Synthesis And Bioactivities Evaluation Of Naphthoquinonofuran (Thiophene) Diones And 3-acylindolizines

As an important class of nature product,naphthoquinone is used extensively in medicine and dyes,etc.In this dissertation,three series of new heterocyclic compounds were synthesized promoted by basic organic small molecule inducer.The anticancer and antibacterial activities of products were tested which laid the foundation for their application in anti-tumor new drug development in the further.The dissertation is divided into four chapters:In the first chapter,we introduced the main synthesis methods of naphthoquinone derivatives and put forward the basis,significance and innovation of this thesis.In the second chapter,the reaction of 2-hydroxy-1,4-naphthoquinone and ketene was catalyzed by NIS cooperated DABCO efficiently to give a series of naphthoquino[2,3-b]furan-4,9-diones.The structure of all products was characterized by nuclear magnetic resonance spectroscopy and high resolution mass spectrometry.The results of their anti-cancer activity indicated that nine compound(3a?3b?3c?3l?3p?3s?7a?7b?7e)had high cytotoxicity on both non-small cell lung cancer cells(A549)and three positive breast cancer cells(MCF-7).In the third chapter,a series of naphthoquinone[2,3-b]thiophenes were obtained by the reaction of unsaturated ketones,1,4-naphthoquinone and sodium sulfide hydrate catalyzed by DABCO.The structure of all products was characterized by nuclear magnetic resonance spectroscopy and high resolution mass spectrometry.The anticancer and antibacterial activities of products were tested.One compound was found to have high cytotoxicity on non-small cell lung cancer cells(A549)and three positive breast cancer cells(MCF-7).In the fourth chapter,an effective method for the synthesis of indolizines was explored by the reaction of substituted pyridine,bromide and maleic anhydride promoted by TEMPO oxidation in the presence of K2CO3 under nitrogen.It provides a new synthetic pathway for the synthesis of 3-acylindolizine.The structure of all products was characterized by nuclear magnetic resonance spectroscopy and high resolution mass spectrometry.The anticancer and antibacterial activities of all products were studied.Unfortunately,no one showed anti-cancer and antibacterial activity.