536760-31-3Relevant academic research and scientific papers
4—(1H— IMIDAZOL— 5— YL) -1H-PYRROLO [2, 3-B] PYRIDINES FOR USE IN THE TREATMENT OF LEUKAEMIAS, LYMPHOMAS AND SOLID TUMORS
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, (2019/10/23)
The present invention relates to novel 4-(1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine compounds which are useful in the treatment of lymphomas, leukaemias, and solid tumors.
Metal-mediated base pairing in DNA involving the artificial nucleobase imidazole-4-carboxylate
Sandmann, Nikolas,Defayay, Denise,Hepp, Alexander,Müller, Jens
, p. 85 - 93 (2018/11/26)
The use of imidazole-4-carboxylate (X) as an artificial nucleobase in metal-mediated base pairing is reported. Towards this end, the corresponding deoxyribonucleoside was synthesized and structurally characterized as its sodium salt (sodium 1,2-dideoxy-1-(4-carboxyimidazol-1-yl)-D-ribofuranose). The deoxyribonucleoside was incorporated into different DNA duplexes (parallel-stranded and antiparallel-stranded), and their Cu(II)- and Ag(I)-binding behavior was investigated. It was shown that both X–Cu(II)–X and X–Ag(I)–X base pairs can be formed, with the former being more stabilizing than the latter. The formation of an X–Cu(II)–X base pair is accompanied by an increase in the duplex melting temperature of approximately 20 °C for antiparallel-stranded duplexes and of 12 °C for the parallel-stranded duplex under investigation. Imidazole-4-carboxylate represents the first imidazole-based nucleoside for Cu(II)-mediated base pairing. Moreover, it is the smallest nucleoside known to form stable Cu(II)-mediated base pairs. Structures of the X–Cu(II)–X and X–Ag(I)–X base pairs are proposed, too, based on molecular structures obtained using the model nucleobase 1-benzyl-1H-imidazole-4-carboxylate.
Preparation and diels-alder chemistry of 4-vinylimidazoles
Lovely, Carl J.,Du, Hongwang,Sivappa, Rasapalli,Bhandari, Manojkumar R.,He, Yong,Dias, H. V. Rasika
, p. 3741 - 3749 (2008/02/04)
(Chemical Equation Presented) Various 4-vinylimidazole derivatives have been prepared from the corresponding 4-iodoimidazoles or from urocanic acid. Several methods for the elaboration of these vinylimidazoles and their Diels-Alder reactions are reported. All of the vinylimidazoles prepared in the course of this study react with N-phenylmaleimide quite readily with mild thermal activation providing a single cycloadduct, in most cases the initial, nonaromatic adduct. With more electron rich substrates, there is a tendency for these initial cycloadducts to undergo aromatization, ene reaction, and oxidation although this can be circumvented to a large extent by the choice of reaction conditions. Limited reactions were observed with other dienophiles, providing the expected cycloadducts in most cases, although an abnormal adduct was obtained in one case with dimethyl acetylene dicarboxylate. These substrates also participate in regioselective Diels-Alder reactions with monoactivated dienophiles, but require fairly forcing conditions, thus only providing the aromatized cycloadducts in modest yields. An investigation of substituent effects at the 2-position of the imidazole moiety was undertaken, in which electron-donating and weakly electron-withdrawing substituents are tolerated. In addition, several substrates with terminally substituted vinyl moieties have been investigated.
Regioselective synthesis of 1-benzyl- and 1-methyl-4- vinylimidazole and their reactions with N-phenylmaleimide
Lovely, Carl J.,Du, Hongwang,Rasika Dias
, p. 1 - 7 (2007/10/03)
The regioselective synthesis of 1-benzyl- and 1-methyl-4- vinylimidazole from 4,5-diiodoimidazole is described. Their Diels-Alder reactions with N-phenylmaleimide provide a variety of adducts, including the anticipated enamine and the corresponding aromatized isomer. However, additional products including ene adducts, a bis Diels-Alder adduct and oxidation products were isolated.
