Abbauende Enzyme des Bindegewebes

Synthesis and antihypertensive activity of some thienylethanolamines

“…The ethereal extract was washed with water and saturated saline solution, dried (MgS04), and concentrated. The title compound was obtained in 947c yield as a colorless oil which crystallized on standing: mp 62-63°; ir (CHC13) 3540 cm'1; NMR (CDC13) 2.75 (d, J = 4 Hz, 1 H, OH), 3.58 (m, 2 H, CH2Br), 5.05 (m, 1 H, CHO), 6.9 (s, 1 H, C=CH). 2,5-Dichloro-a-(isopropylaminomethyl)-3thiophenemethanol was synthesized from bromothiophene-Bagli et al…”

“…23 The NMR (CDC13) exhibited 1.05 (d, J = 6 Hz, 6 H, CCH3), 2.83 (m, 3 H, CHN), 4.78 (m, 1 H, CHO), and 6.90 (s, 1 H, aromatic H). The hydrochloride was prepared in the usual manner and crystallized from ethyl acetate-methanol (637c yield): NMR (Me2SO-d6) 1.3 (d, J = 6.5 Hz, 6 H, CCH3), 2.9-S.7 (m, 3 H, CHN), 5.1 (m, 1 H, CHO), 6.4 (m, 1 H, OH), 7.25 (s, 1 H, C=CH), 9.2 (broad, 2 H, NH2+). Anal.…”

“…The hydrochloride 20 of the base (2.32 g) was prepared in the usual manner to give a brown solid Bromomethyl-5-methyl-2-thienylmethanol (5.0 g) described above and d-(3,4-dimethoxyphenyl)ethylamine (6.2 g) were refluxed in dioxane for 3 h. The mixture was cooled to room temperature, diluted with chloroform (200 ml), washed with 107c sodium hydroxide and water, and dried, and the solvent was evaporated. The residual oil (11.4 g) was chromatographed to yield pure isomer A [2.36 g (34%); NMR (CDC13) 2.45 (s, 3 H, »CCH3), 3.0 (m, 6 H, CH2N, CH2C=C), 3.85 (s, 6 H, CH30), 4.45 (broad, 2 , OH, NH), 5.1 (t, J = 6 Hz, CH20), 6.8 (m, 5 H, aromatics)] and isomer B [2.63 g (35%); NMR (CDC13) 2.27 (s, 2 H, CH2Ar), 2.47 (s, 3 H, >CCH3), 2.8 (m, 3 H, CHN), 3.7 (m, 2 H, CH20), 3.87 (m, 6 H, CH30), 6.75 (m, 5 H, aromatics)].…”

“…The solution was allowed to stand at room temperature for 2 h and cooled in an ice bath, and the crystals were filtered. Isomer A yielded (507c) oxalate 21: mp 108-110°; NMR (Me2SO-de) 2.45 (s, 3 H, C=CCH3), 2.9 (broad, 4 H, CH2N, CH2C=C), 3.75 (s, 6 H, CH30), 3.82 (m, 2 H, CH20), 4.55 (m, 1 H, CHN), 6. -7.2 (m, 5 H, aromatics), 8.25 (broad, 4 H, OH, NH2+, COOH).…”

“…-7.2 (m, 5 H, aromatics), 8.25 (broad, 4 H, OH, NH2+, COOH). Isomer B gave oxalate 10 (507o): mp 160°; NMR (Me2SO-c¡6) 2.42 (s, 3 H, C=CCH3), 3.1 (m, 6 H, CH2N, CH2C=C), 3.78 (s, 6 H, CH30), 5.2 (m, 1 H, CHO-), 6.8 (m, 5 H, aromatics), 8.3 (broad, a-bromomethyl-5-methyl-2-thienylmethanol (5.0 g) in toluene (100 ml) was allowed to react with 3,4-methylenedioxyphenethylamine obtained from the corresponding hydrochloride 2 (6.5 g) at reflux temperature for 8 h. The basic products were isolated and purified by chromatography to yield n-(3,4-methylenedioxyphenethylaminomethyl)-5-methyl-2-thienylmethanol (1.74 g, 25%): mp 93-94°; NMR (CDC13) 2.42 (s, 3 H, CH3C<), 2.8 (m, 6 H, CH2N, CH2C=C), 3.1 (s, 2 , NH, OH), 4.9 (t, J = 6 Hz, 1 H, CHO-), 5.9 (s, 2 H, 0CH20), 6.7 (m, 5 H, aromatics). The hydrochloride 12 was prepared in the usual manner and crystallized from methyl ethyl ketone-methanol-ether: mp 183-185°; NMR b 2.49 (s, 3 H, CH3C«), 3.1 (m, 6 H, CH2N, CH2C=C), 5.25 (m, 1 H, CHO-), 6.0 (m, 2 H, CH20), 6.6-7.2 (m, 5 H, aromatics).…”