Adenosine, 8-bromo-, cyclic 3',5'-(hydrogen phosphate)

Base Information

• Chemical Name: Adenosine, 8-bromo-, cyclic 3',5'-(hydrogen phosphate)
• CAS No.: 23583-48-4
• Molecular Formula: C10H11 Br N5 O6 P
• Molecular Weight: 408.105
• Hs Code.: 29349990
• NSC Number: 171719
• DSSTox Substance ID: DTXSID20860305
• Wikidata: Q27165627
• Mol file: 23583-48-4.mol

Synonyms:8 Br Cyclic AMP;8 Bromo cAMP;8 Bromo Cyclic Adenosine Monophosphate;8 Bromo Cyclic Adenosine Monophosphate, Monosodium Salt;8 Bromo Cyclic Adenosine Monophosphate, Sodium Salt;8 Bromo Cyclic AMP;8 Bromoadenosine 3',5' Cyclic Monophosphate;8-Br Cyclic AMP;8-Bromo Cyclic Adenosine Monophosphate;8-Bromo Cyclic Adenosine Monophosphate, Monosodium Salt;8-Bromo Cyclic Adenosine Monophosphate, Sodium Salt;8-Bromo Cyclic AMP;8-Bromo-cAMP;8-Bromoadenosine 3',5'-Cyclic Monophosphate;AMP, Br Cycl;Br Cycl AMP;Cyclic AMP, 8-Br;Cyclic AMP, 8-Bromo

Chemical Property of Adenosine, 8-bromo-, cyclic 3',5'-(hydrogen phosphate)

Chemical Property:

• Melting Point: 254 °C (dec.)(lit.)
• Boiling Point: 741.9 °C at 760 mmHg
• PKA: 0.95±0.60(Predicted)
• Flash Point: 402.5 °C
• PSA: 164.65000
• Density: 2.8 g/cm³
• LogP: 0.52630
• Storage Temp.: −20°C
• Sensitive.: Hygroscopic
• Solubility.: aqueous base: soluble
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 1
• Exact Mass: 406.96303
• Heavy Atom Count: 23
• Complexity: 532

Purity/Quality:

98%,99%, ^*data from raw suppliers

8-Br-cAMP ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C(C(C(O2)N3C4=NC=NC(=C4N=C3Br)N)O)OP(=O)(O1)O
• Uses: 8-Bromoadenosine 3′,5′-cyclic monophosphate has been used:to treat H295R cells as positive controls for CYP19 inductionas a membrane permeable cAMP analog to study its effect on short-circuit current (Isc)to investigate its potential as an inducer of differentiation in Wharton′s jelly-derived mesenchymal stem cells (WJ-MSCs)

Technology Process of Adenosine, 8-bromo-, cyclic 3',5'-(hydrogen phosphate)

There total 4 articles about Adenosine, 8-bromo-, cyclic 3',5'-(hydrogen phosphate) 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: 76.0%

cAMP (60-92-4) → Br-cAMP (23583-48-4)

Guidance literature:

With bromine; sodium acetate; In water; at 20 ℃; for 24h;

DOI:10.1039/b702403g

Reference yield:

({4-[(2S,4aR,6R,7R,7aS)-6-(6-Amino-8-bromo-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-yloxymethyl]-2-oxo-2H-chromen-7-yl}-carboxymethyl-amino)-acetic acid → 7-[bis(carboxymethyl)amino]-4-(hydroxymethyl)coumarin (876275-37-5) + Br-cAMP (23583-48-4)

Guidance literature:

With HEPES buffer; In water; acetonitrile; pH=7.2; Quantum yield; UV-irradiation;

DOI:10.1002/anie.200502411

Reference yield:

({4-[(2R,4aR,6R,7R,7aS)-6-(6-Amino-8-bromo-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-yloxymethyl]-2-oxo-2H-chromen-7-yl}-carboxymethyl-amino)-acetic acid → 7-[bis(carboxymethyl)amino]-4-(hydroxymethyl)coumarin (876275-37-5) + Br-cAMP (23583-48-4)

Guidance literature:

With HEPES buffer; In water; acetonitrile; pH=7.2; Quantum yield; UV-irradiation;

DOI:10.1002/anie.200502411

upstream raw materials:

cAMP

Downstream raw materials:

(4aR,6R,7R,7aS)-6-(6-Amino-8-cyclohexylsulfanyl-purin-9-yl)-2-oxo-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

(4aR,6R,7R,7aS)-6-[6-Amino-8-(4-methoxy-phenylsulfanyl)-purin-9-yl]-2-oxo-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

8-Benzylselenoadenosin-3',5'-phosphorsaeure

(4aR,6R,7R,7aS)-6-(6-Amino-8-o-tolylsulfanyl-purin-9-yl)-2-oxo-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Refernces

• 1、 Myasoedov et al.. "-". . . Retrieved 1979.
• 2、 Andrei, Mioara,Bjornstad, Vidar,Langli, Geir,Romming, Christian,Klaveness, Jo,Tasken, Kjetil,Undheim, Kjell. "Stereoselective preparation of (RP)-8-hetaryladenosine-3′, 5′-cyclic phosphorothioic acids". . p. 2070 - 2080. Retrieved 2008/03/12.
• 3、 -. "PURINE NUCLEOTIDE DERIVATIVES". Page/Page column 64. . Retrieved 2010/02/15.