362-75-4

Usage

Uses

Used in Organic Chemical Synthesis:
2',3'-O-Isopropylideneadenosine is used as an intermediate in the synthesis of various organic compounds, particularly those related to nucleosides and nucleotides. Its stability and unique structure make it a valuable building block for the development of new molecules with potential applications in pharmaceuticals, diagnostics, and other areas of biotechnology.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2',3'-O-Isopropylideneadenosine is used as a key intermediate for the synthesis of modified nucleosides with potential therapeutic applications. These modified nucleosides can be used as antiviral, anticancer, or anti-inflammatory agents, among others. The isopropylidine group in IsoA provides additional protection to the molecule, which can be beneficial in the development of more stable and effective drugs.
Used in Research and Development:
2',3'-O-Isopropylideneadenosine is also used in research and development for the study of nucleic acid chemistry and the development of new methodologies for nucleoside synthesis. Its crystalline nature and unique chemical properties make it an attractive candidate for exploring novel reactions and understanding the fundamental aspects of nucleoside chemistry.

Upstream product

• 67-64-1 acetone 
• 58-61-7 adenosine 
• 66728-92-5 2'-O,3'-O-isopropylidene-8-phenylthioadenosine 
• 19083-21-7 2',3'-O-isopropylidene-N₆,N₆'-dimethyladenosine 
• 109680-73-1 [(3aR,4R,6R,6aR)-2,2-Dimethyl-6-(6-pyrrolidin-1-yl-purin-9-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-methanol 
• 109680-74-2 9-(2,3-Ο-isopropylidene-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine 
• 109680-75-3 N-Ethyl-N-[9-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-acetamide 
• 103022-64-6 5'-acetyl-N⁶,N⁶-di-p-toluyl-2',3'-O-isopropylideneadenosine 
• 4566-77-2 ((3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 13089-45-7 8-bromo-2',3'-O-isopropylene adenosine 
• 74848-81-0 {(3aR,4R,6R,6aR)-6-[6-(Ethoxymethyl-amino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-methanol 
• 74-89-5 methylamine 
• 77-76-9 2,2-dimethoxy-propane 
• 40635-67-4 acetoxyisobutyryl bromide 

Downstream Products

• 80860-44-2 2-[[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl]-2,3-dihydro-1H-isoindol-1,3-dione 
• 51008-69-6 2',3'-O-isopropylidene-N⁶,N⁶,5'-O-tri-p-toluyladenosine 
• 93135-73-0 2',3'-O-isopropylidene-5'-O-p-toluyladenosine 
• 93135-72-9 N⁶,5'-O-di-p-toluyl-2',3'-O-isopropylideneadenosine 
• 93135-74-1 7,8-dihydro-N⁶,7-di-p-toluyl-2',3'-O-isopropylidene-8,5'-O-cycloadenosine 
• 119244-39-2 9-[(3aR,4R,6S,6aS)-6-(4-Methoxy-phenylsulfanylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ylamine 
• 93180-04-2 Phosphoric acid (3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester bis-(2-chloro-phenyl) ester 
• 112107-21-8 (9-{(3aR,4R,6R,6aR)-6-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-yl)-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine 
• 68074-34-0 O^5'-(4,4'-dimethoxy-trityl)-O^2'_,O3'-isopropylidene-adenosine 
• 74334-88-6 2',3'-O-Isopropylidene-5'-O-diphenylphosphinothioyladenosine 
• 83355-91-3 2',3'-O-isopropylidene-5'-O-(p,p'-dianisylphosphinyl)adenosine 
• 93135-67-2 2',3'-O-isopropylidene-N⁶,N⁶,5'-O-tris(p-cyanobenzoyl)adenosine 
• 93135-68-3 7,8-dihydro-2',3'-O-isopropylidene-N⁶,N⁶,7-tris(p-cyanobenzoyl)-8,5'-O-cycloadenosine 
• 103022-65-7 4-cyano-5-p-cyanobenzoylamino-1-(5-O-p-cyanobenzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole 

