137062-87-4Relevant academic research and scientific papers
Optimizing the reversibility of hydrazone formation for dynamic combinatorial chemistry
Nguyen, Regis,Huc, Ivan
, p. 942 - 943 (2003)
Hydrazones from hydrazines bearing electron withdrawing groups, and aromatic or aliphatic aldehydes form and hydrolyse rapidly in water at neutral pH.
Substituent effect of an at-amino group on the H-D exchange of ring hydrogens of adenines compared with an N-methyl group
Wu, Wei,Saga, Tetsuya,Terashima, Isamu,Saeki, Ken-Ichi,Kohda, Kohfuku,Kawazoe, Yutaka
, p. 157 - 162 (1997)
Substituent effects of an N-amino group on the H-D exchange of ring hydrogens of adenines were compared with those of N-methyl group by treating N3-, N7-, and N9-substituted adenines in phosphate buffered D2O media at 70°C. N-Aminoadenines underwent H-D exchange in position 8 faster than the corresponding N-methyladenines. Rates of the exchange of C8-hydrogen of N9-substituted adenines were independent of pD of the medium in an ordinary pD range above their pKa. In strongly alkaline media, N9-aminoadenine underwent H-D exchange at position 2, but N9-methyladenine did not.
Electrophilic amination of adenines. Formation and characteristics of N-aminoadenines
Saga, Tetsuya,Kaiya, Toyo,Asano, Shoji,Kohda, Kohfuku
, p. 219 - 233 (2007/10/03)
Amination of adenine with H2N-O-SO3H in alkaline media afforded 1-, 3-, 7- and 9-aminoadenine isomers at a ratio of about 1:1:3:1. In neutral media, the product ratio of the isomers changed to about 3:1:1:0. These results were different from the regioselectivity obtained by methylation of adenine with dimethyl sulfate under similar conditions. Amination of adenine with dinitrophenoxyamine in DMF gave 1-aminoadenine as the main product and this regioselectivity was also different from that of methylation with CH3I. Chemical characteristics of these N-amino adenines are described.
Pyrrolidine Analogues of 2',3'-Dideoxynucleosides: Synthesis via 9-Aminopurines and 1-Aminopyrimidines
Harnden, Michael R.,Jarvest, Richard L.
, p. 2073 - 2080 (2007/10/02)
Analogues of 2',3'-dideoxynucleosides in which the tetrahydrofuran ring is replaced by a pyrrolidine ring linked to the base through an N-N bond have been prepared.The adenine 26, guanine 25 and and hypoxanthine 27 compounds were synthesised via 9-aminopurines.Corresponding derivatives of 5-iodouracil 31, 5-chlorouracil 33 and 5-chlorocytosine 35 were prepared by substitution at the 5-position of hydroxy protected uracil derivatives.Enantiomers, 40a and 40b, of the pyrrolidine analogue of dideoxycytidine were prepared from 1-aminocytosine.The novel N-aminobases 9-aminoadenine 10, 1-aminocytosine 13 and 1-aminothymine 15 are described.
