16754-83-9

Basic information

• Product Name: 7-deazanebularin
• Synonyms: 7-deazanebularin
• CAS NO: 16754-83-9
• Molecular Formula: C11H13N3O4
• Molecular Weight: 251.23862
• Mol File: 16754-83-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 567°Cat760mmHg
• Flash Point: 296.7°C
• Appearance: /
• Density: 1.75g/cm³
• Vapor Pressure: 1.08E-13mmHg at 25°C
• Refractive Index: 1.774
• PKA: 12.46±0.70(Predicted)
• CAS DataBase Reference: 7-deazanebularin(CAS DataBase Reference)
• NIST Chemistry Reference: 7-deazanebularin(16754-83-9)
• EPA Substance Registry System: 7-deazanebularin(16754-83-9)

Safety Data

• Hazardous Substances Data: 16754-83-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13N3O4/c15-4-7-8(16)9(17)11(18-7)14-2-1-6-3-12-5-13-10(6)14/h1-3,5,7-9,11,15-17H,4H2

Upstream product

• 57024-71-2 tri-O-acetyl-1-pyrrolo[2,3-d]pyrimidin-7-yl-β-D-1-deoxy-ribofuranose 
• 69-33-0 tubercidin 
• 60343-84-2 2',3',5'-tri-O-acetyltubercidin 
• 29914-75-8 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 87791-35-3 7-(2,3,5-Tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 
• 31598-80-8 2,3,5-Tri-O-benzyl-1-O-(p-nitrobenzoyl)-β-D-arabinofuranose 
• 52492-40-7 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl bromide 
• 87791-33-1 4-Methylthio-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin 

Downstream Products

• 57024-74-5 5-iodo-N7-(β-D–ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

6-Methyl-7-Aryl-7-Deazapurine Nucleosides as Anti-Trypanosoma cruzi Agents: Structure-Activity Relationship and in vivo Efficacy

Chagas disease is a tropical infectious disease resulting in progressive organ-damage and currently lacks efficient treatment and vaccine options. The causative pathogen, Trypanosoma cruzi, requires uptake and processing of preformed purines from the host because it cannot synthesize these de novo, instigating the evaluation of modified purine nucleosides as potential trypanocides. By modifying the pyrimidine part of a previously identified 7-aryl-7-deazapurine nucleoside, we found that substitution of a 6-methyl for a 6-amino group allows retaining T. cruzi amastigote growth inhibitory activity but confers improved selectivity towards mammalian cells. By keeping the 6-methyl group unaltered, and introducing different 7-aryl groups, we identified several analogues with sub-micromolar antitrypanosomal activity. The 7-(4-chlorophenyl) analogue 14, which was stable in microsomes, was evaluated in an acute mouse model. Oral administration of 25 mg/kg b.i.d. suppressed peak parasitemia and protected mice from infection-related mortality, gave similar reductions as the reference drug of blood parasite loads determined by qPCR, but as benznidazole failed to induce sterile cure in the short time period of drug exposure (5 days).

ara-7-Deazanebularine - Synthesis of a Fluorescent Pyrrolopyrimidine Nucleoside by Phase-Transfer Glycosylation

ara-7-Deazanebularine (2b) and its 6-methylthio derivative 2a have been synthesized via phase-transfer glycosylation of 4-methylthio-7H-pyrrolopyrimidine (4a) with 1-bromo-2,3,5-tri-O-benzyl-D-arabinofuranose (7).Omitting the halogenose and carrying out the reaction of 4a or 4b in dichloromethane leads to the methylene-bridged chromophores 6a and 6b, respectively.In contrast to pyrrolopyrimidines with substituents in position 2 and 4 compound 4a is glycosylated at N-7 and N-1.The formation of anomers and isomers is influenced by the phase-transfer catalyst.The N-1glycosylated 10 is sensitive against hydrolysis at the N-glycosylic bond which is not found for the N-7 isomer 8a.Debenzylation of the methylthio nucleosides 8a or 9a is accomplished using boron trichloride.Raney nickel catalyst removes the sulfur yielding the title compound 2b which exhibits strong fluorescence.