Synthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agents
The potential antimalarial and anticancer effect of molecules containing 1,10-phenanthroline skeleton has been suspected on several previous studies. It is why the goal of this project is to synthesize novel 1,10-phenanthrolines and cyclic analogs. The originality of this project is the synthesis wa...
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KTH, Skolan för kemivetenskap (CHE)
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ndltd-UPSALLA1-oai-DiVA.org-kth-329452013-01-08T13:30:31ZSynthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agentsengSyntes av 1.10-fenantroliner och cykliska analoger; potentiella anticancer och antimalaria substanserFouilland, LauraKTH, Skolan för kemivetenskap (CHE)2011PhenanthrolineAntimalariaAnticancerTDAE [Tetrakis(dimethylamine)ethylene]Singel electron transferOrganic chemistryOrganisk kemiThe potential antimalarial and anticancer effect of molecules containing 1,10-phenanthroline skeleton has been suspected on several previous studies. It is why the goal of this project is to synthesize novel 1,10-phenanthrolines and cyclic analogs. The originality of this project is the synthesis way of these novel compounds. Indeed, these structures will be obtained through an original redox approach developed in the SMITH laboratory using the tetrakis(dimethylamino)ethylene (TDAE) reagent. The TDAE is an electron rich organic molecule which is an effective reducing agent capable of generating an anion from halogenated derivatives under mild conditions via a single electron transfer (SET). From the different substrate we will work with, the TDAE will generate an anion which will be additioned on the 1,10-phenanthroline-5,6-dione. These different substrates will be aromatic and heterocyclic nitro-benzylic, and quinonic derivates as well as bromodifluoromethyl heteroarylated substrates. A one pot two step (reduction, dehydration) reaction will be done on these addition products, in order to obtain a cyclised product. It is the first time we try these reactions on these kind on molecules, it is why this project needs a lot of optimization and that the yield obtained are medium or equal to zero. However, we observed that the addition reaction with TDAE worked with 4 substrates out of 6. We tried the cyclisation reaction on only one addition product and we think that after some improvement of the reaction conditions and the work-up, we will be able to obtain the product with a good yield. Tidigare studier har indikerat att molekyler med 1,10-phenanthrolineskelett har en skyddande effekt mot malaria och cancer. Syftet med detta projekt är att syntetisera nya 1,10-phenanthrolinar och cykliska analoger. Framställningsmetoden som användes i denna studie har inte undersökts tidigare. Föreningen skapades genom en originalmetod utnyttjande en redoxreaktion med hjälp av en TDAE-reagens. TDAE är en elektronrik organisk molekyl och fungerar som en effektiv reduktionsagent. Med hjälp av en enelektronöverföring (SET) kan en anjon framställas under milda förhållanden utifrån halogena derivat. Anjonen tillförs 1,10-phenanthroline-5,6-dione. De olika substraten är heteroaromatiska nitro-benzyliska och quinoniska derivat, samt bromodifluorometylheteroarylerade. Cykliska produkter erhölls genom en tvåstegsreaktion (reduktion, dehydratisering) genomförd i ett enda reaktionskärl. Med detta projekt har dessa reaktioner för första gången testats på den här typen av molekyler. Det krävs mer optimering eftersom utbytena var låga till medelhöga. Utav sex möjliga substrat fungerade additionsreaktionen med TDAE med fyra stycken. I detta försök testades dock endast en cyklisk reaktion på additionsprodukten. Med ytterligare förbättringar av reaktionsvillkor och upparbetningar förväntas man kunna producera önskad produkt i gott utbyte. Student thesisinfo:eu-repo/semantics/bachelorThesistexthttp://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-32945application/pdfinfo:eu-repo/semantics/openAccess |
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English |
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Others
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Phenanthroline Antimalaria Anticancer TDAE [Tetrakis(dimethylamine)ethylene] Singel electron transfer Organic chemistry Organisk kemi |
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Phenanthroline Antimalaria Anticancer TDAE [Tetrakis(dimethylamine)ethylene] Singel electron transfer Organic chemistry Organisk kemi Fouilland, Laura Synthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agents |
description |
The potential antimalarial and anticancer effect of molecules containing 1,10-phenanthroline skeleton has been suspected on several previous studies. It is why the goal of this project is to synthesize novel 1,10-phenanthrolines and cyclic analogs. The originality of this project is the synthesis way of these novel compounds. Indeed, these structures will be obtained through an original redox approach developed in the SMITH laboratory using the tetrakis(dimethylamino)ethylene (TDAE) reagent. The TDAE is an electron rich organic molecule which is an effective reducing agent capable of generating an anion from halogenated derivatives under mild conditions via a single electron transfer (SET). From the different substrate we will work with, the TDAE will generate an anion which will be additioned on the 1,10-phenanthroline-5,6-dione. These different substrates will be aromatic and heterocyclic nitro-benzylic, and quinonic derivates as well as bromodifluoromethyl heteroarylated substrates. A one pot two step (reduction, dehydration) reaction will be done on these addition products, in order to obtain a cyclised product. It is the first time we try these reactions on these kind on molecules, it is why this project needs a lot of optimization and that the yield obtained are medium or equal to zero. However, we observed that the addition reaction with TDAE worked with 4 substrates out of 6. We tried the cyclisation reaction on only one addition product and we think that after some improvement of the reaction conditions and the work-up, we will be able to obtain the product with a good yield. === Tidigare studier har indikerat att molekyler med 1,10-phenanthrolineskelett har en skyddande effekt mot malaria och cancer. Syftet med detta projekt är att syntetisera nya 1,10-phenanthrolinar och cykliska analoger. Framställningsmetoden som användes i denna studie har inte undersökts tidigare. Föreningen skapades genom en originalmetod utnyttjande en redoxreaktion med hjälp av en TDAE-reagens. TDAE är en elektronrik organisk molekyl och fungerar som en effektiv reduktionsagent. Med hjälp av en enelektronöverföring (SET) kan en anjon framställas under milda förhållanden utifrån halogena derivat. Anjonen tillförs 1,10-phenanthroline-5,6-dione. De olika substraten är heteroaromatiska nitro-benzyliska och quinoniska derivat, samt bromodifluorometylheteroarylerade. Cykliska produkter erhölls genom en tvåstegsreaktion (reduktion, dehydratisering) genomförd i ett enda reaktionskärl. Med detta projekt har dessa reaktioner för första gången testats på den här typen av molekyler. Det krävs mer optimering eftersom utbytena var låga till medelhöga. Utav sex möjliga substrat fungerade additionsreaktionen med TDAE med fyra stycken. I detta försök testades dock endast en cyklisk reaktion på additionsprodukten. Med ytterligare förbättringar av reaktionsvillkor och upparbetningar förväntas man kunna producera önskad produkt i gott utbyte. |
author |
Fouilland, Laura |
author_facet |
Fouilland, Laura |
author_sort |
Fouilland, Laura |
title |
Synthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agents |
title_short |
Synthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agents |
title_full |
Synthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agents |
title_fullStr |
Synthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agents |
title_full_unstemmed |
Synthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agents |
title_sort |
synthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agents |
publisher |
KTH, Skolan för kemivetenskap (CHE) |
publishDate |
2011 |
url |
http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-32945 |
work_keys_str_mv |
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_version_ |
1716522126949744640 |