5404-86-4Relevant articles and documents
Metal complexes of 6-pyrazolylpurine derivatives as models for metal-mediated base pairs
Sinha, Indranil,Hepp, Alexander,K?sters, Jutta,Müller, Jens
, p. 355 - 360 (2015)
6-(3,5-Dimethylpyrazol-1-yl)purine has recently been introduced as an artificial nucleobase for the specific recognition of canonical nucleobases via the formation of a metal-mediated base pair. We report here the synthesis and structural characterization by single crystal X-ray diffraction analysis of a series of metal complexes of the corresponding alkylated model nucleobases 9-methyl-6-(3,5-dimethylpyrazol-1-yl)purine 2 and 9-methyl-6-pyrazol-1-yl-purine 7. The sterically more demanding ligand 2 forms the Cu2 + complexes [Cu(2)(NO3)2] and [Cu(2)Cl2] with a 1:1 stoichiometry of ligand and metal ion. In contrast, ligand 7 forms complexes [Cu(7)2(NO3)](NO3) and [Ag(7)2](ClO4) with a 2:1 stoichiometry. The molecular structures of [Cu(2)(NO3)2] and [Cu(2)Cl2] confirm the previously suggested coordination pattern, i.e. Cu2 + is coordinated via the pyrazole nitrogen atom and the purine N7 position. The fact that different relative orientations of the two ligands in [Cu(7)2(NO3)](NO3) and [Ag(7)2](ClO4) are observed allows the prediction that the corresponding metal-mediated homo base pairs should be stable both in regular antiparallel-stranded and in the rare parallel-stranded double helices.
Design, Synthesis, and Anticancer Activity of Novel Fused Purine Analogues
Hassan,Sarg,Bayoumi,Kalaf
, p. 3458 - 3470 (2017/11/21)
6-Mercaptopurine has been utilized for the synthesis of various fused purine analogues through different chemical reactions to yield [1,4]thiazino[4,3,2-gh]purines 2, 3, 10a,b, 14, (8-oxo-[1,4]thiazino[4,3,2-gh]purin-7(8H)-ylidene) acetate 4, [1,4]thiazepino[4,3,2-gh]purine 6, thiazolo[3,4,5-gh]purine 7, imidazo[1,5,4-gh]purin-5-amine 8, 5-methylimidazo[1,5,4-gh]purine 9, [1,2,4]triazino[4,3-i]purines 16, 18, 21, [1,2,4]triazino[4,5,6-gh]purine 20, 5-methyl-2-(7H-purin-6-yl)-1H-pyrazol-3(2H)-one 22, [1,2,4]triazolo[4,3-i]purine 23, [1,2,5]triazepino[5,4,3-gh]purine 24, and ethyl 6-(2-(ethoxycarbonyl)hydrazinyl)-9H-purine-9-carboxylate 26. Seventeen of the newly synthesized compounds were selected by the NCI, Maryland, USA, and were tested for their anticancer activity in an initial single high dose in the full NCI 60 cell line panel among which [1,4]thiazino[4,3,2-gh]purine-7,8-dione 2, 7-benzyl-[1,4]thiazino[4,3,2-gh]purine 10b, and 3-(2,4-dimethoxyphenyl)-7H-[1,2,4]triazolo[4,3-i]purine 23 were found to possess very potent anticancer activity against most of the cancer cell lines.
Effect of the structure of adenosine mimic of bisubstrate-analog inhibitors on their activity towards basophilic protein kinases
Enkvist, Erki,Kriisa, Marie,Roben, Mart,Kadak, Grete,Raidaru, Gerda,Uri, Asko
scheme or table, p. 6098 - 6101 (2010/06/16)
Previously reported structural fragments that associate with the ATP-binding pocket of basophilic protein kinases were conjugated with d-arginine-containing peptides. Inhibitory potency of the resulting bisubstrate-analog inhibitors towards PKA and ROCK-II extended to subnanomolar range. The conjugates incorporating 2-pyrimidyl-5-amidothiophene fragment had the highest activity and at 100 nM concentration exhibited over 80% inhibition of most of the tested basophilic kinases of the AGC group.
