Synthesis and evaluation of 1,.omega.-diaryl-1,.omega.-alkanediamines related to the fibrinolytic bis(tetrahydroisoquinolines) and bis(benzylamines)

Abstract

Since the previously investigated bis(tetrahydroisoquinolines) 1 and bis(benzylamines) 2 may be classified as 1,omega-diaryl-1,omega-alkanediamines, it appeared worthwhile to examine this structural concept as a guideline for predicting significant fibrinolytic activity. The prototype bis compounds 7, 14, 15, and 29-31, which were synthesized for this purpose, incorporate such molecular modifications as replacement of the tetrahydroisoquinoline nuclei of series 1 with tetrahydrobenzazepine (7) and tetrahydropyridoindole (14-15) nuclei. The latter compounds, as well as 29-31 which possess features common to both series 1 and 2, showed good to moderate activity in the standard rat (ip) screen. Significant departures from the 1,omega-diaryl-1,omega-alkanediamine structural concept led to compounds (35 and 40) of weak to moderate activity.

Octahydro[1,4:5,8]dimethanoanthraquinone as a Cheap and Readily Avail­able Electron-Transfer Oxidant for Biaryl Synthesis from Organocuprates

“…However, attempted preparation of the 9-and 10-membered macrocycles 11d and 11e via oxidative cyclization of 10d 16 and 10e, 17 according to the procedure in Equation 3, yielded only a complex mixture of products; and the mass spectral analysis of the soluble components of these mixtures did not show the presence of 11d and 11e (Scheme 2).…”

“…2-Bromoanisole, 4-bromoanisole, bromobenzene, and 2-bromo-m-xylene were commercially available. 2-Bromo-4,4¢-di-tert-butylbiphenyl, 13 2-tertbutyl-4,5-dimethoxybromobenzene, 20 a,w-bis(dimethoxyphenyl)alkanes 10d 16 and 10e 17 were prepared according to the literature procedures.…”