Advanced search options

Advanced Search Options 🞨

Browse by author name (“Author name starts with…”).

Find ETDs with:

in
/  
in
/  
in
/  
in

Written in Published in Earliest date Latest date

Sorted by

Results per page:

Sorted by: relevance · author · university · dateNew search

You searched for subject:(Allyl sulfone). Showing records 1 – 2 of 2 total matches.

Search Limiters

Last 2 Years | English Only

No search limiters apply to these results.

▼ Search Limiters


University of Toronto

1. Lau, Chan Tong. Rhodium-catalyzed Addition of Arylboronic Acids to Nitriles: Application in the Synthesis of Unsymmetrical Polysubstituted Pyridines.

Degree: 2011, University of Toronto

Investigations pertaining to the rhodium(I)-catalyzed addition of arylboronic acids to (arylsulfonyl)acetonitriles were undertaken. The resulting carbon-carbon bond forming reaction has led to the efficient synthesis of novel stereoselective (Z)-β-sulfonylvinylamines, which upon acidic hydrolysis, afford useful β-keto sulfones possessing a diverse range of aryl and sulfonyl substituents. The synthetic utility of these (Z)-β-sulfonylvinylamines was subsequently explored by generating the corresponding 1-aza-allyl anion equivalents under basic conditions. This interesting anionic intermediate was then introduced to various α,β-unsaturated systems to produce a diverse array of functionalized pyridine derivatives including unsymmetrical polysubstituted pyridines.

MAST

Advisors/Committee Members: Lautens, Mark, Chemistry.

Subjects/Keywords: rhodium; nitrile; pyridine; unsymmetrical; 1-aza-allyl anion; β-keto sulfone; β-sulfonylvinylamine; 0490

Record DetailsSimilar RecordsGoogle PlusoneFacebookTwitterCiteULikeMendeleyreddit

APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Lau, C. T. (2011). Rhodium-catalyzed Addition of Arylboronic Acids to Nitriles: Application in the Synthesis of Unsymmetrical Polysubstituted Pyridines. (Masters Thesis). University of Toronto. Retrieved from http://hdl.handle.net/1807/31293

Chicago Manual of Style (16th Edition):

Lau, Chan Tong. “Rhodium-catalyzed Addition of Arylboronic Acids to Nitriles: Application in the Synthesis of Unsymmetrical Polysubstituted Pyridines.” 2011. Masters Thesis, University of Toronto. Accessed January 26, 2021. http://hdl.handle.net/1807/31293.

MLA Handbook (7th Edition):

Lau, Chan Tong. “Rhodium-catalyzed Addition of Arylboronic Acids to Nitriles: Application in the Synthesis of Unsymmetrical Polysubstituted Pyridines.” 2011. Web. 26 Jan 2021.

Vancouver:

Lau CT. Rhodium-catalyzed Addition of Arylboronic Acids to Nitriles: Application in the Synthesis of Unsymmetrical Polysubstituted Pyridines. [Internet] [Masters thesis]. University of Toronto; 2011. [cited 2021 Jan 26]. Available from: http://hdl.handle.net/1807/31293.

Council of Science Editors:

Lau CT. Rhodium-catalyzed Addition of Arylboronic Acids to Nitriles: Application in the Synthesis of Unsymmetrical Polysubstituted Pyridines. [Masters Thesis]. University of Toronto; 2011. Available from: http://hdl.handle.net/1807/31293


Georgia Tech

2. Gotz, Marion Gabriele. Design, synthesis, and evaluation of irreversible peptidyl inhibitors for clan CA and clan CD cysteine proteases.

