Antimicrobial activity of new benzazolyl N-sulfonyl amidines

Galieva, Nadezhda A.; Saveliev, D.; Eltsov, Oleg S.; Бакулев, В. А.; Lübec, Gert; Xing, Jihong; Fan, Zhijin; Beryozkina, Tetyana

doi:10.1016/j.mencom.2021.07.019

Cited by 10 publications

(1 citation statement)

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“…It is also known that the introduction of the N -sulfonylamidine group into molecules of different classes of biologically active compounds increases their activity. Thus, for example, camptothecin bearing the N -sulfonylamidine group is a powerful inhibitor of topoisomerase and decreases the growth of various forms of cancer . Antimicrobal activity of benzazolyl N -sulfonyl amidines was found…”

Section: Introductionmentioning

confidence: 99%

Tandem Cycloaddition of Azides to 3,3-Diaminoacrylonitriles (2-Cyanoacetamidines) and Cornforth-Type Rearrangement as an Approach to 5-Amino-1,2,3-triazole-4-N-substituted Imidamides

et al. 2023

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An efficient base-catalyzed, metal-free method for the synthesis of 5-amino-1,2,3-triazole-4-N-sulfonyl-and arylimidamides, directed by the structure of the amidine group, has been developed. It is based on a previously unknown tandem process involving cycloaddition reaction to 3,3diaminoacrylonitriles (2-cyanoacetamidines) with aryl(alkyl)sulfonyl or aryl azides and Cornforth-type rearrangement. During the reaction optimization, different factors were found to facilitate the title reaction, which include the use of a strong base and N-mono-or N,N′-disubstituted 3,3-diaminoacrylonitriles. The reaction is tolerant to variously N-monosubstituted and N,N′-disubstituted 3,3-diaminoacrylonitriles and to various aryland aryl/alkyl sulfonyl azides. The developed method has a broad scope and can be applied to obtain a variety of 5-amino-1,2,3triazole-4-carbimidamides bearing at the N 1 position alkyl, allyl, propargyl, benzyl, cycloalkyl, and heteroaryl substituents and sulfonyl and aryl substituents at the amidine group. Post-cyclization reactions of prepared 5-amino-1,2,3-triazoles with DMF-DMA DMA-DMF leads to 1,2,3-triazolo [4,5-d]pyrimidines, 8-aza purine analogues demonstrating the applicability of the prepared compounds in organic synthesis.

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Section: Introductionmentioning

confidence: 99%