Cas no 152218-23-0 (Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI))

Adenosine, N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) is a chemically modified adenosine derivative featuring a cyclic phosphorothioate backbone and butanoyl esterification at the 2'-position. This structural modification enhances its stability against enzymatic degradation, making it suitable for applications requiring prolonged biological activity. The phosphorothioate linkage improves resistance to hydrolysis, while the butanoyl group may influence lipophilicity and membrane permeability. Such derivatives are often explored for their potential in nucleotide-based therapeutics, including prodrug strategies or targeted delivery systems. The compound's unique structure offers opportunities for research in signal transduction modulation and drug development, particularly where controlled release or enhanced bioavailability is desired.
Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) structure
152218-23-0 structure
Product Name:Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI)
CAS No:152218-23-0
MF:C14H17N5NaO6PS
MW:437.343212842941
CID:99317
PubChem ID:44755105
Update Time:2025-05-20

Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) Chemical and Physical Properties

Names and Identifiers

    • Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI)
    • 2'- O- MONOBUTYRYLADENOSINE- 3', 5'- CYCLIC MONOPHOSPHOROTHIOATE, RP- ISOMER ( RP-2'-O-MB-CAMPS )
    • Rp-2′-O-Monobutyryladenosine 3′,5′-cyclic monophosphorothioate
    • [(4aR,6R,7R,7aR)-6-(6-aminopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate
    • Rp-2'-O-MB-cAMPS
    • RP-MB-CAMPS, NA
    • sodiumsalt(sp-mb-camps)
    • sodiumsalt(rp-mb-camps)
    • RP-2'-O-MB-CAMPS SODIUM SALT
    • SP-2'-O-MB-CAMPS SODIUM SALT
    • rp-2'-o-monobutyryladenosine 3',5'-cyclic monophosphorothioate
    • 2’-o-monobutyryladenosine-3’,5’-cyclicmonophosphorothioate,sp-isomer
    • Rp-2′-O-Monobutyryladenosine 3′,5′-cyclic monophosphorothioate >97% (HPLC), solid
    • 2'-O-MONOBUTYRYLADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, SP-ISOMER SODIUM SALT
    • 2'-O-MONOBUTYRYLADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT
    • 2/'-O-MONOBUTYRYLADENOSINE-3/',5/'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT
    • 2'-O-Monobutyryladenosine-3',5'-cyclic monophosphorothioate,rp-isomer sodium salt
    • sodium;[(4aR,6R,7R,7aR)-6-(6-aminopurin-9-yl)-2-oxido-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate
    • Adenosine 3?,5?-cyclic Monophosphorothioate, 2?-O-Monobutyryl-, Rp-Isomer, Sodium Salt
    • J-008903
    • 152218-23-0
    • Inchi: 1S/C14H18N5O6PS.Na/c1-2-3-8(20)24-11-10-7(4-22-26(21,27)25-10)23-14(11)19-6-18-9-12(15)16-5-17-13(9)19;/h5-7,10-11,14H,2-4H2,1H3,(H,21,27)(H2,15,16,17);/q;+1/p-1/t7-,10-,11-,14-,26?;/m1./s1
    • InChI Key: FZOXLIBSZNOQJC-LLBCGFEYSA-M
    • SMILES: S=P1([O-])OC[C@@H]2[C@H]([C@H]([C@H](N3C=NC4C(N)=NC=NC3=4)O2)OC(CCC)=O)O1.[Na+]

Computed Properties

  • Exact Mass: 437.05300
  • Monoisotopic Mass: 437.05348573g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 11
  • Heavy Atom Count: 28
  • Rotatable Bond Count: 5
  • Complexity: 637
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 179?2

Experimental Properties

  • PSA: 188.57000
  • LogP: 2.32000

Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) Security Information

Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHENG KE LU SI SHENG WU JI SHU
sc-391041-5 μmol
Adenosine 3′,5′-cyclic Monophosphorothioate, 2′-O-Monobutyryl-, Rp-Isomer, Sodium Salt,
152218-23-0
5 μmol
¥4889.00 2023-09-05

Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) Related Literature

Additional information on Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI)

Recent Advances in the Study of Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) and Its Implications in Chemical Biology and Medicine

The compound Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI), with the CAS number 152218-23-0, has recently garnered significant attention in the field of chemical biology and medicinal chemistry. This molecule, a modified adenosine derivative, exhibits unique properties that make it a promising candidate for therapeutic applications, particularly in the modulation of adenosine receptor signaling pathways. Recent studies have focused on its synthesis, structural characterization, and biological activity, shedding light on its potential as a novel pharmacological agent.

The synthesis of this compound involves a series of sophisticated chemical modifications to the adenosine backbone, including the introduction of a butanoyl group at the N(6) position and a cyclic phosphorothioate moiety at the 3',5' positions. These modifications enhance the molecule's stability and bioavailability, addressing some of the limitations associated with natural adenosine derivatives. Researchers have employed advanced techniques such as NMR spectroscopy and mass spectrometry to confirm the structure and purity of the compound, ensuring its suitability for further biological evaluation.

In vitro and in vivo studies have demonstrated that Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) exhibits potent agonist activity at specific adenosine receptor subtypes, particularly the A1 and A2A receptors. This activity has been linked to its ability to modulate intracellular cAMP levels, leading to downstream effects on cell proliferation, inflammation, and apoptosis. Notably, the compound has shown promise in preclinical models of inflammatory diseases and neurodegenerative disorders, where adenosine receptor modulation plays a critical role in disease progression.

One of the most significant findings from recent research is the compound's improved metabolic stability compared to unmodified adenosine analogs. The phosphorothioate linkage and butanoyl group confer resistance to enzymatic degradation, prolonging its half-life in biological systems. This property is particularly advantageous for therapeutic applications, as it reduces the frequency of dosing and enhances the compound's efficacy. Additionally, the molecule's ability to cross the blood-brain barrier has sparked interest in its potential for treating central nervous system disorders.

Despite these promising results, challenges remain in the development of Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) as a therapeutic agent. Issues such as off-target effects, dose-dependent toxicity, and formulation optimization need to be addressed in future studies. Researchers are currently exploring structure-activity relationships (SAR) to design derivatives with improved selectivity and reduced side effects. Collaborative efforts between chemists, biologists, and pharmacologists are essential to advance this compound through the drug development pipeline.

In conclusion, the recent advancements in the study of Adenosine,N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphorothioate) 2'-butanoate (9CI) highlight its potential as a versatile tool in chemical biology and a promising candidate for therapeutic development. Its unique structural features and biological activities make it a valuable addition to the arsenal of adenosine receptor modulators. Continued research in this area is expected to yield further insights into its mechanisms of action and therapeutic applications, paving the way for its translation into clinical settings.

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