Open Access. Powered by Scholars. Published by Universities.®

Medicinal-Pharmaceutical Chemistry Commons

Open Access. Powered by Scholars. Published by Universities.®

2010

(α-fluoro)vinyl sulfides.

Articles 1 - 1 of 1

Full-Text Articles in Medicinal-Pharmaceutical Chemistry

Developing Of Germyldesulonylation And Thiodesulfonylation Reactions For The Synthesis Of Novel Nucleoside Analogues. Efficient Synthesis Of Novel (Α-Fluoro)Vinyl Sulfides, Pablo R. Sacasa Jr Jul 2010

Developing Of Germyldesulonylation And Thiodesulfonylation Reactions For The Synthesis Of Novel Nucleoside Analogues. Efficient Synthesis Of Novel (Α-Fluoro)Vinyl Sulfides, Pablo R. Sacasa Jr

FIU Electronic Theses and Dissertations

S-adenosyl-L-homocysteine (AdoHcy) hydrolase effects hydrolytic cleavage of AdoHcy to produce both adenosine and L-homocysteine and is a feedback inhibitor of S-adenosyl-L-methionine (SAM). Nucleoside analogues bearing an alkenyl or fluoroalkenyl chain between sulfur and C5′ utilizing Negishi coupling reactions were synthesized. Palladium-catalyzed cross-coupling between the 5′-deoxy-5′-(iodomethylene) nucleosides and alkylzinc bromides gives analogues with the alkenyl unit. Palladium-catalyzed selective monoalkylation of 5′-(bromofluoromethylene)-5′-deoxy-adenosine with alkylzinc bromide afford adenosylhomocysteine analogues with a 6′-(fluoro)vinyl motif. The vinylic adenine nucleosides produced time-dependent inactivation of the S-adenosyl-L-homocysteine hydrolases. Stannydesulfonylation reaction is a critical step in the synthesis of E-fluorovinyl cytidine ...