Synthesis, antiulcer and antidepressive activity of 4-(4-halophenyl)-2-phenyl-1,2,3,4-tetrahydroisoquinolines.

4-(4-halophenyl)-2-methyl-1,2,3,4-tetrahydro-isoquinolines 2a-c have been synthesized by two methods and their biochemical and pharmacological properties have been studied. Biochemical investigations showed that all the compounds are strong inhibitors of DA, NE and 5-HT reuptake, the strongest effect being observed with compound 2b (R = Br). 2a-c exhibited a strong antiulcer activity on an experimental model of stress-induced ulcers with minimal doses (0.

Resolution and absolute stereochemistry of 6,7-dimethoxy-4-phenyl- 1,2,3,4-tetrahydroisoquinoline. The crystal structure of the R-hydrochloride salt form.

Stereospecific multistep synthesis and resolution of 6,7-dimethoxy-4- phenyl-1,2,3,4-tetrahydroisoquinoline (3) has been achieved from its racemic base. The absolute configurations of the optical antipodes converted into their hydrochloride salt forms have been determined by X-ray diffractometric analysis, thus permitting assignment of the antipodes as the (+)-(4R)-3 and (-)-(4S)-3 enantiomers. The crystal structures of the two enantiomers are related as mirror images and only the (4R)-3.

[Racemic and optically active 2-chloroethylcarbamoyl derivatives of 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine: a new structural type of DA, NE and 5-T uptake inhibitors].

The racemic and optically active 2-chloroethylcarbamoyl derivatives of 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines 6 and 8 were synthesized. The enantiomers of the benzazepine 5 were obtained by consecutive treatment of (+/-)-5 with (-) and (+)-dibenzoyl-tartaric acids. Compounds 6 are strong DA and NE uptake inhibitors while 8 exhibits inhibition towards 5-HT.

[A simple method of synthesis of S-sulfoxides of penicillanic acid and 6-alpha-bromo[chloro]-penicillanic acids].

A simple method for synthesis of S-sulfoxides of penicillanic acid and 6 alpha-bromo- and 6 alpha-chloropenicillanic acids is described. The S-sulfoxides were synthesized by the respective oxidation with 30% hydrogen peroxide at 0 degrees C in the absence of solvents. 1 mol of penicillanic acid and 1.

A new class of antiulcer drugs. I. Antiulcer effect of AN5, a 4-phenyl-tetrahydroisoquinoline derivative, on different experimental models of ulcer in rats.

The action of AN5 on experimental models of gastric ulcers induced by water-immersion stress, indomethacin and reserpine, or by pylorus ligation in rats has been studied. AN5 supresses the formation of ulcers in all experimental models. The strongest antiulcer effect is shown in relation to water-immersion stress-induced ulcers.

[Synthesis, stereochemistry and anticonvulsant action of 4-phenyltetrahydroisoquinolines].

The racemic and optically active 4'- and 8-substituted tetrahydroisoquinolines 2-5 have been synthesized and their effect on the water-immersion stress ulcer in rats has been studied. All compounds prevent the formation of stress ulcer, the strongest effect being exhibited by compound 4 and its dextrarotatory isomer (R1 = Cl, R2 = NHCOOC2H5). The antiulcer activity of 4 is 30 to 50 times higher than that of the H2 receptor antagonists Cimetidin and Ranitidin used for comparison.