Rigid 3D scaffolds by a diversity-generating functional-structural-skeletal elaboration approach

Gini, Elena Claudia ORCID: 0000-0002-8971-3124 (2023). Rigid 3D scaffolds by a diversity-generating functional-structural-skeletal elaboration approach. University of Birmingham. Ph.D.

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This thesis describes the development of novel three-dimensional, heterocyclic organic scaffolds, and their derivatization to new C(sp\(^{3}\))-rich compounds as the basis for library generation. An eight step synthetic route from 4-tetrahydropyranone or N-protected 4-piperidone to α,β-conjugate carbonyl intermediates is detailed. Optimization studies and large scale syntheses routes have been developed. Five novel scaffolds were achieved through functional, structural and skeletal rearrangement of enone intermediates to generate \(\textit{in-silico}\) compound libraries. From these, a total of 1068 compounds were selected following chemical novelty, diversity and druglikeliness principles. Sixty-six compounds were selected from the \(\textit{in-silico}\) library to synthesise and characterise.

Eventually, the achieved experimental libraries were analysed for lipophilicity, hERG interaction and biological activity towards a range of targets.

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
Davies, PaulUNSPECIFIEDorcid.org/0000-0002-0340-2414
Licence: All rights reserved
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: European Commission
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
URI: http://etheses.bham.ac.uk/id/eprint/13740


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