19186-33-5

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Uses

Aristeromycin is an antibacterial adenosine analog.

InChI:InChI=1/C11H15N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h3-6,8-9,17-19H,1-2H2,(H2,12,13,14)/t5-,6-,8-,9+/m1/s1

Upstream product

• 5413-85-4 5-amino-4,6-dichloropyridimine 
• 78-39-7 Triethyl orthoacetate 
• 132342-52-0 ((3aR,4R,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol 
• 58462-31-0 (1R,2S,3R,5R)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol 
• 174171-97-2 (1'R,2'R,3'S,4'R)-4'-(6-aminopurin-9-yl)-1'-hydroxymethyl-2',3'-O-isopropylidenecyclopentane-2',3'-diol 
• 186540-95-4 ((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol 
• 683276-44-0 (4R,5S)-4,5-O-isopropylidenecyclopenten-1-ol 
• 698999-19-8 (3aR,6R,6aR)-2,2-dimethyl-6-vinyltetrahydro-4H-cyclopenta[d]-[1,3]-dioxol-4-one 
• 138382-27-1 (+)-(1R,4S)-1-acetoxy-4-(nitromethyl)-2-cyclopentene 
• 178456-34-3 (1R,2R)-2-acetoxy-1-(acetoxymethyl)-3-cyclopentene 
• 188118-64-1 Acetic acid (1S,4R)-4-(6-benzoylamino-purin-9-yl)-cyclopent-2-enylmethyl ester 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 16975-94-3 <1R,2S,3R,4R-(1α,2β,3β,4α)>-D-1,9-dihydro-9-<2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-6H-purin-6-one 
• 106665-46-7 N-(9-((1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl)-9H-purin-6-yl)benzamide 
• 138284-89-6 (1R,4S)-2-Amino-1,9-dihydro-9-<4-(hydroxymethyl)cyclopent-2-enyl>purin-6-one Triphosphate 
• 97336-50-0 9-[(1R,2S,3R,4R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-9H-purin-6-ylamine 
• 97336-49-7 (1S,2R,3R,5R)-5-(6-Amino-purin-9-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol 
• 118149-20-5 C₃₃H₂₆F₃N₅O₈S 
• 118149-17-0 C₃₂H₂₇N₅O₆ 
• 118188-68-4 C₃₂H₂₆FN₅O₅ 
• 110558-74-2 N-(9-((1R,3R,4S)-3-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxycyclopentyl)-9H-purin-6-yl)benzamide 
• 106665-50-3 N-(9-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-9H-purin-6-yl)benzamide 
• 264610-95-9 carbocyclic N⁶-methyl-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate) 
• 264610-92-6 N⁶-methyl-2'-O-[phenoxy(thiocarbonyl)]-3',5'-O-(tetraisopropyldisiloxa-1,3-diyl)adenosine 

Relevant academic research and scientific papers

MODIFIED CYCLIC DINUCLEOSIDE COMPOUNDS AS STING MODULATORS

Provided herein are compounds of Formula (I), Formula (II) and/or Formula (III), or pharmaceutically acceptable salts of any of the foregoing, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salt

3'3'-CYCLIC DINUCLEOTIDE ANALOGUE COMPRISING A CYCLOPENTANYL MODIFIED NUCLEOTIDE AS STING MODULATOR

The present disclosure relates to 3'3'-cyclic dinucleotides comprising a carbocyclic nucleotide and derivatives thereof, that can modulate the activity of the STING adaptor protein.

3-DEAZANEPLANOCIN DERIVATIVES

This invention describes the series of compounds based on the 3-deazaneplanocin A (DZNep) core structure designed to inhibit the function of Polycomb repressive complex 2 (PRC2) proteins.

Chiral syntheses of 6′-β-fluoroaristeromycin, 6′-β-fluoro-5′-noraristeromycin and aristeromycin

Carbocyclic nucleosides substituted at the C-6′ position are receiving increasing attention. Chiral synthetic accessibility to the biologically promising 6′-β-fluoroaristeromycin is lacking. Its preparation and that of the 5′-nor analogue are described. A

Preparation of carbocyclic S-adenosylazamethionine accompanied by a practical synthesis of (-)-aristeromycin

For the preparation of a carbocyclic nitrogen analogue of S-adenosylmethionine (carba-AdoazaMet, 4), a practical synthesis of (-)-aristeromycin (7) has been developed using variations of literature procedures. This approach called for a stereospecific synthesis of (3aR,6aR)-2,2-dimethyl-3a, 6a-dihydrocyclopenta[1,3]dioxol-4-one ((4R, 5R)-4,5-O-isopropylidene-2-cyclopentenone) (8), which was achieved by modifying reported procedures from D-(-)-ribose.

A flexible synthesis of carbanucleosides and 5′-nor-1′-homo carbanucleosides from a common precursor

Enzymatic resolution of (±)-1-acetoxy-4-(nitromethyl)-2-cyclopentene (4) provides entry into a facile 10-step route to carbanucleosides and a practical 7-step procedure to 5′-nor-1′-homo carbanucleosides. These routes are illustrated for adenine derivatives but they are adaptable to any heterocyclic base.

An expeditious route to carbocyclic nucleosides: (-)-Aristeromycin and (-)-carbodine

The readily available bicyclic lactone (-)-1 was transformed into diacetate (-)-2 which served in an expeditious route to (-)-aristeromycin (3a) and (-)-carbodine (3b) in acceptable yields.

Synthesis and incorporation of carbocyclic nucleosides into a hammerhead ribozyme domain-RNase resistance and catalytic activity

A hammerhead ribozyme domain incorporating (-)-carbodine 8a and (-)-aristeromycin 8b at selected positions, manifests increased RNase resistance and exhibits significant catalytic activity.

Biocatalytical Transformations- VI. The 4-Acetamido-cyclopent-2-ene Carboxylate Route Revisited: Synthesis of (+)- and (-)-Aristeromycin

Enantiomerically pure (+)-as well as (-)-aristeromycin can be synthesized starting from (+)- or (-)-butyl (or hexyl) 4-acetamido-cyclopent-2-ene carboxylate; these carboxylates are easily obtained from their corresponding racemates by hydrolysis with the lipase from Candida rugosa.

Highly asymmetric enzymatic hydrolysis and transesterification of meso-bis(acetoxymethyl)- and bis(hydroxymethyl)cyclopentane derivatives: An insight into the active site model of Rhizopus delemar lipase

Rhizopus delemar lipase (RDL)-catalysed hydrolysis of meso-1,3-bis(acetoxymethyl)cyclopentane derivatives (7, 12) and Pseudomonas fluorescens lipase (PFL)-catalysed hydrolysis of 7 afforded the chiral monoacetates (15, 16) of > 99% ee. In explanation of these high enantioselectivities of RDL, the simple box-type active site model of enzyme was tentatively proposed. On the other hand, PFL-catalysed transesterification of meso-bis-(hydroxymethyl)cyclopentane (6) afforded (+)-16 of > 99% ee. The obtained (+) and (-)-16 were converted into the natural carbocyclic nucleoside(-)-aristeromycin (25), respectively.