16754-81-7Relevant academic research and scientific papers
Synthesis, cytostatic, antimicrobial, and anti-HCV activity of 6-substituted 7-(het)aryl-7-deazapurine ribonucleosides
Nau?, Petr,Caletková, Olga,Kone?ny, Petr,D?ubák, Petr,Bogdanová, Kate?ina,Kolá?, Milan,Vrbková, Jana,Slavětínská, Lenka,Tlou?t'Ová, Eva,Perlíková, Pavla,Hajdúch, Marián,Hocek, Michal
, p. 1097 - 1110 (2014/03/21)
A series of 80 7-(het)aryl- and 7-ethynyl-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were
Structural determinants for N1/N7 cyclization of nicotinamide hypoxanthine 5′-dinucleotide (NHD+) derivatives by ADP-ribosyl cyclase from Aplysia californica: Ca2+-mobilizing activity of 8-substituted cyclic inosine 5′-diphosphoribose analogues in T-lymphocytes
Moreau, Christelle,Wagner, Gerd K.,Weber, Karin,Guse, Andreas H.,Potter, Barry V. L.
, p. 5162 - 5176 (2008/04/18)
A series of nicotinamide hypoxanthine 5′-dinucleotide (NHD +) analogues modified at C-8 (2-5) and 7-deaza-NHD+ were synthesized, and cyclization in the presence of Aplysia ADP-ribosyl cyclase was studied. All 8-substituted NHD+ analogues were converted into their N1-cyclic forms by the enzyme, while in contrast, 7-deaza-NHD+ 17 was hydrolyzed into 7-deazainosine 5′-diphosphoribose (7-deaza-IDPR) 25. Correlations are made showing that the conformation of the NHD+ substrate is the key to successful cyclization. The pharmacological activities of these novel cIDPR derivatives were evaluated in both permeabilized and intact Jurkat T-lymphocytes. The results show that in permeabilized cells both 8-iodo 1g and 8-N3-N1-cIDPR 1d have an activity comparable to that of cADPR, while 8-iodo 1g and 8-phenyl-N1-cIDPR 1c have a small but significant effect in intact cells and can therefore be regarded as membrane-permeant; thus, cIDPR derivatives are emerging as important novel biological tools to study cADPR-mediated Ca2+ release in T-cells.
Nucleic acid related compounds. 86. Nucleophilic functionalization of adenine, adenosine, tubercidin, and formycin derivatives via elaboration of the heterocyclic amino group into a readily displaced 1,2,4-triazol-4-yl substituent
Miles, Robert W.,Samano, Vicente,Robins, Morris J.
, p. 5951 - 5957 (2007/10/02)
Treatment of 9-methyladenine and hydroxyl-protected derivatives of adenosine and 2′-deoxyadenosine with 1,2-bis[(dimethylamino)methylene]hydrazine and/or its dihydrochloride at elevated temperatures in appropriate solvents resulted in elaboration of the 6-amino group into a 6-(1,2,4-triazol-4-yl) substituent in excellent yields. Analogous functionalization of the amino groups of tubercidin {4-amino-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]-pyrimidine} and formycin {7-amino-3-(β-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidine} gave the respective 4- and 7-(1,2,4-triazol-4-yl) derivatives. Nucleophilic replacement of the triazole moiety gave the respective 6-, 4-, and 7-substituted purine, pyrrolo[2,3-d]pyrimidine, and pyrazolo[4,3-d]pyrimidine products. This first general method for "direct" nucleophilic replacement of an amino group on these nitrogen heterocycles also provides a new class of compounds for potential postsynthetic modifications after incorporation into oligonucleotides.
