54503-61-6

Basic information

• Product Name: 5-bromo-2',3'-O-isopropylideneuridine
• Synonyms: 5-bromo-2',3'-O-isopropylideneuridine;5-Bromo-2'-O,3'-O-(1-methylethylidene)uridine
• CAS NO: 54503-61-6
• Molecular Formula: C₁₂H₁₅BrN₂O₆
• Molecular Weight: 363.1613
• EINECS: 259-190-0
• Mol File: 54503-61-6.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-bromo-2',3'-O-isopropylideneuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2',3'-O-isopropylideneuridine(54503-61-6)
• EPA Substance Registry System: 5-bromo-2',3'-O-isopropylideneuridine(54503-61-6)

Safety Data

• Hazardous Substances Data: 54503-61-6(Hazardous Substances Data)

Upstream product

• 957-75-5 5-bromouridine 
• 67-64-1 acetone 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 118397-01-6 5,5-dibromo-O⁶,5'-cyclo-5,6-dihydro-2',3'-O-isopropylidineuridine 
• 118357-44-1 (5R,6S)-5-bromo-O⁶,5'-cyclo-5,6-dihydro-2'3'-O-isopropylidineuridine 
• 118397-03-8 (5S,6S)-5-bromo-O⁶,5'-cyclo-5,6-dihydro-2'3'-O-isopropylidineuridine 

Downstream Products

• 100109-57-7 6-cyano-2',3'-O-isopropylidene-5'-O-tosyluridine 
• 29428-50-0 5-<(methylcarboxy)methyl>uridine 
• 20964-06-1 5-(carboxymethyl)uridine 
• 110920-78-0 N³,5'-O-dibenzoyl-2',3'-O-isopropylideneuridine-5-malonic acid dimethyl ester 
• 110920-83-7 N³-benzoyl-N¹-(5-O-benzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)urea 
• 116431-58-4 1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-phenylsulfanyl-1H-pyrimidine-2,4-dione 
• 110522-97-9 5-phenylthiouridine 
• 57901-65-2 9,5'-cyclo-3-(β-D-ribofuranosyl)-8-azaxanthine 
• 656808-46-7 5'-O-(4-fluorobenzoyl)-2',3'-O-isopropylidene-5-bromouridine 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 116431-66-4 1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-phenylselanyl-1H-pyrimidine-2,4-dione 
• 135067-76-4 O⁶,5'-cyclo-2',3'-O-isopropylidene-5-phenylselenouridine 
• 20406-82-0 2',3'-O-isopropylidene-5-hydroxyuridine 
• 19556-62-8 6,5'-anhydro-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)barbituric acid 

Relevant articles and documents

A novel one-step method for the synthesis of C-5-substituted O 6,5′-cyclopyrimidine nucleoside analogues in ammonia water

(Chemical Equation Presented) A novel one-step method for preparing C-5-substituted O6,5′-cyclopyrimidine nucleoside analogues is reported. This method employs molecular iodine to mediate the cyclization from the 5′-O-hydroxyl group of the sugar ring and C-6 at the position of the nitrogen base in ammonia water under mild conditions without any other aprotic organic solvent.

Lys314 is a nucleophile in non-classical reactions of orotidine-5′- monophosphate decarboxylase

Orotidine-5′-monophosphate decarboxylase (OMPD) catalyzes the decarboxylation of orotidine-5′-monophosphate (OMP) to uridine-5′-monophosphate (UMP) in an extremely proficient manner. The reaction does not require any cofactors and proceeds by an unknown mechanism. In addition to decarboxylation, OMPD is able to catalyze other reactions. We show that several C6-substituted UMP derivatives undergo hydrolysis or substitution reactions that depend on a lysine residue (Lys314) in the OMPD active site. 6-Cyano-UMP is converted to UMP, and UMP derivatives with good leaving groups inhibit OMPD by a suicide mechanism in which Lys314 covalently binds to the substrate. These non-classical reactivities of human OMPD were characterized by cocrystallization and freeze-trapping experiments with wildtype OMPD and two active-site mutants by using substrate and inhibitor nucleotides. The structures show that the C6-substituents are not coplanar with the pyrimidine ring. The extent of this substrate distortion is a function of the substituent geometry. Structurebased mechanisms for the reaction of 6-substituted UMP derivatives are extracted in accordance with results from mutagenesis, mass spectrometry, and OMPD enzyme activity. The Lys314based mechanisms explain the chemodiversity of OMPD, and offer a strategy to design mechanism-based inhibitors that could be used for antineoplastic purposes for example.

ODCASE INHIBITORS FOR THE TREATMENT OF MALARIA

The present invention includes methods of treating or preventing malaria by administering an anti-malarial effective amount of 6-substituted uridine derivatives to a subject need thereof. The invention also includes new 6-substituted uridine derivatives for use as therapeutics, in particular to treat malaria.