Structure–activity relationships of adenosines with heterocyclic N6-substituents

Syntheses of crystal structures andin vitrocytotoxic activities of new copper(II) complexes of pyridine-2,6-dicarboxylate

“…In biological systems, copper exists as a variety of complexes as coordinated forms of copper are more stable than the corresponding ionic species [8]. Several families of copper complexes comprising different ligands demonstrated notable anticancer activity [9][10][11][12][13][14][15]. Our choice of imidazole and pyridine derivatives is based on differences in their DNA binding ability.…”

Bicyclic β-amino acids

“…136d Boc-protected amino acid 267a was used in the synthesis of A 1 adenosine receptor ligands. 147 It was shown that derivative 327 is a reasonably potent A 1 agonist (IC 50 = 35 nM), while substitution on the bridging nitrogen with some alkoxycarbonyl moieties (e. g. Boc) further increased potency and selectivity of the compounds. Boc derivative of 267b was used in the synthesis of α7 nicotinic acetylcholine receptor agonists, some of which shown high potency and selectivity towards other related biological targets (e. g. 328, K i = 9 nM for α7 nAChR).…”

Synthesis and Biological Evaluation of Adenosines with Heterobicyclic and Polycyclic N6‐Substituents as Adenosine A1 Receptor Agonists

“…[12] Coupling of the groups, either using the respective anhydride (13,14) or succinimide (15)(16)(17), in the presence of sodium hydrogen carbonate in a mixture of N,N-dimethylformamide (DMF) and water resulted in monosubstitution of the more reactive secondary amine in moderate to good yields (34-73 %). With the 3-azabicyclo-[3.2.1]octane ring installed, deprotection of the Boc group was achieved using a saturated solution of hydrogen chloride gas in ethyl acetate.…”

“…[23] These structures possess properties that were expected to be beneficial for interaction with the N 6 -substituent binding pocket of A 1 R, such as relatively large cage size, high lipophilicity and conformational rigidity. [2,[10][11][12] [24,25] The synthesis of N 6 -tris-homocubanyladenosines 29 and 30, and N 6 -cubanyladenosine 31 was carried out from the hydrochloride salt of the respective amine and 6-chloropurine riboside under conditions identical to those previously described.…”

“…[12] The incorporation of selenium has been well noted as a common bioisosteric replacement for a related chalcogen. [12] The incorporation of selenium has been well noted as a common bioisosteric replacement for a related chalcogen.…”