Sustainable preparation of biphenyles structures for health applications

Job title:

Sustainable preparation of biphenyles structures for health applications

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Job description

Offer DescriptionSummaryThe preparation of (poly)aromatics from renewable resources can be performed by exploiting plateform compounds issued from the biomass such as the furfural derivatives. The recent work in the laboratory have demonstrated the possibility to convert furfural into functional benzene or pyridine rings. The proposed thesis project is the preparation of fused or sequential polyaromatic systems from our previous work by extending the available resources to other derivatives such as phenols issued from lignin or natural flavors. The final compounds obtained will be evaluated in immune-oncology with external collaborations.ContextThe synthesis of biphenyles is currently based of petrochemicals. An alternative sustainable approach will give a renewable aspect to these syntheses. From compounds issued from the biomass such as the furanic derivatives a strategy is proposed to realize this sustainable transition. The methods found in the literature are using almost only oxygenated furans. A major goal of this project is to transpose the current methods for oxygenated furans to nitrogen-containing ones. The presence of the nitrogen atoms greatly modify the activity of the catalysts used for these transformations. The experimental conditions used for oxygenated furans may not work for nitrogen-containing ones. The aim of this work is thus to find methods working on any type of furan derivatives and on more complex molecules as well that will find application in immuno-oncology.DescriptionThe structures to prepare have a biphenyle group which plays a critical role in the interaction with the target protein implied in the studied mechanism: escape of tumors from the immune response. On these biphenyles groups will be added various functionalities supposed to strengthen the interactions with the target. The project will have a synthetic part devoted to the preparation of these biphenyles and another part devoted to the sustainable preparation of the additional functionalities. The two parts will then be assembled to obtain the final compounds to be tested.MethodologyThe preparation of biphenyles will be made from furanic derivatives. A Diels-Alder reaction between the furanes and reactive dienophiles will give a cycloaddition product whose subsequent aromatization will afford aromatics. Several strategies based on this general idea will be evaluated to obtain these biphenyles, such as the conversion of bio sourced phenols into arylalkynes through a Sonogashira reaction. Those arylalkynes will give Diels-Alder cycloaddition compounds aromatized to biphenyle. The functional groups to add will also be produced by sustainable methods from furfural converted to 1,3 dipoles suitable for a reaction with alkynes or alkenes. The dipolarophile cycloaddition allows for the introduction of chemical diversity to improve the pharmacokinetic profile of the final compounds. These groups may modulate the bioavailability of the biphenyl-based compounds or the selectivity for the target proteins.RequirementsResearch Field Chemistry » Organic chemistry Education Level Master Degree or equivalentSkills/QualificationsThe applicant must have a master degree. The applicant should have a good level in either organic synthesis of catalysis, ideally knowledge in these two domains. A real motivation for the multi-step synthesis and the development of methodology in organic synthesis is critical. The expected knowledge also required is: methods for separation (flash chromatography manual or automated), practice of analytical methods (software’s for HPLC, NMR, IR…), ability to treat and interpret the data and to synthesize the obtained results, writing reports, bibliographical search. The project is associated with a possible intra-European mobility so the applicant should not be reluctant to move in other countries and must have a good level in at least scientific English.Languages FRENCH Level GoodResearch Field Chemistry » Organic chemistry Years of Research Experience NoneAdditional InformationWork Location(s)Number of offers available 1 Company/Institute IC2MP Country France State/Province Vienne City Poitiers Postal Code 86073 Street 4 rue Michel Brunet GeofieldWhere to apply E-mailphilippe.bertrand@univ-poitiers.frContact State/ProvinceVienne CityPoitiers WebsiteStreet4 rue Michel Brunet Postal Code86073 E-Mailphilippe.bertrand@univ-poitiers.fr Phone0549454085STATUS: EXPIRED

Expected salary

Location

Poitiers, Vienne

Job date

Sun, 14 Apr 2024 06:15:08 GMT

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