Syntheses Of Dehydroabietylamine Derivatives And Biological Activity Research

Dehydroabietylamine is one of the chemical products of rosin. While dehydroabietylamine derivatives,which have a steroid-like multicyclic diterpene structure,have been recognized that they have antibacterial,anti-virus and anti-cancer activies as sterilization etc.. The purpose of this paper is to synthesize new dehydroabietylamine derivatives that have the potential applied to anti-bacterial and anti-cancer fields, and to test the biological activity of anti-cancer and antibacterial. It is significant to develop further processing of rosin products.In this paper, starting from dehydroabietylamine,12-hydroxy-acetyl-dehydroabietylamine and 12-fluoro-acetyl-dehydroabietylamine was synthesized through by nitration, reduction and diazotization respectively. Dehydroabietylamine was treated with sulfuric acid and nitric acid then obtained 12,14-dinitro-dehydroabietylamine.There are two novel compounds. These compounds were characterized by FT-IR,1HNMR,ESI-MS etc..The paper also presents that substituted salicylaldehyde-ethanol solution and substituted pyridine-carboxaldehyde-ethanol solution were added into 12,14-dinitro-dehydroabietylamine-ethanol solution respectively and the mixture was refluxed for 3 h, then filtrated, evaporated and obtained twenty two novel Schiff bases. In addition, some novel Schiff bases-ethanol solution under heated conditions were reducted by sodium borohydride,then obtained six novel reduction products.These new compounds were characterized by FT-IR,1HNMR,ESI-MS and high-resolution mass spectrometry.These new compounds were tested the activity of anti-cancer on the liver cancer cells (HepG2) growth inhibition, the result showed that 2-hydroxy-3-methyl benzaldehyde 12,14-dinitro dehydroabietylamine Schiff base and the reduction product of 2-bromo-5-formyl pyridine 12,14-dinitro dehydroabietylamine Schiff base have good inhibiting effect on the liver cancer cells (HepG2) while have less harmful to the normal cells(L02).The preliminary test for bacteriostatic activity indicated that 3-methoxy-4-hydroxy aldehyde 12,14-dinitro dehydroabietylamine Schiff base,2-hydroxy-3-methyl benzaldehyde 12,14-dinitro dehydroabi-etylamine Schiff base,4-trifluoromethyl methoxybenzylidene 12,14-dinitro dehydroabietyla-mine Schiff base,3-fluoro-5-trifluoromethyl benzaldehyde 12,14-dinitro dehydro abietylamine Schiff Base and 3,4-difluorophenyl aldehyde 12,14-dinitro dehydroabietylamine Schiff base had strong antibacterium activity against E. coli while 3-methoxy-4-hydroxy aldehyde 12,14-dinitro dehydroabietylamine Schiff base had strong antibacterium activity against Pycnoporus cinnabarinus,2-hydroxy-3-methyl benzaldehyde 12,14-dinitro dehydroabietylamine Schiff base had strong antibacterium activity against Phanerochete chrysosporiumand and Penicillium rugulosum;2-fluoro-4-bromo aldehyde 12,14-dinitro dehydroabietylamine Schiff base had certain antibacterium activity against E. coli, Phanerochete chrysosporium and Penicillium rugulosum while 3-fluoro-5-trifluoromethyl benzaldehyde 12,14-dinitro dehydroabietylamine Schiff base had certain antibacterium activity against Pycnoporus cinnabarinus,2-hydroxy-3- methyl benzaldehyde 12,14-dinitro dehydroabietylamine Schiff base had certain antibacterium activity against staphylococci aureus and Bacillus subtilis.