“…Among others, anti-inflammatory [37–38], antiviral [28,39] and antidiabetic [40] effects should be mentioned, besides the non-negligible cancer cell growth-inhibitory features of the corresponding compounds [30,34,41–42]. …”
Summary5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke–Blackburn–Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe an operationally simple, one-pot two-step GBB protocol for the rapid construction of a 46 membered imidazo[1,2-b]pyrazole library with yields up to 83%.
“…Among others, anti-inflammatory [37–38], antiviral [28,39] and antidiabetic [40] effects should be mentioned, besides the non-negligible cancer cell growth-inhibitory features of the corresponding compounds [30,34,41–42]. …”
Summary5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke–Blackburn–Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe an operationally simple, one-pot two-step GBB protocol for the rapid construction of a 46 membered imidazo[1,2-b]pyrazole library with yields up to 83%.
“…Imidazopyrazoles, as unusual fused heterocyclic compounds, are attractive compounds for drug discovery because many compounds incorporating these scaffolds exhibit a wide range of biological, medicinal, and pharmaceutical activities, including antitumor activities, 4 anti-inflammatory activities, 5 antiviral activity against herpes simplex virus type 1, 6 and antineoplastic activity against L1210 leukemia cells. 7 In addition, some compounds of this class show inhibitory effects on deoxyribonucleic acid synthesis, 8 MAP kinase, 5 L1220 tumor-derived ribonucleotide reductase, 9 and ribonucleoside diphosphate reductase, 10 as well as synchronization of human lymphoid cells and HeLa cells.…”
mentioning
confidence: 99%
“…Moreover, we found that the presence of an acidic catalyst was essential to obtain a high yield. Next, we attempted to identify the optimal catalyst by screening 0.1 mmol quantities of a number of Lewis or Brønsted acids (Table 2, entries [1][2][3][4][5][6][7][8][9][10][11][12]. The experiments showed that the highest yields were obtained with 4-toluenesulfonic acid.…”
mentioning
confidence: 99%
“…7 In addition, some compounds of this class show inhibitory effects on deoxyribonucleic acid synthesis, 8 MAP kinase, 5 L1220 tumor-derived ribonucleotide reductase, 9 and ribonucleoside diphosphate reductase, 10 as well as synchronization of human lymphoid cells and HeLa cells. [11][12] Recently, other members of this group of compounds have been shown to be useful as nonsteroidal agonists and antagonists of the androgen receptor modulators that are useful in the treatment of a variety of diseases.…”
An efficient method has been developed for the synthesis of a novel series of N-alkyl-2-aryl-5H-imidazo [1,2-b]pyrazol-3-amines in good-to-high yields by the three-component condensation of an aromatic aldehyde, an aminopyrazole, and an isocyanide in acetonitrile with 4-toluenesulfonic acid as a catalyst at room temperature.
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