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1,3-Dideazaadenosine is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 20649-47-2 Structure
  • Basic information

    1. Product Name: 1,3-Dideazaadenosine
    2. Synonyms: 1,3-Dideazaadenosine
    3. CAS NO:20649-47-2
    4. Molecular Formula: C12H15N3O4
    5. Molecular Weight: 265.2652
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 20649-47-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 635°Cat760mmHg
    3. Flash Point: 337.9°C
    4. Appearance: /
    5. Density: 1.75g/cm3
    6. Vapor Pressure: 5.35E-17mmHg at 25°C
    7. Refractive Index: 1.775
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 1,3-Dideazaadenosine(CAS DataBase Reference)
    11. NIST Chemistry Reference: 1,3-Dideazaadenosine(20649-47-2)
    12. EPA Substance Registry System: 1,3-Dideazaadenosine(20649-47-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 20649-47-2(Hazardous Substances Data)

20649-47-2 Usage

Chemical structure

1,3-Dideazaadenosine is structurally similar to adenosine, but with the removal of a nitrogen atom at the 3 position.

Inhibition

It is a potent inhibitor of the enzyme adenosine deaminase.

Role in metabolism

Adenosine deaminase plays a role in the regulation of purine metabolism.

Therapeutic applications

1,3-Dideazaadenosine has potential therapeutic applications in the treatment of a range of diseases, including cancer, autoimmune disorders, and inflammatory conditions.

Antiviral properties

It has been studied for its antiviral properties.

Immune response modulation

1,3-Dideazaadenosine has the ability to modulate immune responses.

Pharmaceutical development

Due to its unique chemical structure and biological activities, it is of interest in the development of novel pharmaceutical agents.

Check Digit Verification of cas no

The CAS Registry Mumber 20649-47-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,6,4 and 9 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 20649-47:
(7*2)+(6*0)+(5*6)+(4*4)+(3*9)+(2*4)+(1*7)=102
102 % 10 = 2
So 20649-47-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H15N3O4/c13-6-2-1-3-7-9(6)14-5-15(7)12-11(18)10(17)8(4-16)19-12/h1-3,5,8,10-12,16-18H,4,13H2/t8-,10-,11-,12-/m1/s1

20649-47-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-Dideazaadenosine

1.2 Other means of identification

Product number -
Other names 9-(1'-β-D-ribofuranosyl)-1,3-dideazaadenine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:20649-47-2 SDS

20649-47-2Downstream Products

20649-47-2Relevant articles and documents

Synthesis and antimicrobial activity of some novel nucleoside analogues of adenosine and 1,3-dideazaadenosine

Srivastava, Richa,Bhargava, Anudita,Singh, Ramendra K.

, p. 6239 - 6244 (2007)

A number of nucleoside analogues have been synthesized and evaluated for their antibacterial and antifungal activities against Staphylococcus aureus, Group D Streptococcus, Pseudomonas aeruginosa, Proteus spp., Salmonella spp., Aspergillus fumigatus, Penicillium marneffei, Candida albicans, Cryptococcus neoformans, and Mucor spp. The compounds 1, 4, and 6 emerged as potent antibacterial agents with MIC values of 0.75, 0.38, and 0.19 μM, respectively, against group D Streptococcus. Further, the results suggest that the molecules 4, 6, and 7 would be potent antifungal agents as they show substantial degree of inhibition toward the growth of pathogenic fungi with MICs of 0.75, 0.38, and 0.38 μM, respectively.

The nucleoside transport proteins, NupC and NupG, from Escherichia coli: Specific structural motifs necessary for the binding of ligands

Patching, Simon G.,Baldwin, Stephen A.,Baldwin, Alexander D.,Young, James D.,Gallagher, Maurice P.,Henderson, Peter J. F.,Herbert, Richard B.

