436847-13-1

Usage

Uses

Used in Antiviral Applications:
((1R,2R,3S,5S)-4-(6-amino-2-chloro-9H-purin-9-yl)-2,3-dihydroxybicyclo[3.1.0]hexan-1-yl)methyldihydrogenphosphate is used as an antiviral agent for inhibiting the synthesis of viral DNA by targeting the viral DNA polymerase enzyme, thereby preventing the replication of the virus.
Used in Antineoplastic Applications:
((1R,2R,3S,5S)-4-(6-amino-2-chloro-9H-purin-9-yl)-2,3-dihydroxybicyclo[3.1.0]hexan-1-yl)methyldihydrogenphosphate is used as an antineoplastic agent for its cytotoxic effects on cancer cells by interfering with their DNA replication and causing cell death.
Used in Pharmaceutical Industry:
((1R,2R,3S,5S)-4-(6-amino-2-chloro-9H-purin-9-yl)-2,3-dihydroxybicyclo[3.1.0]hexan-1-yl)methyldihydrogenphosphate is used as a potential therapeutic agent for the treatment of viral infections and various types of cancer, as it is being researched for its antiviral and antineoplastic properties.

Upstream product

• 436847-27-7 (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-2-chloro-9H-purin-9-yl)-1-[(di-tert-butyl phosphate)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene) 
• 281191-63-7 (1'R,2'R,3'S,4'R,5'S)-4-(2,6-dichloropurin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene) 
• 436847-21-1 (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-2-chloro-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene) 
• 436847-23-3 (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-2-chloro-9H-purin-9-yl)-1-[hydroxymethyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene) 
• 156126-13-5 (1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol 
• 5451-40-1 2,6 dichloropurine 

Relevant academic research and scientific papers

Synthesis of ethyl (1S,2R,3S,4S,5S)-2,3-O-(isopropylidene)-4-hydroxy- bicyclo[3.1.0]hexane-carboxylate from l-ribose: A versatile chiral synthon for preparation of adenosine and P2 receptor ligands

Substitution of the ribose moiety of various nucleosides and nucleotides with the (N)-methanocarba ring system increases the potency and selectivity as ligands at certain subtypes of adenosine and P2 receptors. We have prepared a key intermediate in the synthesis of these derivatives, ethyl (1S,2R,3S,4S,5S)-2,3-O-(isopropylidene)-4-hydroxybicyclo[3.1.0] hexane-carboxylate (15), starting from L-ribose (8) as a readily available, enantiopure building block. L-ribose was converted to the corresponding 5′-iodo derivative (9), which was cleaved reductively with Zn. Improvements were made in subsequent steps corresponding to a published route to biologically important (N)-methanocarba 5′-uronamido nucleosides, and new steps were added to prepare related 5′-nucleotides. Copyright Taylor & Francis Group, LLC.

Structure-activity relationship of (N)-methanocarba phosphonate analogues of 5′-AMP as cardioprotective agents acting through a cardiac P2X receptor

P2X receptor activation protects in heart failure models. MRS2339 3, a 2-chloro-AMP derivative containing a (N)-methanocarba (bicyclo[3.1.0]hexane) system, activates this cardioprotective channel. Michaelis-Arbuzov and Wittig reactions provided phosphonate analogues of 3, expected to be stable in vivo due to the C-P bond. After chronic administration via a mini-osmotic pump (Alzet), some analogues significantly increased intact heart contractile function in calsequestrin-overexpressing mice (genetic model of heart failure) compared to vehicle-infused mice (all inactive at the vasodilatory P2Y1 receptor). Two phosphonates,(1′S,2′R,3′S,4′R,5′S)- 4′-(6-amino-2-chloropurin-9-yl)-2′,3′-(dihydroxy) -1′-(phosphonomethylene)-bicyclo[3.1.0]hexane, 4 (MRS2775), and its homologue 9 (MRS2935), both 5′-saturated, containing a 2-Cl substitution, improved echocardiography-derived fractional shortening (20.25% and 19.26%, respectively, versus 13.78% in controls), while unsaturated 5′-extended phosphonates, all 2-H analogues, and a CH3-phosphonate were inactive. Thus, chronic administration of nucleotidase-resistant phosphonates conferred a beneficial effect, likely via cardiac P2X receptor activation. Thus, we have greatly expanded the range of carbocyclic nucleotide analogues that represent potential candidates for the treatment of heart failure.

Adenine nucleotide analogues locked in a Northern methanocarba conformation: Enhanced stability and potency as P2Y1 receptor agonists

Preference for the Northern (N) ring conformation of the ribose moiety of nucleotide 5′-triphosphate agonists at P2Y1, P2Y2, P2Y4, and P2Y11 receptors, but not P2Y6 receptors, was established using a