362-75-4

Basic information

• Product Name: 2',3'-O-Isopropylideneadenosine
• Synonyms: 6-Amino-9-(2-O,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine;2',3'-O-Isopropylideneadenosine,98%;9-(2,3-O-Isopropylidene-beta-D-ribofuranosyl)adenin;2,3-Isopropylideneadeosine;2',3'-O-(1-Methylethylidene)adenosine;NSC 29413;2',3'-Di-O-isopropylidene adenosine;ISOPROPYLIDENE ADENOSINE
• CAS NO: 362-75-4
• Molecular Formula: C₁₃H₁₇N₅O₄
• Molecular Weight: 307.31
• EINECS: 206-650-3
• Product Categories: API intermediates;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides;Nucleosides;Oligonucleotide Synthesis;Specialty Synthesis
• Mol File: 362-75-4.mol
• Article Data: 91

Chemical Properties

• Melting Point: 221-222 °C(lit.)
• Boiling Point: 447.81°C (rough estimate)
• Flash Point: 298.8 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.2370 (rough estimate)
• Refractive Index: -105 ° (C=1, Dioxane)
• Storage Temp.: Store at RT.
• Solubility: Dioxane (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.14±0.10(Predicted)
• BRN: 43435
• CAS DataBase Reference: 2',3'-O-Isopropylideneadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-O-Isopropylideneadenosine(362-75-4)
• EPA Substance Registry System: 2',3'-O-Isopropylideneadenosine(362-75-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 362-75-4(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

Uses

2',3'-O-Isopropylideneadenosine is used as an organic chemical synthesis intermediate.

Upstream product

• 67-64-1 acetone 
• 58-61-7 adenosine 
• 74-89-5 methylamine 
• 39947-05-2 ((3aR,4R,6R,6aR)-6-(6-benzamido-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 
• 4744-10-9 dimethoxypropane 
• 77-76-9 2,2-dimethoxy-propane 
• 104-15-4 toluene-4-sulfonic acid 
• 149-73-5 trimethyl orthoformate 
• 15888-38-7 5'-acetyl-2',3'-isopropylideneadenosine 
• 13089-45-7 8-bromo-2',3'-O-isopropylene adenosine 
• 122-51-0 orthoformic acid triethyl ester 
• 109680-71-9 ((3aR,4R,6R,6aR)-6-(6-(diethylamino)-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 350498-62-3 5'-(anthraquinon-2-ylmethoxycarbonyl)-2',3'-O-isopropylideneadenosine 
• 350498-61-2 5'-(anthraquinon-2-ylmethoxycarbonyl)adenosine 

Downstream Products

• 10343-04-1 O^2',O^3'-isopropylidene-[5']adenylic acid dibenzyl ester 
• 29706-75-0 2',3'-O-isopropylidene-⁶N-dimethylaminomethylene adenosine 
• 61-19-8 5'-adenosine monophosphate 
• 58-61-7 adenosine 
• 15888-38-7 5'-acetyl-2',3'-isopropylideneadenosine 
• 439097-83-3 6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 
• 2140-11-6 2',3'-O-isopropylidene inosine 
• 862490-61-7 [[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-(2-nitro-benzenesulfonyl)-amino]-acetic acid ethyl ester 
• 34245-48-2 5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine 
• 78111-39-4 5'-diphenylphosphate-5'-deoxy-2',3'-isopropylidene adenosine 
• 104264-32-6 O^5'-(N-benzyloxycarbonyl-L-phenylalanyl)-O^2'_,O3'-isopropyliden-adenosine 
• 73-24-5 7H-purin-6-ylamine 
• 84365-04-8 5'-acetylthio-5'-deoxy-2',3'-O-isopropylidene adenosine 
• 93135-70-7 2',3'-O-(1-methylethylidene)-adenosyl 5'-benzoate 

Relevant articles and documents

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.

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).

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.

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.

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.

A pan-inhibitor for protein arginine methyltransferase family enzymes

Protein arginine methyltransferases (PRMTs) play important roles in transcription, splicing, DNA damage repair, RNA biology, and cellular metabolism. Thus, PRMTs have been attractive targets for various diseases. In this study, we reported the design and synthesis of a potent pan-inhibitor for PRMTs that tethers a thioadenosine and various substituted guanidino groups through a propyl linker. Compound II757 exhibits a half-maximal inhibition concentration (IC50 ) value of 5 to 555 nM for eight tested PRMTs, with the highest inhibition for PRMT4 (IC50 = 5 nM). The kinetic study demonstrated that II757 competitively binds at the SAM binding site of PRMT1. Notably, II757 is selective for PRMTs over a panel of other methyltransferases, which can serve as a general probe for PRMTs and a lead for further optimization to increase the selectivity for individual PRMT.