, p. 462 - 470 (2007/10/03)

A series of 46 natural nucleosides and analogues (mainly adenosine-based) were tested as inhibitors of [U-14C]uridine uptake by the concentrative, H+-linked nucleoside transport proteins NupC and NupG from Escherichia coli. The two evolutionarily unrelated transporters showed similar but distinct patterns of inhibition, revealing differing selectivities for the different nucleosides and their analogues. Binding of nucleosides to NupG required the presence of hydroxyl groups at each of the C-3′ and C-5′ positions of ribose, while binding to NupC required only the C-3′ hydroxyl substituent. The greater importance of the ribose moiety for binding to NupG is consistent with the evolutionary relationship between this protein and the oligosaccharide: H+ symporter (OHS) subfamily of the major facilitator superfamily (MFS) of transporters. For both proteins the natural α-configuration at C-3′ and the natural β-configuration at C-1′ was mandatory for ligand binding. N-7 in the imidazole ring of adenosine and the amino group at C-6 were found not to be important for binding and both transporters showed flexibility for substitution at C-6/N6; one or both of N-l and N-3 were important for adenosine analogue binding to NupC but significantly less so for binding to NupG. From the different effects of 8-bromoadenosine on the two transporters it appears that adenosine selectively binds to NupC in an anti- rather than a syn-conformation, whereas NupG is less prescriptive. The pattern of inhibition of NupC by differing nucleoside analogues confirmed the functional relationship of the bacterial transporter to members of the human concentrative nucleoside transporter (CNT) family and reaffirmed the use of the bacterial protein as an experimental model for these physiologically and clinically important mammalian proteins. The specificity data for NupG have been used to develop a homology model of the protein's binding site, based on the X-ray crystallographic structure of the disaccharide transporter LacY from E. coli. We have also developed an efficient general protocol for the synthesis of adenosine and three of its analogues, which is illustrated by the synthesis of [1′-13C]adenosine.

Synthesis and antiviral properties of arabino and ribonucleosides of 1,3-dideazaadenine, 4-nitro-1,3-dideazapurine and diketopiperazine

Sinha, Sarika,Srivastava, Richa,De Clercq, Erik,Singh, Ramendra K.

, p. 1815 - 1824 (2007/10/03)

Different arabinosides and ribosides, viz. Ara-DDA or 9(1-β-D- arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-β-D- arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or 1(1-β-D- arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-β-D-

An improved procedure for the synthesis of 1,3-dideazaadenosine

Devlin,Jebaratnam

, p. 711 - 718 (2007/10/02)

The preparation of the titled compound has been conveniently achieved in five steps, and in 43% overall yield. The large scale monoreduction of 2,6-dinitroaniline, and the stannic chloride catalyzed glycosylation of 4 to obtain 6 as the only product (86%) are two important reactions in this five step synthesis.

Derivatives of 1-β-D-ribofuranosylbenzimidazole 3',5'-phosphate that mimic the actions of adenosine 3',5'-phosphate (cAMP) and guanosine 3',5'-phosphate (cGMP)

Genieser, Hans-Gottfried,Winkler, Elisabeth,Butt, Elke,Zorn, Michaela,Schulz, Susanne,et al.

, p. 217 - 236 (2007/10/02)

A series of new analogues of 1-β-D-ribofuranosylbenzimidazole 3',5'-phosphate (cBIMP) has been designed according to the properties predicted by the MNDO method, and synthesised from substituted benzimidazoles.Dipole vectors and HOMO and LUMO energies for each benzimidazole base were calculated by MNDO method and the lipophilicities of the cBIMP derivatives were determined.In general, the cBIMP derivatives activate cAMP-dependent protein kinases I and II and preferentially bind to site B, especially for the type II kinase, with 2-trifluoromethyl-cBIMP and 5,6-difluoro-cBIMP exhibiting the highest site selectivity.Each cBIMP derivative can stimulate cGMP-stimulated cyclic phosphodiesterase (cGS-PDE), with 5,6-dimethyl-cBIMP being as potent as cGMP, and also inhibit cGMP-inhibited phosphodiesterase (cGI-PDE).Only the 2-trifluoromethyl-cBIMP and the Rp-phosphorothioates (cBIMPS) (equatorial P=S) were resistant to hydrolysis by cPDE.The Sp-phosphorothioates were hydrolysed slowly, if at all.In addition to exhibiting a high lipophilicity, the most active compounds for the induction of apoptosis and inhibition of proliferation were also resistant to cPDE (Sp-5,6-dichloro-cBIMPS) and/or were potent activators of cAMP-dependent protein kinase (5,6-dichloro-cBIMP).

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