Synthesis And Biological Activity Of Novel4-Hydroxyl Tryptamine

Tryptamine derivatives have a lot of physiological and pharmacological activity such asantitumor cells, inhibit melanin and antimelanoma cells, anti bacteria, the treatment of diabetesand antioxidant.Since the Hideya Saito group isolated the two compounds (compounds6and7in Table1-1) from the Safflower Seed for the first time in1978, chemistry researchers havepaid much more attentionon on its pharmacological and physiological activity.The following contents were studied in this paper mainly:1. Using4-hydroxy indole as starting material, we designed and synthesized eight kindsof4-hydroxy tryptamine derivatives, including7a(the salt of N-methyl-N-ethyl-4-hydroxyltryptamine fumarate),7b(the salt of N-methyl-N-i-propyl-4-hydroxyl tryptamine fumarate),7c(the salt of piperidyl-4-hydroxy tryptamine fumarate),7d(the salt of morpholinyl-4-hydroxyltryptamine fumarate),7e(N-methyl-N-ethyl-4-acetyl oxygen tryptamine fumarate),7f(the salt ofN-methyl-N-isopropyl-4-acetyl oxygen tryptamine fumarate),7g(the salt of piperidyl-4-macetyloxygen tryptamine fumarate) and7h(morpholinyl-4-acetyl oxygen tryptamine fumaratesalt). The precursor compounds5a and5b, of compounds7a and7b and theprecursor compounds6a and6b of compounds7e and7f had been synthesized before,compound7c,7d,7g and7h were synthesized for the first time. All of the the intermediates andtarget compounds were characterized by nuclear magnetic resonance hydrogen spectrum andcarbon spectrum.2. The synthetic problems mainly in4a~4d and5a~5d compounds were illustrated.The affecting factors of the synthesis efficiency were discussed. The method of synthesis andpurification were improved. The pros and cons of all conditiongs were considered to improvethe yield and effiency.3. The antioxidant activities of the eight target compounds were investigated by using1,1-diphenyl-2-picryl-hydrazyl radical scavenging assay (DPPH),superoxide radical scavengingassay(O2-), and hydroxyl radical scavenging assay (OH).The experiment results showed thatcompounds7a,7b,7c,7d exhibited strong activity in scaverging DPPH radical(clearance rateare85.25-90.73%)．Compared with Vc， the target compounds exhibites poor scavenging effecton OH slightly, but the overall level of each compound was the same.The clearance O2-abilityof compounds7a,7d,7g,7h (19.34,35.35,27.93and31.74, respectively) was stronger than Vc(17.58) in the same concentration.4. The structures and their biological activities were discussed.