新型脱氢枞胺衍生物的合成及其生物活性研究

新型脱氢枞胺衍生物的合成及其生物活性研究Synthesis and biological activities of several novel derivativesof dehydroabietylamineAbstractDehydroabietic amine is one of the rosin derivatives.Its characteristic tricyclic diterpenestructure feature the molecule with antibacterial,antivirus and anticancer activities.The purposeof this paper is to modify the B ring of dehydroabietic amine,synthesize new derivatives ofdehydroabietic amine.Some of the synthesized compounds were tested the ability ofanti-cancer,and anti-free radical,anti-HIV.It is hoped that the further processing industry ofrosin can be prompted,while these rosin derived compounds are applied to biopharmaceuticalfields.Starting from dehydroabietic amine,acetyl dehydroabietic amine -7-ketone and threefluorine acetyl dehydroabietic amine -7-ketone were synthetized by acetylization and chromicacid oxidation.Then Some active groups like acetyl hydrazine,benzoyl hydrazine,semicarbazide,amino thiourea,isoniazid,carbon hydrazine and hydrochloric acid hydroxyamine were inserted to B ring by Schiff base condensation reaction.A series of new type ofdehydroabietic amine derivatives which never been reported were synthesesed.This paper also studies the further oxidation reaction to the acetyl dehydroabietic amine-7-ketone and three fluorine acetyl dehydroabietic amine-7-ketone,The reaction using aceticacid as solvent,selenium dioxide as oxidizing agents,in 80C reaction 5 hours,oxidationreaction results dehydroabietic amine six doesn't expected oxidation into ketone,but in a 5,6formed between the olefinic bond.Two new dehydroabietic amine derivatives were synthesizedby this reaction,and it produce a far-reaching significance for future research how to transformdehydroabietic amine B ring.The studu of how to combine gallic acid with dehydroabietic amine were successfullydeveloped by using new synthesis methods.First,three acetyl gallic acid were synthesized byusing acylation reaction,then use it to synthetic three acetyl gallic acid chloride.The N-(3,4,5three acetyl benzoic acid)-dehydroabietic amine were synthesized through acylation reactionby hree acetyl gallic acid chloride and dehydroabietic amine.At larst,the N-(3,4,5-threeacetyl benzoic acid)-dehydroabietic amine were hydrolyzed by using hydrazine hydrate toproduce N-(3,4,5-three hydroxy benzoic acid)-dehydroabietic amine.In addition,a new typeof dehydroabietic amine Schiff base were synthesized by dehydroabietic amine and 3,4,5-trimethoxy-Benzaldehyde.Structures of the synthesized compounds were characterized by IR,H NMR,13C NMR,0