164399-47-7Relevant articles and documents
Synthesis and &β-adrenoceptor blocking activity of some aryloxy- and benzyloxy-propanolamines
Marwah, A. K.,Marwah, Padma,Rao, G. Shankar,Trivedi, B. S.,Rao, B. E.,et al.
, p. 197 - 200 (2007/10/02)
4-(3-Thienyl)phenoxypropanolamines 9a-n and 4-(3-thienyl)benzyloxypropanolamines 10a-n have been synthesised starting from 3-(p-tolyl)thiophene (1) and 3-(4-methoxyphenyl)thiophene (2).Compound 1 on treatment with N-bromosuccinimide in refluxing CCl4 using dibenzoylperoxide or 2,2'-azobis(2-methylpropionitrile) as a catalyst gives 4-(3-thienyl)benzyl bromide (4) which on refluxing with AcOK/AcOH yields 4-(3-thienyl)benzyl acetate (5).The acetate 5 on hydrolysis furnishes 4-(3-thienyl)benzyl alcohol (6).Further, 3,4-(methoxyphenyl)thiophene (2) on demethylation yields 4-(3-thienyl)phenol (3).The phenol (3) and alcohol 6 on treatment with epichlorohydrin undergo alkylation to give 2,3-epoxy-4-(3-thienyl)phenoxypropane (7) and 2,3-epoxy-4-(3-thienyl)benzyloxypropane (8) respectively which on condensation with various amines in refluxing ethanol furnish 4-(3-thienyl)phenoxypropanolamines (9) and 4-(3-thienyl)benzyloxypropanolamines (10) respectively.Compounds 9 and 10 have been evaluated for their β-adrenergic blocking activity and a few of them shown moderate β-adrenergic blocking activity.