Relevant academic research and scientific papers

Copper-Catalyzed Intramolecular Alkoxylation of Purine Nucleosides: One-Step Synthesis of 5′-O,8-Cyclopurine Nucleosides

A novel copper-catalyzed intramolecular dehydrogenative alkoxylation of purine nucleosides has been developed successfully, providing the 5′-O,8-cyclopurine nucleosides in one-step with a yield up to 90%. The method, which utilized an inexpensive CuCl catalyst and a di-tert-butyl peroxide (DTBP) oxidant was suitable in a broad substrate scope and proceeded well even in gram scale.

Protein arginine allylation and subsequent fluorophore targeting

Protein allylation and fluorophore targeting: Arginine residues of the yeast nuclear ribonucleoprotein Npl3 were extensively modified by Hmt1-catalyzed allylation reaction with allyl-SAM as the allyl group donor. The allylated protein was further treated with tetrazole compounds under UV irradiation, leading to formation of protein-attached fluorescent products.

Synthesis and cytostatical evaluation of cytidine- and adenosine-5'-hexadecylphosphate and their phosphonate analogs

Four phospholipid conjugates containing the non-cytotoxic nucleosides cytidine and adenosine were prepared by condensation reactions, and their cytotoxic activity was tested in vitro against the human immortalized mammary epithelial cell H184 A1N4, the human mammary tumor cells MaTu and MCF7 and the B lymphoblast cell line Daudi. The synthesized compounds showed considerable activity towards H184 A1N4, MaTu and Daudi cells, but they were not effective against MCF7 cells. The phosphorus moiety - either monophosphate or monophosphonate - does not influence the effectiveness of the phospholipid derivatives in the case of the solid tumor cell lines and H184 A1N4. The leukemic Daudi cell line is strongly sensitive towards the different types of ester as well as to the type of the nucleoside component. Adenosine-5'-hexadecylphosphate proved to be the most potent compound among the substances prepared (IC50: 9.0 μmol).

5'2-(N -aminoacyl)-sulfonamido-5'2-deoxyadenosine: Attempts for a stable alternative for aminoacyl-sulfamoyl adenosines as aaRS inhibitors

Synthesis of aminoacyl-sulfamoyl adenosines (aaSAs) and their peptidyl conjugates as aminoacyl tRNA synthetase (aaRS) inhibitors remains problematic due to the low yield of the aminoacylation and the subsequent conjugation reaction causing concomitant formation of a cyclic adenosine derivative. In an effort to reduce this undesirable side reaction, we aimed to prepare the corresponding aminoacyl sulfonamide (aaSoA) analogues as more stable alternatives for aaSA derivatives. Deletion of the 5'2-oxygen in aaSA analogues should render the C-5'2 less electrophilic and therefore improve the stability of the aminoacyl sulfamate analogues. We therefore synthesized six sulfonamides and compared their activity against the respective aaSA analogues. However, except for the aspartyl derivative, the new compounds are not able to inhibit the corresponding aaRS. Possible reasons for this loss of activity are discussed by modeling and comparison of the newly synthesized aaSoA derivatives with their parent aaSA analogues.

Charge-Tagged DNA Radicals in the Gas Phase Characterized by UV/Vis Photodissociation Action Spectroscopy

Adenosine radicals tagged with a fixed-charge group were generated in the gas phase and structurally characterized by tandem mass spectrometry, deuterium labeling, and UV/Vis action spectroscopy. Experimental results in combination with Born–Oppenheimer molecular dynamics, ab initio, and excited-state calculations led to unambiguous assignment of adenosine radicals as N-7 hydrogen atom adducts. The charge-tagged radicals were found to be electronically equivalent to natural DNA nucleoside radicals.

