31281-86-4Relevant academic research and scientific papers
Synthesis and adenosine receptor affinity and potency of 8-alkynyl derivatives of adenosine
Lambertucci,Costanzi,Vittori,Volpini,Cristalli
, p. 1153 - 1157 (2001)
Adenosine derivatives bearing different (ar)alkynyl chains at the 8-position were synthesized and tested at human adenosine receptors. Binding studies showed that all compounds possess affinity for the A3 subtype in the high nM range. Moreover, guanosine 5′-O-(3-[35S]thio)triphosphate binding assay indicated that the 8-alkynyl adenosines behaved as antagonists of NECA at A3 receptors.
Selective C8-Metalation of Purine Nucleosides via Oxidative Addition
Kampert, Florian,Brackemeyer, Dirk,Tan, Tristan Tsai Yuan,Ekkehardt Hahn
, p. 4181 - 4185 (2018/11/23)
8-Bromo-2′-deoxy-3′,5′-di-O-acetylguanosine (1), 8-bromo-2′,3′,5′-tri-O-acetylguanosine (2), 8-bromo-2′-deoxy-3′,5′-di-O-acetyladenosine (3), and 8-bromo-2′,3′,5′-tri-O-acetyladenosine (4) react with [Pd(PPh3)4] via a C8-Br oxidative addition to give the C8-palladated azolato complexes [5]-[8] featuring an unprotonated N7 ring nitrogen atom. The complexes feature diastereotopic trans-disposed triphenylphosphine ligands, which allowed the determination of 2JPP for complexes of the type trans-[PdL2(PPh3)2] (2JPP = 442 Hz for [7]). In addition, two complex molecules of [7] form a trans-Watson-Crick/Hoogsteen AA base pair in the solid state. N7-protonation of the guanosine-derived complexes [5] and [6] with HBF4·Et2O and of adenosine-derived complexes [7] and [8] using lutidinium triflate yields complexes [9]BF4 and [10]BF4 and complexes [11]OTf and [12]OTf bearing protic NH,NR-NHC ligands derived from guanosine and adenosine, respectively.
Identification of 8-aminoadenosine derivatives as a new class of human concentrative nucleoside transporter 2 inhibitors
Tatani, Kazuya,Hiratochi, Masahiro,Nonaka, Yoshinori,Isaji, Masayuki,Shuto, Satoshi
supporting information, p. 244 - 248 (2015/03/30)
Purine-rich foods have long been suspected as a major cause of hyperuricemia. We hypothesized that inhibition of human concentrative nucleoside transporter 2 (hCNT2) would suppress increases in serum urate levels derived from dietary purines. To test this hypothesis, the development of potent hCNT2 inhibitors was required. By modifying adenosine, an hCNT2 substrate, we successfully identified 8-aminoadenosine derivatives as a new class of hCNT2 inhibitors. Compound 12 moderately inhibited hCNT2 (IC50 = 52 ± 3.8 μM), and subsequent structure-activity relationship studies led to the discovery of compound 48 (IC50 = 0.64 ± 0.19 μM). Here we describe significant findings about structural requirements of 8-aminoadenosine derivatives for exhibiting potent hCNT2 inhibitory activity.
Diadenosine antibacterial compounds
-
Page/Page column 12, (2012/07/14)
The present invention relates to compounds of formula (I): wherein R1, R2, R3, R4, X1, X2, X3 and Z are as defined in claim 1.The compounds are useful in the prevention and/or treatment of bacterial infections.
NOVEL ANTIBACTERIAL COMPOUNDS
-
Page/Page column 17, (2012/07/14)
The present invention relates to compounds of formula (I): wherein Rj, R2, R3, R4, Xi, X2, X3 and Z are as defined in claim 1. The compounds are useful in the prevention and/or treatment of bacterial infections.
PURINE NUCLEOTIDE DERIVATIVES
-
Page/Page column 21; 42, (2010/02/15)
This invention provides novel 8-carbyl substituted cAMPS and a novel procedures for the preparation of 8-Br-cAMP, a key starting material.
Cytostatic 6-arylpurine nucleosides V.+ synthesis of 8-substituted 6-phenylpurine ribonucleosides
Hocek, Michal,Hockova, Dana,Stambasky, Jan
, p. 837 - 848 (2007/10/03)
Regioselective Suzuki-Miyaura reaction of 8-bromo-6-iodo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine with phenylboronic acid gave 8-bromo-6-phenylpurine derivative that was used for cross-coupling reactions (with PhB(OH)2, Me3Al, Et3Al, BnZnCl) or nucleophilic substitutions (with NaOH, NaOMe, NH3, NHMe2 or thiourea). A series of 8-X-substituted 6-phenyl-9-(β-D-ribofuranosyl)purines (X = Ph, Me, Et, Bn, OH, OMe, NH2, NMe2, SH) was prepared in this way directly or after deprotection. None of the title nucleosides exhibited any considerable cytostatic activity.
DISTINCT SOLVENT-DEPENDENCE IN THE PHOTOREACTIONS OF PURINE NUCLEOSIDES WITH PYRIMIDOPTERIDINETETRONE N-OXIDE: POSSIBLE GENERATION OF HYDROXYL RADICAL FROM THE EXCITED N-OXIDE IN ALCOHOLS
Maki, Yoshifumi,Makino, Toru,Hirota, Kosaku,Sako, Magoichi
, p. 325 - 337 (2007/10/02)
Photoreaction of 2',3',5'-tri-O-acetyladenosine (5) with pyrimidopteridinetetrone N-oxide (1) in acetonitrile gave N6-cyanomethyl-2',3',5'-tri-O-acetyladenosine (6) as a major detectable product via coupling of adenosyl radical with cyanomethyl radical generated by the mediation of 1.Under the analogous conditions, N2-benzoyl-2',3',5'-tri-O-acetylguanosine (8) underwent oxidative degradation of the guanine skeleton by 1.In sharp contrast, photoreactions of 5 and 8 with 1 in tert-butanol resulted in the formation of the corresponding 8-hydroxypurine nucleosides (7) and (9), respectively.These facts and other observations suggest that 1 could generate hydroxyl radical upon irradiation in alcohols.
PERMANGANATE OXIDATION OF N6,N6,8-TRISUBSTITUTED-2',3',5'-TRI-O-ACETYLADENOSINES
Kato, Tetsuo,Ogawa, Shuichi,Ito, Isoo
, p. 3205 - 3208 (2007/10/02)
Oxidation of 2',3',5'-tri-O-acetyl derivatives of N6,N6-dialkyl-adenosines(3a-g) with KMnO4 in 50percent AcOH gave both the mono(5a-g) and didealkylderivati3es(6a-c) ; it was conclusiveoly proved that one and two methylene groups of the title nucleosides(3a-g) in the α position to the exocyclic nitrogen atom were simultaneously oxidized.
