-blocking potency in vitro
Fuhrer,Ostermayer,Zimmermann,Meier,Mueller
, p. 831 - 836 (2007/10/02)
The synthesis of a group of potential β-blockers bearing a new 5-ethoxysalicylamide substituent on nitrogen is described. These compounds were tested for β-adrenergic blocking potency in vitro and compared with analogous compounds bearing a tert-butyl group on nitrogen. The new N-substituent increased the β-blocking potency substantially. In a series of five homologous compounds of the type Ar(CH2)(n)CHOHCH2NHR (R = 5-ethoxysalicylamide; n = 0-4), two maxima of β-blocking potency were found for n = 0 and 2. Moreover, the carbon isostere of the corresponding (aryloxy)propanolamine still proved to be a very potent β-blocker. The ether oxygen in the side chain is therefore not an absolute requirement for activity. Structure-activity relationships are discussed.
