- Supported Synthesis of Adenosine Nucleotides and Derivatives on a Benzene-Centered Tripodal Soluble Support
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The first soluble-phase synthesis of adenosine nucleotides including α,β and β,γ-methylene bisphosphonate analogues on a multi-pod support is reported. Anchoring of a 2’,3’-protected purine nucleoside to the tripodal support via the nucleobase was successfully achieved using a microwave assisted Cu(I)-catalyzed azide-alkyne cycloaddition. Then, phosphorylation was performed, followed by cleavage with aqueous ammonia to provide adenine derivatives, and finally deprotection. When using benzylamine instead of ammonia, a derivative with N6-benzylamine adenine as nucleobase was obtained. This methodology allows to access adenosine 5’-mono, di and triphosphates, as well as various analogues of pharmacological interest in modest to good yields.
- Appy, Lucie,Peyrottes, Suzanne,Roy, Béatrice
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- Expeditious synthesis and biological evaluation of new C-6 1,2,3-triazole adenosine derivatives A1 receptor antagonists or agonists
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The synthesis of new C-6 1,2,3-triazole adenosine derivatives via microwave assisted 1,3-dipolar cycloaddition as key step is described. The binding on membranes of cells that over express A1 adenosine receptors (A 1AR) was also evaluated. Among them, four compounds increased cAMP production, in a dose-dependent manner acting as antagonists of the A 1AR, while two compounds act as agonists.
- Mathew, Smitha C.,By, Youlet,Berthault, Aurelie,Virolleaud, Marie-Alice,Carrega, Louis,Chouraqui, Gaelle,Commeiras, Laurent,Condo, Jocelyne,Attolini, Mireille,Gaudel-Siri, Anouk,Ruf, Jean,Rodriguez, Jean,Parrain, Jean-Luc,Guieu, Regis
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experimental part
p. 3874 - 3881
(2010/09/17)
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- Convenient synthesis of 8-amino-2′-deoxyadenosine
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We studied the behaviour of 8-azido-2′-deoxyadenosine and 8-bromo-2′-deoxyadenosine in aqueous solutions of ammonia and primary and secondary amines. Unexpectedly, 8-Azido-2′-deoxyadenosine is converted to 8-amino-2′-deoxyadenosine in excellent yields. The use of this reaction for the preparation of 8-aminoadenine derivatives needed for the preparation of oligonucleotides carrying 8-aminoadenine is discussed.
- Frieden, Miriam,Avino, Anna,Eritja, Ramon
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p. 193 - 202
(2007/10/03)
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