A Preliminary Study On The Synthesis Of The Original Hematoxylin A And Its Intermediates

Protosappanin A is an active ingredient extracted from Sappan Lignum, which is a kind of traditional Chinese medicine. It has been found to have the function against rejection after allograft heart transplantation and anti-cancer activity in the study at present. The total synthesis about it has not yet been reported in the literature. In this paper, the total synthesis of Protosappanin A was researched preliminarily. At the same time, several novel compounds of bipheys were prepared and screening of biological activity was discussed. First, six biphenyl derivatives were designed and synthesized from o-methoxy phenol and resorcinol as raw materials:2,3’,4,4’-tetramethoxybiphenyl, biphenyl-2,3’,4,4’-tetrayltetraacetate,1-(2’,4,4’,5-tetramethoxybiphenyl-2-yl)propan-2-on e,1-(2’,4’-dihydroxy-4,5-dimethoxybiphenyl-2-yl)propan-2-one,2-(2’,4,4’,5-tetramethoxy biphenyl-2-yl)acetic acid and methyl 2-(2’,4,4’,5-tetramethoxybiphenyl-2-yl)acetate.Sec ond, eight membered ring were use constructed through three different routes by 3,4-dimethoxyphenylacetic acid as raw materials, and five intermediates were synthesized: 1-bromo-3-(2’,4,4’,5-tetramethoxybiphenyl-2-yl)propan-2-one,1-(2’-(benzyloxy)-4,4’,5-trim ethoxybiphenyl-2-yl)3-hydroxypropan-2-one,1-(2’-(benzyloxy)-4,4’,5-trimethoxybiphen yl-2-yl)3-bromopropan-2-one,1-(2’-hydroxy-4,4’,5-trimethoxybiphenyl-2-yl)-3-methoxy propan-2-one and ethyl-2(-4,4’,5-trimethoxy-2’-(2-methoxy-2-oxoethyl)biphenyl-2-ylo xy)acetate.The preliminary bioassay showed thatl-(2’,4,4’,5-tetramethoxybiphenyl-2-yl)propa n-2-one has anti-heart transplant rejection activity and 2,3’,4,4’-tetramethoxybiphenyl has anti-cancer activity. The results indicate that the biphenyl compounds by open ring still has the biological activities, and the group at 2 position may be requied for those activities.