Pyrido[2’,3’:4,5]pyrrolo[2,1-d][1,2,3,5]tetrazine-4(3H)-ones, a new class of temozolomide heteroanalogues

The Medicinal Chemistry of Imidazotetrazine Prodrugs

“…It is worthy of note that coupling with isocyanates was found to elicit higher yields when performed under microwave irradiation with greatly reduced reaction times ( Scheme 20 ). Three of the compounds 62 showed growth inhibitory activity against a limited number of cell lines [ 72 ], but none of the compounds 61 tested in the NCI60 panel showed any significant activity [ 73 ].…”

A new class of unique quinoidal-like imidazoliumyl tetrazinides: synthesis, structure, and mechanism

“…The derivatives of 1,2,3,5-tetrazinone, and in particular azolo-tetrazinones, have been extensively studied over the last two decades for their outstanding antitumor properties. 14,[17][18][19][20][21][22][23] 1,2,4,5-Tetrazinone is characterized by its electron deficiency and single electron transfer, and it easily forms oxoverdazyl radicals (Fig. 1(b)), 24,25 which are a kind of important persistent free radicals under normal conditions.…”

One-Pot Synthesis of 2-Amino-indole-3-carboxamide and Analogous

“…Herein, we would like to report a novel, straightforward, and one-pot synthesis of highly substituted 2-amino (hetero)-indole-3-carboxamides. 2-Amino-indole-3- carboxamides in the past have been synthesized by several step processes, for example, by [3,3]-sigmatropic rearrangement and intramololecular cyclization from N -arylhydroxamic acids and malononitrile, by nucleophilic aromatic substitution reaction with malondinitrile or cyanoaceticacid esters, followed by reduction (eq 1, Scheme ), − or by a four-component reaction of pyridine or 3-picoline, chloroacetonitrile, malononitrile, and aromatic aldehydes, by the Nenitzescu reaction of primary ketene aminals and 1,4-benzoquinones, by the reaction of 2-haloanilines and substituted acetonitriles, − and other methods . Our synthetic approach involves a nucleophilic aromatic substitution reaction of a suitable o -halo-nitro-(hetero)aromate with a cyanoacetamide and a subsequent reductive cyclization.…”