Potential utility of adenosine 5′-ester prodrugs to enhance its plasma half-life: Synthesis and molecular docking studies

Adenosine, the adenine nucleoside, has demonstrated various pharmacological properties related to the treatment of relevant clinical diseases. With respect to this, one of the most fascinating biological activities of adenosine is its capacity for reversing hepatic fibrosis, which has been established in several in vitro and in vivo studies. Although adenosine seems to be a privileged compound, it lacks of metabolic stability to be considered as a drug candidate. For this reason, in this preliminary study, six prodrugs were developed in order to enhance the plasma half-life of adenosine, in which the esterification at 5′ position of adenosine was considered. According to previous works, the increase in steric hindrance at this position could develop unfavorable interactions inside adenosine deaminase (ADA) catalytic domain, which is reported as the main enzyme implicated in adenosine metabolism. Besides, molecular docking was employed to verify if the hindrance at carbinol group in the prodrugs is enough to diminish its oxidation and also to predict if compounds would be metabolized by a promiscuous esterase. Finally, the in vitro assays corroborated the theoretical findings and also indicated that the compounds are less metabolized than adenosine by ADA; in the case of compounds containing proline and thioproline progroups (4d and 4e, respectively), the reduction was more than three-fold of decrease.

Design, Synthesis, and Characterization of Sulfamide and Sulfamate Nucleotidomimetic Inhibitors of hHint1

Hint1 has recently emerged to be an important target of interest due to its involvement in the regulation of a broad range of CNS functions including opioid signaling, tolerance, neuropathic pain, and nicotine dependence. A series of inhibitors were rationally designed, synthesized, and tested for their inhibitory activity against hHint1 using isothermal titration calorimetry (ITC). The studies resulted in the development of the first small-molecule inhibitors of hHint1 with submicromolar binding affinities. A combination of thermodynamic and high-resolution X-ray crystallographic studies provides an insight into the biomolecular recognition of ligands by hHint1. These novel inhibitors have potential utility as molecular probes to better understand the role and function of hHint1 in the CNS.

Chemical Proteomics Approach for Profiling the NAD Interactome

Nicotinamide adenine dinucleotide (NAD+) is a multifunctional molecule. Beyond redox metabolism, NAD+ has an equally important function as a substrate for post-translational modification enzymes, the largest family being the poly-ADP-ribose polymerases (PARPs, 17 family members in humans). The recent surprising discoveries of noncanonical NAD (NAD+/NADH)-binding proteins suggests that the NAD interactome is likely larger than previously thought; yet, broadly useful chemical tools for profiling and discovering NAD-binding proteins do not exist. Here, we describe the design, synthesis, and validation of clickable, photoaffinity labeling (PAL) probes, 2- and 6-ad-BAD, for interrogating the NAD interactome. We found that 2-ad-BAD efficiently labels PARPs in a UV-dependent manner. Chemical proteomics experiments with 2- and 6-ad-BAD identified known and unknown NAD+/NADH-binding proteins. Together, our study shows the utility of 2- and 6-ad-BAD as clickable PAL NAD probes.

NOVEL HISTONE METHYLTRANSFERASE INHIBITORS

The present invention relates to novel compounds of formula (I) as defined herein. The compounds are inhibitors of histone methyltransferases of the seven-beta-strand family, in particular of KMT9.

Tightly linked morpholino-nucleoside chimeras: new, compact cationic oligonucleotide analogues

The polyanionic phosphodiester backbone of nucleic acids contributes to high nuclease sensitivity and low cellular uptake and is therefore a major obstacle to the biological application of native oligonucleotides. Backbone modifications, particularly charge alterations is a proven strategy to provide artificial oligonucleotides with improved properties. Here, we describe the synthesis of a new type of oligonucleotide analogues consisting of a morpholino and a ribo- or deoxyribonucleoside in which the 5′-amino group of the nucleoside unit provides the nitrogen of the morpholine ring. The synthetic protocol is compatible with trityl and dimethoxytrityl protecting groups and azido functionality, and was extended to the synthesis of higher oligomers. The chimeras are positively charged in aqueous medium, due to theN-alkylated tertiary amine structure of the morpholino unit.