83236-48-0Relevant academic research and scientific papers
4-Arylthieno[2,3-b]pyridine-2-carboxamides Are a New Class of Antiplasmodial Agents
Alder, Arne,Gilberger, Tim,Kunick, Conrad,Schwed, Sandra I.
, (2020/08/24)
Malaria causes hundreds of thousands of deaths every year, making it one of the most dangerous infectious diseases worldwide. Because the pathogens have developed resistance against most of the established anti-malarial drugs, new antiplasmodial agents are urgently needed. In analogy to similar antiplasmodial ketones, 4-arylthieno[2,3-b]pyridine-2-carboxamides were synthesized by Thorpe-Ziegler reactions. In contrast to the related ketones, these carboxamides are only weak inhibitors of the plasmodial enzyme PfGSK-3 but the compounds nevertheless show strong antiparasitic activity. The most potent representatives inhibit the pathogens with IC50values in the two-digit nanomolar range and exhibit high selectivity indices (>100).
Cross-recyclization of 4-aryl-2,6-diamino-4H-thiopyran-3,5-dicarbonitriles with 1-morpholino-1-cyclopentene: New route to 4-aryl-2-thioxo-2,5,6,7- tetrahydro-1H-[1]pyrindine-3-carbonitriles and their derivatives
Dyachenko,Dyachenko
, p. 280 - 285 (2007/10/03)
Reaction of 4-aryl-2,6-diamino-4H-thiopyran-3,5-dicarbonitriles with 1-morpholino-1-cyclopentene led to the formation of 4-aryl-2-thioxo-2,5,6,7- tetrahydro-1H-[1]pyrindine-3-carbonitriles used in the synthesis of substituted 2-alkylsulfanyl-4-aryl-6,7-di
Synthesis, reactions and antimicrobial activity of new cyclopenta[e]thieno-[2,3-b]pyridines and related heterocyclic systems
Bakhite,Abdel-Rahman,Mohamed,Thabet
, p. 577 - 583 (2007/10/03)
Reaction of the arylidene cyanothioacetamides la, b with cyclopentanone was proved to give a mixture of 4-aryl-3-cyanocyclopenta[b]pyridine-2(1H)-thiones 2a, b and the corresponding 7-arylidene derivatives 3a, b. Compounds 2a, b were reacted with ethyl chloroacetate or chloroacetamide to give the promising S-substituted thiopyridines 6a-d. On treatment of the latter compounds with sodium ethoxide in boiling ethanol, they underwent intramolecular Thorpe-Ziegler cyclization to yield the corresponding 3-amino-4-aryl-2-functionalized-cyclopenta[e]thieno[2,3-b]pyridines (7a-d). Most of these thienopyridines were reacted with a variety of reagents to produce other new cyclopentathienopyridines as well as numerous of their condensed heterocyclic derivatives. Some of the compounds synthesized were tested in vitro for their antibacterial and antifungal activity.
CYCLIZATION OF NITRILES. XXXIV. TRANSFORMATION OF 4-ARYL-2,6-DIAMINO-3,5-DICYANO-4H-THIOPYRANS INTO SUBSTITUTED 4-ARYL-3-CYANO-2(1H)-PYRIDINETHIONES AND 2-AMINO-4-ARYL-7,7-DIMETHYL-5-OXO-3-CYANO-5,6,7,8-TETRAHYDRO-4H-BENZOPYRANS
Sharanin, Yu. A.,Shestopalov, A. M.
, p. 1196 - 1200 (2007/10/02)
The reaction of 2,6-diamino-3,5-dicyano-4H-thiopyrans with monocarbonyl and acyclic 1,3-dicarbonyl compounds leads to the elimination of malononitrile and the formation of substituted 4-aryl-3-cyano-2(1H)-pyridinethiones.The reaction with 1,3-cycloalkanediones leads to the elimination of cyanothioacetamide and the formation of 2-amino-4-aryl-3-cyano-4H-benzopyrans.
CYCLIZATION OF NITRILES. X. ENAMINO NITRILES OF THE 1,3-DITHIA-4-CYCLOHEXENE SERIES AND THEIR RECYCLIZATION TO DERIVATIVES OF PYRIDINE AND THIAZOLE
Sharanin, Yu. K.,Shestopalov, A. M.,Promonenkov, V. K.,Rodinovskaya, L. A.
, p. 1402 - 1415 (2007/10/02)
The recyclization of 4-amino-6-aryl-5-cyano-2-cyclopentane(cyclohexane)spiro-1,3-dithia-4-cyclohexenes, obtained from gem-dithiols and arylidenemalononitriles, leads to the formation of 4-aryl-5,6-polymethylene-3-cyano-2-(1H)-pyridinethiones.The latter are used in the synthesis of various 3-aminothienopyridines, 4-aryl-3-amino-5,6,7,8-tetrahydrothienoquinolines, and other heterocyclic compounds condensed with quinoline. 1-Cyano-1-(4-aryl-2-thiazolyl)-2-arylethylenes were obtained by the reaction of the 1,3-dithia-4-cyclohexenes with phenacyl bromides.
