5605-63-0

Basic information

• Product Name: 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE
• Synonyms: 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE
• CAS NO: 5605-63-0
• Molecular Formula: C₂₀H₂₃N₅O₆S
• Molecular Weight: 461.49152
• Mol File: 5605-63-0.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• Solubility: Chloroform
• CAS DataBase Reference: 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE(5605-63-0)
• EPA Substance Registry System: 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE(5605-63-0)

Safety Data

• Hazardous Substances Data: 5605-63-0(Hazardous Substances Data)

Usage

Uses

2'',3''-O-Isopropylidene-5''-O-tosyladenosine is an intermediate in the synthesis of Adenosine 5’-Diphosphate-13C5 Ammonium Salt Hydrate (A281697), which is the isotope labelled analog of Adenosine 5’-Diphosphate Ammonium Salt Hydrate (A281700); a nucleoside diphosphate that interacts with a family of ADP receptors found on platelets (P2Y1, P2Y12 and P2X1), to induce platelet activation. ADP in the blood is converted to adenosine by the action of ecto-ADPases, inhibiting further platelet activation via adenosine receptors.

Upstream product

• 362-75-4 2',3'-isopropylidene adenosine 
• 98-59-9 p-toluenesulfonyl chloride 
• 58-61-7 adenosine 

Downstream Products

• 53276-26-9 (S)-5’-(S)-(3-amino-3-carboxypropyl)-5’-thioadenosine 
• 34245-48-2 5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 
• 979-92-0 S-(5'-adenosyl)-L-homocysteine 
• 80860-53-3 S-methyl-N⁶,O^2'_,O3'-tris-(toluene-4-sulfonyl)-5'-thio-adenosine 
• 2457-80-9 5'-Deoxy-5'-methylthioadenosine 
• 17298-58-7 5'-S-methyl-5'-thioinosine 
• 30685-66-6 5'-iodo-5'-deoxy-2',3'-O-isopropylideneadenosine 
• 22415-88-9 9-(5-Desoxy-β-D-ribo-hexofuranosyl)adenin 
• 129828-73-5 N⁴-(5'-adenosyl)-N⁴-methyl-2-(R,S),4-diaminobutanoic acid 
• 84365-03-7 5'-S-dimethylarsino-5'-thio-2',3'-O-isopropylidene-5'-deoxyadenosine 
• 75145-82-3 5'-Desoxyinosin-5'-carbonitril 
• 59696-82-1 5'-Desoxyadenosin-5'-carbonitril 

Relevant articles and documents

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Selective inhibition of TRPM2 channel by two novel synthesized ADPR analogues

Transient receptor potential melastatin-2 (TRPM2) channel critical for monitoring internal body temperature is implicated in the pathological processes such as neurodegeneration. However, lacking selective and potent TRPM2 inhibitors impedes investigation and validation of the channel as a drug target. To discover novel and selective TRPM2 inhibitors, a series of adenosine 5′-diphosphoribose analogues were synthesized, and their activities and selectivity were evaluated. Whole-cell patch-clamp recordings were employed for screen and evaluation of synthesized compounds. Two compounds, 7i and 8a, were identified as TRPM2 inhibitors with IC50 of 5.7 and 5.4?μm, respectively. Both 7i and 8a inhibited TRPM2 current without affecting TRPM7, TRPM8, TRPV1 and TRPV3. These two TRPM2 inhibitors can serve as new pharmacological tools for further investigation and validation of TRPM2 channel as a drug target, and the summarized structure–activity relationship (SAR) may also provide insights into further improving existing inhibitors as potential lead compounds.

α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5′-Nucleotidase (CD73) Inhibitors

ecto-5′-Nucleotidase (eN, CD73) catalyzes the hydrolysis of extracellular AMP to adenosine. eN inhibitors have potential for use as cancer therapeutics. The eN inhibitor α,β-methylene-ADP (AOPCP, adenosine-5′-O-[(phosphonomethyl)phosphonic acid]) was used as a lead structure, and derivatives modified in various positions were prepared. Products were tested at rat recombinant eN. 6-(Ar)alkylamino substitution led to the largest improvement in potency. N6-Monosubstitution was superior to symmetrical N6,N6-disubstitution. The most potent inhibitors were N6-(4-chlorobenzyl)- (10l, PSB-12441, Ki 7.23 nM), N6-phenylethyl- (10h, PSB-12425, Ki 8.04 nM), and N6-benzyl-adenosine-5′-O-[(phosphonomethyl)phosphonic acid] (10g, PSB-12379, Ki 9.03 nM). Replacement of the 6-NH group in 10g by O (10q, PSB-12431) or S (10r, PSB-12553) yielded equally potent inhibitors (10q, 9.20 nM; 10r, 9.50 nM). Selected compounds investigated at the human enzyme did not show species differences; they displayed high selectivity versus other ecto-nucleotidases and ADP-activated P2Y receptors. Moreover, high metabolic stability was observed. These compounds represent the most potent eN inhibitors described to date.