The Conversion of Hemiacetals into Antiviral and Anticancer Compounds

<img class="wp-block-coblocks-author__avatar-img" src="" alt="<strong>Kekeli Logoh</strong>
Kekeli Logoh

Kekeli Logoh is a rising junior (‘23) who is double majoring in Molecular Biology & Biochemistry and the College of Integrative sciences (CIS). She is also minoring in Integrative Design, Engineering, & Applied Science (IDEAS).  Kekeli is originally from Togo, but has lived in Ambler, Pennsylvania for a majority of her life. She graduated from Hatboro-Horsham High School. Kekeli’s passions include cooking, going on adventures, and binge watching shows. She is involved in WildWes, WesCF, KDC, and Habitat for Humanity.

Abstract: There is a demonstrated need for drugs targeting diseases, such as the flu, polio, and hepatitis A, caused by the Picornaviridae family. It has been established that natural and synthetic benzofuran derivatives have effective antimicrobial, antitumor, and analgesic activities. Namely, benzo[b]indeno[2,1-d]furanone, a benzofuran, exhibits effective inhibition against picornavirus at nanomolar concentrations and also has low cytotoxicity towards host cells. A report from Kim et al. constructed a novel picornavirus inhibitor that is a small, stereochemical complex benzofuroid. To make this biologically active compound, we have developed a pathway using a catalytic asymmetric addition Interrupted Feist- Bѐnary (IFB) reaction that would selectively set the stereochemistry of the final target. IFB reactions usually create racemic mixtures, however, only one enantiomer is functional.  The modified catalytic IFB reaction involves enantioselective reactions between 1,2,3-indanetrones and substituted phenols catalyzed by bis(cinchona-alkaloid)pyrimidine catalysts. This stoichiometric acid addition yields chiral cyclic hemiacetals that we should be able to convert into the benzofuranoid antiviral discussed above. In the newly developed modified catalytic IFB reaction, the final chiral cyclic hemiacetal has three possible configurations, producing six isomers in our final product. Exposure to acids causes hemiacetal products to rearrange into different conformations. Our goal is to isolate each configuration, and then convert them into the antiviral compound by reducing out one oxygen and converting the hemiacetal into an amine.


Kekeli Logoh (Chemistry Department)

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