Synthesis of 1,2,3-Triazole Derivatives and Evaluation of their Anticancer Activity

Anticancer screening of several 1,2,3-triazoles with heterocyclic fragments has been performed. The 1,2,3-triazole derivatives were synthesized from available starting materials according to convenient synthetic procedures. The antitumor activity of the synthesized compounds was tested in vitro by the National Cancer Institute in NCI60 cell lines. It was observed that some compounds showed slight anticancer activity. One of them possessed a moderate activity against melanoma, colon, and breast cancer. Standard COMPARE analysis was performed at the GI50 level

New cascade reaction of azides with malononitrile dimer to polyfunctional [1,2,3]triazolo[4,5-<i>b</i>]pyridine

<p>A new cascade reaction of azides with malononitrile dimer yielding polyfunctional [1,2,3]triazolo[4,5-<i>b</i>]pyridine was found. It was established that during the reaction of aryl azides with malononitrile dimer, under base catalysis, the formed intermediate triazole underwent spontaneous cyclization leading to the pyridine ring annulation. The obtained products have provided a new entry to [1,2,3]triazolo[4,5-<i>b</i>]pyridine.</p

Anticancer Activity Evaluation of New Thieno[2,3-d]pyrimidin-4(3H)-ones and Thieno[3,2-d]pyrimidin-4(3H)-one Derivatives

Anticancer screening of several novel thienopyrimidines has been performed. The thienopyrimidine derivatives were synthesized from available starting materials according to the convenient synthetic procedures using a one-pot solvent-free reaction which gave a wide access to thienopyrimidine-derivative production. The synthesized compounds were preselected via molecular docking to be tested for their anticancer activity in NCI 60 cell lines. It was observed that some compounds showed remarkable anticancer activity. It was found that the most active compound among thieno[2,3-d]pyrimidine-4(3H)-ones is 2-(benzylamino)-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one, which possesses cytotoxic activity on almost all cancer cell lines with mean growth 51.01%, where the most sensitive was the melanoma cell line MDA-MB-435 with GP (Growth Percent) = &minus;31.02%. The patterns of structure&ndash;activity that are important for further optimization of the structure and the creation of more selective and active anticancer agents were proposed

Facile and Efficient One-Pot Procedure for Thieno[2,3-<i>e</i>][1,2,3]triazolo[1,5-<i>a</i>]pyrimidines Preparation

<div><p></p><p>Base-catalyzed cycloaddition reactions of heterocyclic azides with activated nitriles were studied. Convenient, efficient, and high-yield synthetic method for thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines preparation from available starting reagents without complicated protocols was elaborated. Such an approach allows creation of broad combinatorial libraries for drug discovery.</p> <p>[Supplementary materials are available for this article. Go to the publisher's online edition of <i>Synthetic Communications</i>® for the following free supplemental resource(s): Full experimental and spectral details.]</p> </div

New Convenient Strategy for Annulation of Pyrimidines to Thiophenes or Furans via the One-pot Multistep Cascade Reaction of 1<i>H</i>‑Tetrazoles with Aliphatic Amines

A versatile, convenient, efficient and high-yield synthetic method for 2-R³,R⁴-amino-5-R¹-6-R²-thieno­[2,3-<i>d</i>]­pyrimidin-4­(3<i>H</i>)-ones, 2-R³,R⁴-amino-5-R¹-6-R²-thieno­[3,2-<i>d</i>]­pyrimidin-4­(3<i>H</i>)-ones, and benzofuro­[3,2-<i>d</i>]­pyrimidin-4­(3<i>H</i>)-ones preparation has been developed. The reaction proceeded without using solvents and included several steps. A variety of thieno­[2,3-<i>d</i>]­pyrimidine and thieno­[3,2-<i>d</i>]­pyrimidine derivatives with substituents of different nature were obtained in high yields from substituted alkyl 2-(1<i>H</i>-tetrazol-1-yl)­thiophene-3-carboxylates, 3-(1<i>H</i>-tetrazol-1-yl)­thiophene-2-carboxylates, and 3-(1<i>H</i>-tetrazol-1-yl)­benzofuran-2-carboxylate after their treatment with aliphatic amines

Facile synthetic route to benzo[<i>c</i>]chromenones and thieno[2,3-<i>c</i>]chromenones

<p>Convenient two-step procedure for the synthesis of fused chromenone derivatives was developed. Reduction of the obtained in the Meerwein arylation reaction aryl- and thienylquinones allowed to construct 6<i>H</i>-benzo[<i>c</i>]chromene-6-ones and 4<i>H</i>-thieno[2,3-<i>c</i>]chromen-4-one in a more cost- and time-effective manner in comparison with already known methods. The obtained products have provided a new entry to chromenone derivatives.</p