78188-38-2

Usage

Uses

Used in Organic Synthesis:
N6-Benzyl-2’,3’-isopropylideneadenosine is used as a synthetic building block for the creation of various organic compounds. Its unique structure allows for the formation of new molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N6-Benzyl-2’,3’-isopropylideneadenosine is used as a key intermediate in the synthesis of adenosine receptor agonists and antagonists. These compounds have potential therapeutic applications in treating various conditions, such as asthma, chronic obstructive pulmonary disease (COPD), and cardiovascular disorders.
Used in Chemical Research:
N6-Benzyl-2’,3’-isopropylideneadenosine is also utilized in chemical research for studying the structure-activity relationships of adenosine derivatives. This helps in the development of more potent and selective adenosine receptor modulators with improved pharmacological properties.

InChI:InChI=1/C20H23N5O4/c1-20(2)28-15-13(9-26)27-19(16(15)29-20)25-11-24-14-17(22-10-23-18(14)25)21-8-12-6-4-3-5-7-12/h3-7,10-11,13,15-16,19,26H,8-9H2,1-2H3,(H,21,22,23)/t13-,15-,16-,19-/m1/s1

Upstream product

• 2004-06-0 6-Chloropurine riboside 
• 100-46-9 benzylamine 
• 39824-26-5 6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine 
• 4294-16-0 N₆-Benzyladenosine 
• 77-76-9 2,2-dimethoxy-propane 
• 109680-72-0 N⁶,N⁶-dibenzyl-2',3'-O-isopropylideneadenosine 

Downstream Products

• 1052239-48-1 N₆-benzyl-2',3'-O-isopropylidene-5'-O-(sulfamoyl)adenosine 
• 111109-99-0 (S)-2-amino-4-((((2S,3S,4R,5S)-5-(6-(benzylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid 
• 1338596-00-1 N^δ-[5'-(N⁶-benzyladenosyl)]-N^δ-(2-iodoethyl)-(S)-2,5-diaminopentanoic acid hydrochloride 
• 1338596-06-7 C₄₁H₆₁N₇O₁₀ 
• 1338596-03-4 C₂₂H₂₈N₆O₄ 
• 1010855-46-5 C₂₀H₂₄N₆O₃ 

Relevant academic research and scientific papers

DERIVATIVES OF GLYCERO-MANNO-HEPTOSE ADP FOR USE IN MODULATING IMMUNE RESPONSE

The disclosure provides compounds, compositions and methods related to activating alpha-kinase 1 (ALPK1) for modulating an immune response and treating or preventing cancer, infection, inflammation and related diseases and disorders as well as potentiating an immune response to a target antigen. The disclosure also provides heterocyclic compounds of formula (I) as agonists of alpha protein kinase 1 (ALPK1) and their use in activating ALPK1, modulating an immune response and treating diseases such as cancer, wherein A1, A2, L1, L2, L3, Z1, Z2, W1, W2, R1, R2, R3, R4, R5, R6 and R7 are as defined herein.

NUCLEOSIDE AND NUCLEOTIDE ANALOGUES AS CD73 INHIBITORS AND THERAPEUTIC USES THEREOF

Nucleoside and nucleotide compounds and analogues, and pharmaceutically acceptable compositions thereof, as inhibitors of CD73 for the treatment of diseases or disorders associated with CD73 activities, especially cancers, and methods of preparing these compounds are disclosed.

SAH derived potent and selective EZH2 inhibitors

A series of novel enhancer of zeste homolog 2 (EZH2) inhibitors was designed based on the chemical structure of the histone methyltransferase (HMT) inhibitor SAH (S-adenosyl-l-homocysteine). These nucleoside-based EZH2 inhibitors blocked the methylation of nucleosomes at H3K27 in biochemical assays employing both WT PRC2 complex as well as a Y641N mutant PRC2 complex. The most potent compound, 27, displayed IC50's against both complexes of 270 nM and 70 nM, respectively. To our knowledge, compound 27 is the most potent SAH-derived inhibitor of the EZH2 PRC2 complex yet identified. This compound also displayed improved potency, lipophilic efficiency (LipE), and selectivity profile against other lysine methyltransferases compared with SAH.

Inhibition of siderophore biosynthesis in Mycobacterium tuberculosis with nucleoside bisubstrate analogues: Structure-activity relationships of the nucleobase domain of 5′-O-[N-(salicyl)sulfamoyl]adenosine

5′-O-[N-(salicyl)sulfamoyl]adenosine (Sal-AMS) is a prototype for a new class of antitubercular agents that inhibit the aryl acid adenylating enzyme (AAAE) known as MbtA involved in biosynthesis of the mycobactins. Herein, we report the structure-based design, synthesis, biochemical, and biological evaluation of a comprehensive and systematic series of analogues, exploring the structure-activity relationship of the purine nucleobase domain of Sal-AMS. Significantly, 2-phenyl-Sal-AMS derivative 26 exhibited exceptionally potent antitubercular activity with an MIC99 under iron-deficient conditions of 0.049 μM while the N-6-cyclopropyl-Sal-AMS 16 led to improved potency and to a 64-enhancement in activity under iron-deficient conditions relative to iron-replete conditions, a phenotype concordant with the designed mechanism of action. The most potent MbtA inhibitors disclosed here display in vitro antitubercular activity superior to most current first line TB drugs, and these compounds are also expected to be useful against a wide range of pathogens that require aryl-capped siderphores for virulence.

Partial and full agonists of A1 adenosine receptors

Disclosed are novel compounds that are partial and full A1 adenosine receptor agonists, useful for treating various disease states, in particular tachycardia and atrial flutter, angina, myocardial infarction and hyperlipidemia.