Synthesis, Antibacterial And Antitumor Studies Of Rosin - Based Quaternary Ammonium Salts

Rosin is a kind of important natural resources in Chemical industry of forestproducts, resin acids is the main component in rosin, as its unique chemical structureand biological activity has been generally widespread attention. The main componentsof rosin was chemically modified, the important research for the synthesis of moreand higher biological activity from rosin derivatives. In this paper, rosin acids as rawmaterials,15compounds were synthesized by chemical modification,In thosecompounds,11ones were new compounds. there are Leuckart-Clarke, acylation,acidification, replace, ring opening reaction. Three categories compound was nameby NN Dehydroabietic acid dimethyl based quaternary ammonium,NNdimethylquaternary ammonium Dehydroabietylamine and rosin acid based quaternaryammonium, Respectively.Their structures were characterized by IR,1H NMR,13CNMR and Single Crystal X-ray Diffraction. The antibacterial activity and antitumoractivity of15compounds were studied.The antibacterial activity of the derivatives was estimated by the2-fold agardilution method.Gram-negative bacteria(Klebsiell apneumonia,Escheri chiacoli,Pseudomonas aeruginosa, Enterobacter aerogenes) and Gram-positive bacteria(Staphyloccocus aureu, Staphyloccocus epidermidis)were selected as test species. Theresults showed that MIC of compound2a against Pseudomonas aeruginosa、Enterobacter aerogenes、Escherichia coli and Staphyloccocus epidermidis were32μg/mL,The MIC of compound2d against Pseudomonas aeruginosa was32μg/mL,The MIC of compound3c against Klebsiella pneumonia and Staphyloccocusepidermidis was16μg/mL. MIC of compounds4a、4b and4c Against Klebsiellawere128、64、16μg/mL,the antibacterial activityof4a、4b and4c was increased byquaternary ammonium salt′s number, The results suggest that compound2a、2d and3c can be further screening of antibacterial activity.Four kinds of cancer cell (human lung cancer cell, human breast cancer cell,human hepatoma cell, and human gastric cancer cell) were selected as test cancer cell. 15compounds were estimated by the MTT method. As the IC50of compound waslower than10μg/mL, It was judged by the compound whether have effects on againsttumor cell in vitro. The results showed that2d has good antitumor activity againstfour kinds of tumor cell. The IC50of compound2dagainsthuman lung cancer cell,human breast cancer cell, human hepatoma celland human gastric cancer cell were13.95、23.77、11.43、6.78μg/mL, Compound2d showed S changes inhibition againstfour kinds of tumor cell. NN dimethyl quaternary ammoniumDehydroabietylamineshow good antitumor activity on human gastric cancer cell. The IC50of compound3eagainst human gastric cancer cell was5.84μg/mL,4a,4b and4c show weak antitumoractivity against four kinds of tumor cell.By the experiment, Compounds2a、2d and3c can be used as a furtherdevelopment of broad-spectrum antibacterial agents, compound2d can be used as afurther development of antitumor agents. the antitumor of compound2d can beevaluated by animal tumor model, it also can be showed that a comprehensiveevaluation of antitumor activity and antitumor spectrum.