5605-63-0

Usage

Uses

Used in Pharmaceutical Synthesis:
2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE is used as an intermediate in the synthesis of Adenosine 5’-Diphosphate-13C5 Ammonium Salt Hydrate (A281697), which is an isotope-labelled analog of Adenosine 5’-Diphosphate Ammonium Salt Hydrate (A281700). This analog is a nucleoside diphosphate that interacts with a family of ADP receptors found on platelets, such as P2Y1, P2Y12, and P2X1, to induce platelet activation. 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE is essential in the development of drugs targeting platelet activation and blood clotting disorders.
Used in Diagnostic Applications:
In the field of diagnostics, 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE is used as a key compound in the synthesis of isotope-labelled adenosine analogs. These labeled compounds can be utilized in various diagnostic techniques, such as magnetic resonance imaging (MRI) and positron emission tomography (PET), to study adenosine receptor interactions and monitor platelet activation in vivo. This helps in the early detection and monitoring of blood clotting disorders and other related conditions.
Used in Research and Development:
2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE is also used in research and development for the study of adenosine receptor biology and its role in various physiological processes. 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE can be employed in the design and synthesis of novel adenosine receptor agonists and antagonists, which can potentially lead to the development of new therapeutic strategies for treating conditions related to adenosine receptor dysregulation, such as cardiovascular diseases, neurodegenerative disorders, and inflammatory conditions.

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 
• 84365-04-8 5'-acetylthio-5'-deoxy-2',3'-O-isopropylidene adenosine 
• 131070-44-5 9-{(3aR,4R,6R,6aR)-2,2-Dimethyl-6-[4-((1Z,4Z,9Z,15Z)-10,15,20-tri-p-tolyl-porphyrin-5-yl)-phenoxymethyl]-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine 
• 34245-49-3 5'-deoxy-5'-methylamino-2',3'-O,O-(1-methylethylidene)adenosine 
• 72525-43-0 5'-O-(p-toluenesulfonyl)-2',3'-O'-isopropylideneadenosine N¹-oxide 
• 17044-80-3 3,5'-cyclo-2',3'-O-isopripylideneadenosine p-toluenesulfonate 
• 34245-48-2 5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 
• 21950-36-7 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine 
• 173097-77-3 5'-deoxy-N6-<2-(4-nitrophenyl)ethoxycarbonyl>-5'-<<2-(4-nitrophenyl)ethoxycarbonyl>amino>adenosine 
• 173097-78-4 5'-deoxy-5'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 173097-76-2 5'-deoxy-2',3'-O-isopropylidene-N6-<2-(4-nitrophenyl)ethoxycarbonyl>-5'-<<2-(4-nitrophenyl)ethoxycarbonyl>amino>adenosine 
• 173097-75-1 5'-deoxy-5'-(hexadecanoylamino)-2',3'-O-isopropylidene-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 173097-79-5 3'-O-<(tert-butyl)dimethylsilyl>-5'-deoxy-N6-<2-(4-nitrophenyl)ethoxycarbonyl>-5'-<<2-(4-nitrophenyl)ethoxycarbonyl>amino>adenosine 

Relevant academic research and scientific papers

Adenosine diphosphate ribose compound, preparation method and biological activity thereof

The invention discloses an adenosine diphosphate ribose compound, which has a general formula shown as (I), wherein the definitions of all substituents are detailed in the specification. In addition,the invention also discloses a preparation method and application of the compound. The adenosine diphosphate ribose (ADPR) structural analogue provided by the invention has specific TRPM2 (transient receptor potential melastatin 2) inhibitory activity.

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.

Improved Synthesis of MDL 73811 - A Potent AdoMetDC Inhibitor and Anti-Trypanosomal Compound

An improved synthesis of MDL 73811 - a potent AdoMetDC (S-adenosylmethionine decarboxylase) inhibitor and anti-trypanosomal compound with in vivo activity - has been completed in four steps from commercially available 2′,3′-O-isopropylideneadenosine. Util

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.

IMMUNOASSAY OF S-ADENOSYLMETHIONINE USING ANALOGS THEREOF AND PERSONALIZED THERAPEUTICS

A method of detecting the presence or absence of a disease in a patient wherein said disease is accompanied by deficient levels of S-adenosylmethionine comprising: identifying a patient that is suspected of having said disease or is at risk of having said

Bisubstrate analogue inhibitors of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase: New design with improved properties

6-Hydroxymethyl-7,8-dihydropterin pyrophosphokinase (HPPK), a key enzyme in the folate biosynthetic pathway, catalyzes the pyrophosphoryl transfer from ATP to 6-hydroxymethyl-7,8-dihydropterin. The enzyme is essential for microorganisms, is absent from humans, and is not the target for any existing antibiotics. Therefore, HPPK is an attractive target for developing novel antimicrobial agents. Previously, we characterized the reaction trajectory of HPPK-catalyzed pyrophosphoryl transfer and synthesized a series of bisubstrate analog inhibitors of the enzyme by linking 6-hydroxymethylpterin to adenosine through 2, 3, or 4 phosphate groups. Here, we report a new generation of bisubstrate analog inhibitors. To improve protein binding and linker properties of such inhibitors, we have replaced the pterin moiety with 7,7-dimethyl-7,8- dihydropterin and the phosphate bridge with a piperidine linked thioether. We have synthesized the new inhibitors, measured their Kd and IC 50 values, determined their crystal structures in complex with HPPK, and established their structure-activity relationship. 6-Carboxylic acid ethyl ester-7,7-dimethyl-7,8-dihydropterin, a novel intermediate that we developed recently for easy derivatization at position 6 of 7,7-dimethyl-7,8- dihydropterin, offers a much high yield for the synthesis of bisubstrate analogs than that of previously established procedure.

NOVEL ANTIBACTERIAL COMPOUNDS

The present invention relates to compounds of formula (I): wherein Rj, R2, R3, R4, Xi, X2, X3 and Z are as defined in claim 1. The compounds are useful in the prevention and/or treatment of bacterial infections.

LINKED PURINE PTERIN HPPK INHIBITORS USEFUL AS ANTIBACTERIAL AGENTS

The disclosure provides linked purine pterin compounds and analogues thereof that are novel HPPK inhibitors. The HPPK inhibitors described herein are compounds and the pharmaceutically acceptable salts thereof of general Formula I: (I). The variables, e.g. A1 to A3, R1 to R4, L1, L2, B1, and B2 are described herein. Compounds and salts of Formula I bind to HPPK with high affinity and specificity. Pharmaceutical compositions containing an HPPK inhibitor of Formula I and methods of treating a bacterial infection in a patient by providing one or more HPPK inhibitors of Formula I to the patient are also provided. Processes and intermediates useful for preparing compounds of Formula I are also provided. Methods of using the disclosed compounds to guide the development of additional novel anti-bacterial agents are also provided.

Antibody to 5' -Deoxy-5' - Methylthioadenosine And Uses Thereof

The present invention provides a new immunogen, a novel antibody having high specificity for MTA (5′-deoxy-5′-methylthioadenosine), methods of treatment and medicaments prepared using said antibody, and sensitive assays for measuring spermidine synthase activity.

Novel chemical agents comprising an adenosine moiety or an adenosine analog moiety and an imaging moiety and methods of their use

The present invention is directed to novel chemical agents for compounds and their use for imaging myocardial perfusion. The invention also is directed to a kit for forming such novel agents. The chemical agents for the present invention comprising (a) an adenosine analog moiety or an adenosine moiety, and (b) an imaging moiety.