Actosin

Base Information

• Chemical Name: Actosin
• CAS No.: 362-74-3
• Molecular Formula: C18H24N5O8P
• Molecular Weight: 469.391
• European Community (EC) Number: 206-649-8
• NSC Number: 143108
• DSSTox Substance ID: DTXSID40859352
• Wikipedia: Bucladesine
• Wikidata: Q27163331
• ChEMBL ID: CHEMBL1371908
• Mol file: 362-74-3.mol

Synonyms:Actosin;C18H24N5O8P.xNa;362-74-3;C18-H24-N5-O8-P.x-Na;C18H24N5O8P;C18-H24-N5-O8-P;NCGC00021144-02;N6,5'-phosphate;N6,5'-monophosphate;N6,5'-cyclic AMP;N6,5'-monophosphoric acid;N6,5'-cyclic monophosphate;N6,5'-(hydrogen phosphate);SCHEMBL163105;3',5'-Dibutyryl cyclic AMP;Dibutyryl cyclic 3',5'-AMP;N6,5'-adenosine monophosphate;CHEMBL1371908;CHEBI:91494;N6,5'-AMP;DTXSID40859352;BCP10476;N-(9-beta-D-ribofuranosyl-9H-purin-6-yl)butyramide cyclic 3',5'-(hydrogen phosphate) 2'-butyrate;NSC143108;N6,5'-cyclic adenosine monophosphate;AKOS015896463;NCGC00021144-03;NCGC00094988-01;NCGC00094988-02;NCI60_000948;FT-0629734;FT-0654177;Dibutyryl 3',5'-cyclic adenosine monophosphate;BRD-A04706586-236-01-7;Q27163331;Butyramide, 2'-butyrate cyclic 3',5'-(hydrogen phosphate);Butyramide, cyclic 3',5'-(hydrogen phosphate) 2'-butyrate;Bucladesine;3',5'-Cyclic AMP dibutyrate;Cyclic AMP dibutyrate;Dibutyryl 3',5'-Cyclic AMP;6-(6-Butanamido-9H-purin-9-yl)-2-hydroxy-2-oxotetrahydro-2H,4H-2lambda~5~-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl butanoate;butanoic acid [2-hydroxy-2-oxo-6-[6-(1-oxobutylamino)-9-purinyl]-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphorin-7-yl] ester

Chemical Property of Actosin

Chemical Property:

• Melting Point: 203 - 205 °C
• Refractive Index: 1.717
• PKA: 0.82±0.60(Predicted)
• PSA: 173.80000
• Density: 1.72 g/cm³
• LogP: 1.76300
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO; Methano
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 469.13624974
• Heavy Atom Count: 32
• Complexity: 759

Purity/Quality:

99% ^*data from raw suppliers

ButyryladenosineCyclophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)NC1=C2C(=NC=N1)N(C=N2)C3C(C4C(O3)COP(=O)(O4)O)OC(=O)CCC
• Description: Bucladesine is a cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed)
• Uses: Bucladesine is a cell permeable cAMP analog. The compound is used in a wide variety of research applications because it mimics cAMP and can induce normal physiological responses when added to cells in experimental conditions. cAMP is only able to elicit minimal responses in these situations. The neurite outgrowth instigated by bucladesine in cell cultures has been shown to be enhanced by nardosinone.

Technology Process of Actosin

There total 2 articles about Actosin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.09%

butanoic acid anhydride (106-31-0) + cAMP (60-92-4) → dibutyryl cyclic AMP (362-74-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80 ℃; for 7h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield:

→ dibutyryl cyclic AMP (362-74-3)

Guidance literature:

/BRN= 52645/,(CH3CH2CH2CO)2 O (Pyridin,(C2H5)3N, H2O, NaOH);

upstream raw materials:

butanoic acid anhydride

cAMP

Refernces