Degree: PhD, Chemistry and Biochemistry, 2004, Georgia Tech

Cysteine proteases are a class of proteolytic enzymes, which are involved in a series of metabolic and catabolic processes, such as protein turnover, digestion, blood coagulation, apoptosis, fertilization and cell differentiation, and the immune response system. The development of novel potent and selective inhibitors for cysteine proteases has therefore gained increasing attention among medicinal chemists. In this thesis we have reported the design, synthesis, and evaluation of several peptidyl inhibitors for clan CA and clan CD cysteine proteases. We have continued the investigation of dipeptidyl vinyl sulfones as potent and selective inhibitors for dipeptidyl peptidase I (DPPI), a lysosomal cysteine protease, which is involved in the processing of intracellular proteases, such as granzymes. We have found that DPPI tolerates negatively charged amino acid residues in the P2 position with inhibition rates of 7,600 M-1s-1. Dipeptidyl vinyl sulfones with positively charged amino acid residues at the P1 position, however, do not inhibit DPPI at all. A second project focused on the epoxidation of the double bond of the vinyl sulfone moiety of the dipeptidyl vinyl sulfones. Instead of epoxidizing the double bond, we found that an isomerization had occurred. The newly formed compounds were determined to be allyl sulfones. We tested this new class of inhibitors with clan CA proteases and obtained inhibition rates of 560 M-1s-1 for Cbz-Leu-Phe-AS-Ph with calpain I. Two new classes of compounds for the clan CD protease S. mansoni legumain were designed, synthesized, and evaluated. Aza-peptidyl epoxides were found to be potent and selective inhibitors of S. mansoni legumain with IC50’s as low as 45 nM. Aza-peptide Michael acceptors were derived from the aza-peptide epoxide design and synthesized in an analogous fashion. The aza-peptide Michael acceptors inhibited S. mansoni legumain with even lower IC50’s, as low as 10 nM. However, the aza-peptide Michael acceptors react with thioalkylating agents contained in the buffer, such as DTT. The rates of degradation were determined spectroscopically, and half-lives of 3 to 20 minutes were measured. This observation gave us insights into the enzymatic mechanism and allowed us to determine the point of attack for the legumain active site cysteine thiol. Advisors/Committee Members: Dr. James C. Powers (Committee Chair), Dr. Donald Doyle, Dr. Nicholas Hud, Dr. Niren Murthy, and Dr. Suzanne Shuker (Committee Members).

Subjects/Keywords: Allyl sulfone; Aza-peptide; Biosynthesis; Cysteine protease; Cysteine proteinases; Irreversible inhibitors; Protease inhibitors; Sulphones; Vinyl sulfone

Record DetailsSimilar RecordsGoogle PlusoneFacebookTwitterCiteULikeMendeleyreddit

APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Gotz, M. G. (2004). Design, synthesis, and evaluation of irreversible peptidyl inhibitors for clan CA and clan CD cysteine proteases. (Doctoral Dissertation). Georgia Tech. Retrieved from http://hdl.handle.net/1853/8072

Chicago Manual of Style (16th Edition):

Gotz, Marion Gabriele. “Design, synthesis, and evaluation of irreversible peptidyl inhibitors for clan CA and clan CD cysteine proteases.” 2004. Doctoral Dissertation, Georgia Tech. Accessed January 26, 2021. http://hdl.handle.net/1853/8072.

MLA Handbook (7th Edition):

Gotz, Marion Gabriele. “Design, synthesis, and evaluation of irreversible peptidyl inhibitors for clan CA and clan CD cysteine proteases.” 2004. Web. 26 Jan 2021.

Vancouver:

Gotz MG. Design, synthesis, and evaluation of irreversible peptidyl inhibitors for clan CA and clan CD cysteine proteases. [Internet] [Doctoral dissertation]. Georgia Tech; 2004. [cited 2021 Jan 26]. Available from: http://hdl.handle.net/1853/8072.

Council of Science Editors:

Gotz MG. Design, synthesis, and evaluation of irreversible peptidyl inhibitors for clan CA and clan CD cysteine proteases. [Doctoral Dissertation]. Georgia Tech; 2004. Available from: http://hdl.handle.net/1853/8072

.