4546-74-1Relevant academic research and scientific papers
Replacement of canonical DNA nucleobases by benzotriazole and 1,2,3-triazolo[4,5-d]pyrimidine: Synthesis, fluorescence, and ambiguous base pairing
Seela, Frank,Jawalekar, Anup M.,Muenster, Ingo
, p. 751 - 765 (2007/10/03)
The syntheses and the fluorescence properties of 7H-3,6-dihydro-1,2,3- triazolo[4,5-d]pyrimidin-7-one 2′-deoxy-β-D-ribonucleosides (=2′-deoxy-8-azainosine) 3 (N3), 15 (N2), and 16 (N1) as well as of 1,2,3-benzotriazole 2′-O-methyl-β- or -α-D-ribofuranosides 6 (N1) and 24 (N1) are described. Also the fluorescence properties of 1,2,3-benzotriazole 2′-deoxy-β-D-ribofuranosides 4 (N1) and 5 (N2) are evaluated. From the nucleosides 3-6, the phosphoramidites 19, 26a, 26b, and 28 are prepared and employed in solid-phase oligonucleotide synthesis. In 12-mer DNA duplexes, compound 3 shows similar ambiguous base-pairing properties as 2′-deoxyinosine (1), while the nucleosides 4-6 show strong pairing with each other and discriminate very little the four canonical DNA constituents.
Synthesis and anti-HIV evaluation of 2',3'-dideoxy imidazo- and ν- triazolo[4,5-d]pyridazine nucleosides
Bussolari, Jacqueline C.,Panzica, Raymond P.
, p. 2373 - 2379 (2007/10/03)
The syntheses of the 2'-deoxy and 2',3'-dideoxynucleosides of 2,8-diaza- 3-deazainosine and the 2',3'-dideoxynucleoside of 2-aza-3-deazainosine were achieved and the pathways leading to these novel nucleosides are described. The preparation of the 2',3'-dideoxynucleoside (1) of 2-aza-3-deazainosine involved deoxygenation of the 2'-deoxy-3'-imidazolide intermediate with n- Bu3SnH and AIBN. The latter nucleoside was synthesized from the known 2'- deoxy derivative of 2-aza-3-deazainosine. The three-step synthesis of 1 from the 2'-deoxy analogue was accomplished in 40% overall yield. Rather than synthesize the corresponding 2',3'-dideoxynucleoside (2) of 2,8-diaza-3- deazainosine in the same manner, i.e. deoxygenation of the 2'- deoxynucleoside, a more cost-effective route was chosen. This pathway involved reductive cleavage of the 5'-protected, 2',3'-thiocarbonate derivative to furnish a mixture of the 2'- and 3'-deoxy isomers. This mixture was not separated, but was deoxygenated by the aforementioned imidazolide method. Using this methodology, 2 was prepared in 23% overall yield from 2,8- diaza-3-deazainosine. Nucleosides 1 and 2 were evaluated for antiretroviral activity and were found to be inactive. (C) 1999 Elsevier Science Ltd.
