Change search
ReferencesLink to record
Permanent link

Direct link
Synthesis of novel 1.10-phenanthrolins and cyclic analogs, a potential anticancer and antimalarial agents
KTH, School of Chemical Science and Engineering (CHE).
2011 (English)Independent thesis Advanced level (degree of Master (Two Years)), 20 credits / 30 HE creditsStudent thesisAlternative title
Syntes av 1.10-fenantroliner och cykliska analoger; potentiella anticancer och antimalaria substanser (Swedish)
Abstract [en]

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.

Abstract [sv]

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.

Place, publisher, year, edition, pages
2011. , 27 p.
Keyword [en]
Phenanthroline, Antimalaria, Anticancer, TDAE [Tetrakis(dimethylamine)ethylene], Singel electron transfer
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-32945OAI: oai:DiVA.org:kth-32945DiVA: diva2:413090
Subject / course
Organic Chemistry
Educational program
Master of Science in Engineering
Uppsok
Physics, Chemistry, Mathematics
Supervisors
Examiners
Available from: 2011-04-27 Created: 2011-04-27 Last updated: 2011-05-27

Open Access in DiVA

fulltext(1347 kB)321 downloads
File information
File name FULLTEXT01.pdfFile size 1347 kBChecksum SHA-512
976a82b55d566b8c5eba388b5d3b60d75193c7e8b1cfe6ccf14f9b43d5d3da333c46fcb5a1d0a9d0661f2d0d7a6f690b8f00b16cc26018ff03d7530ca7d8425f
Type fulltextMimetype application/pdf

By organisation
School of Chemical Science and Engineering (CHE)
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar
Total: 321 downloads
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Total: 117 hits
ReferencesLink to record
Permanent link

Direct link