Synthesis of 1,2-methano-tetrahydrofuran derivatives and 1´,2´-methano-2´,3´-dideoxynucleosides as potential antivirals
dc.contributor.advisor | Hanessian, Stephen | |
dc.contributor.author | Rico Duque, Jenny Lorena | |
dc.date.accessioned | 2018-05-23T15:42:44Z | |
dc.date.available | NO_RESTRICTION | fr |
dc.date.available | 2018-05-23T15:42:44Z | |
dc.date.issued | 2018-05-10 | |
dc.date.submitted | 2018-02 | |
dc.identifier.uri | http://hdl.handle.net/1866/20042 | |
dc.subject | Tin-mediated cyclopropanation | fr |
dc.subject | Nucleosides analogues | fr |
dc.subject | Phosphoramidates | fr |
dc.subject | Antiviral agents | fr |
dc.subject | 1,2-Methano-1-substituted-4-hydroxymethyl-tetrahydrofurans | fr |
dc.subject | Constrained nucleosides | fr |
dc.subject | 1´,2´-methano-2´,3´-dideoxyuridine | fr |
dc.subject | Cyclopropanation à l'étain | fr |
dc.subject | Analogues nucléosidiques | fr |
dc.subject | Phosphoramidates | fr |
dc.subject | Activité antivirale | fr |
dc.subject | 1,2-Methano-1-substituted-4-hydroxymethyl-tetrahydrofuranes | fr |
dc.subject | 1´,2´-methano-2´,3´-désoxyuridine | fr |
dc.subject | Nucléosides contraints | fr |
dc.subject.other | Chemistry - Organic / Chimie organique (UMI : 0490) | fr |
dc.title | Synthesis of 1,2-methano-tetrahydrofuran derivatives and 1´,2´-methano-2´,3´-dideoxynucleosides as potential antivirals | fr |
dc.type | Thèse ou mémoire / Thesis or Dissertation | |
etd.degree.discipline | Chimie | fr |
etd.degree.grantor | Université de Montréal | fr |
etd.degree.level | Maîtrise / Master's | fr |
etd.degree.name | M. Sc. | fr |
dcterms.abstract | En partant de la (S)-4-hydroxyméthyl-butyrolactone, commerciale et largement utilisée, la synthèse stéréocontrôlée de composés reliés de 1,2-méthano-1-substituted-4-hydroxymethyl-tétrahydrofuranes a été réalisée en utilisant une stratégie de cyclopropanation publiée par le groupe du Professeur Hanessian. Dans le cadre d'une collaboration avec le SGC de Toronto, certains 1,2-méthano-1,4-tétrahydrofuranes substitués ont été testés contre un panel d'histone-méthyl-transférases. Dans le second chapitre, une courte synthèse de trois analogues nucléosidiques contraints, 1´,2´-méthano-2´,3´-désoxypseudouridine (C-nucléoside), le 1´,2´-méthano-2´,3´-désoxyuridine et le 1´,2´-méthano-2´,3´-désoxycytidine et leur pro-médicament aryloxyphosphoramidate correspondant a été réalisée en utilisant la stratégie de cyclopropanation. Les tests biologiques de ces analogues modifiés en tant qu'agents antiviraux ont été effectués par les laboratoires Merck à Rahway, NY. USA. Aucun des composés n'a montré d'activité contre le VIH, le VRS et l'Herpès. | fr |
dcterms.abstract | Starting from the commercially available and widely used (S)-4-hydroxymethyl- butyrolactone, the stereocontrolled synthesis of bicyclic 1,2-methano-1-subtituted-4-hydroxymethyl-tetrahydrofurans was accomplished using a tin-mediated cyclopropanation strategy reported by the Hanessian group. As a part of a collaboration with the SGC of Toronto, some of the 1,2-methano-1-substituted-4-hydroxymethyl-tetrahydrofurans were tested against a panel of histone methyltransferases. In the second chapter, a short synthesis of three constrained nucleosides analogues, 1´,2´-methano-2´,3´-dideoxypseudouridine (C-nucleoside); 1´,2´-methano-2´,3´-dideoxyuridine and 1´,2´-methano-2´,3´-dideoxycytidine and their corresponding aryloxyphosphoramidate-prodrugs was achieved using the tin-mediated cyclopropanation strategy. The biological testing of the modified analogues as antiviral agents was performed by Merck in Rahway, NY, USA. None of the compounds showed activity against HIV, RSV and Herpes. | fr |
dcterms.language | eng | fr |
Files in this item
This item appears in the following Collection(s)
This document disseminated on Papyrus is the exclusive property of the copyright holders and is protected by the Copyright Act (R.S.C. 1985, c. C-42). It may be used for fair dealing and non-commercial purposes, for private study or research, criticism and review as provided by law. For any other use, written authorization from the copyright holders is required.