자료유형  

 학위논문

Control Number  

0017161469

International Standard Book Number  

9798383137123

Dewey Decimal Classification Number  

547

Main Entry-Personal Name  

Cardenas, Mariel Manaloto.

Publication, Distribution, etc. (Imprint  

[S.l.] : University of California, San Diego., 2024

Publication, Distribution, etc. (Imprint  

Ann Arbor : ProQuest Dissertations & Theses, 2024

Physical Description  

604 p.

General Note  

Source: Dissertations Abstracts International, Volume: 85-12, Section: B.

General Note  

Advisor: Gustafson, Jeffrey.

Dissertation Note  

Thesis (Ph.D.)--University of California, San Diego, 2024.

Summary, Etc.  

요약Atropisomerism (or axial chirality) arises from restricted bond rotation most typically in a Csp2-Csp2 σ bonds, wherein the neighboring substitutions across the atropisomeric bond contribute energy differences through steric strain. Also referred to as axial chirality, stable atropisomerism (i.e., creating significant steric strain across the bond to give rise to two isolable enantiomers) can be very challenging to achieve. However, in stabilizing the atropisomeric axis this leads to two unique compounds that have been shown to possess profound activities in many areas of research. Within the last decade, the Gustafson group at San Diego State University has since focused on leveraging atropisomerism on its importance to drug discovery with emphasis of exploring Nheterocyclic pharmaceutically relevant scaffolds. Along with challenges to achieving stable atropisomerism within a compound, it is very often equally difficult to then furnish enantiopure atropisomers. Traditional resolution methods such as chiral separation can be inconducive in time and resources and sometimes impractical for scaffold exploration.To address this bottleneck, the Gustafson group began a marital chemistry program in developing new chemical reactions that expedite access to these atropisomeric compounds (Chapter 1). Currently, we have several atroposelective synthetic strategies via nucleophilic aromatic substitutions (SNAr, Chapter 2) which have successfully furnished atropisomeric 3- arylpyrrolopyrimidines and 3-arylquinolines. Post-functionalization from the atroposelective SNAr methods have also potentially are useful to synthesize chemical probes (Chapter 3). Furthermore, nucleophilic substitutions outside of SNAr have also been widely used for the synthesis of pharmaceutically relevant compounds (Chapter 4, vicarious nucleophilic substitution (VNS) and atroposelective alkylation by acid-catalyzed directed 'nucleophilic radicals' (Minisci chemistry)). We believe our research will impact the current need for atroposelective nucleophilic substitution strategies towards pharmaceutically relevant scaffolds in the field of asymmetric catalysis. Lastly, we shared that these chemistries furnished enantioenriched pharmaceutically relevant scaffolds in desired yields that would be useful to ongoing medicinal chemistry efforts.

Subject Added Entry-Topical Term  

Organic chemistry.

Subject Added Entry-Topical Term  

Chemistry.

Subject Added Entry-Topical Term  

Biochemistry.

Index Term-Uncontrolled  

Atropisomerism

Index Term-Uncontrolled  

Drug discovery

Index Term-Uncontrolled  

Chiral separation

Index Term-Uncontrolled  

Atropisomeric compounds

Added Entry-Corporate Name  

University of California, San Diego Chemistry (Joint Doctoral with SDSU)

Host Item Entry  

Dissertations Abstracts International. 85-12B.

Electronic Location and Access  

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Control Number  

joongbu:658017