1477-24-3Relevant articles and documents
Synthesis and Intramolecular Heterocyclization of Selected Isonicotinic Acid Thiocarbazides
Nurkenov,Karipova, G. Zh.,Seilkhanov,Satpaeva, Zh. B.,Fazylov,Nukhuly
, p. 1923 - 1926 (2019)
The reaction of isonicotinic acid hydrazide with ethyl-, allyl-, and cinnamoyl isothiocyanates has afforded the corresponding alkylthiosemicarbazides and the products of their intramolecular heterocyclization, 1,2,4-triazoles.
Reactivity of N1-dithioester substituted pyridinand pyrazincarboxamidrazones
Orlewska, Czeslawa,Pancechowska-Ksepko, Danuta,Foks, Henryk,Zwolska, Zofia,Augustynowicz-Kopec, Ewa
, p. 737 - 744 (2006)
The N1-dithioester substituted pyridin- and pyrazincarboxamidrazones underwent cyclocondensation to 5-methylsulfanyl-1,3,4- thiadiazole or 1,2,4-triazole derivatives, depending on the reaction conditions. With an excess of secondary amines, pyrazincarboxamidrazone dithioester gave 5-amino-1,3,4-thiadiazoles and with an ethanoloamine a 1,2,4-triazole derivative. Prepared compounds were evaluated as potential tuberculostatic agents, but the minimum inhibitory concentrations values indicated no significant activity. Copyright Taylor & Francis Group, LLC.
Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X
Fonovi?, Ur?a Pe?ar,Gobec, Stanislav,Hrast, Martina,Knez, Damijan,Kos, Janko,Proj, Matic,Zidar, Nace
, (2020/03/24)
Cathepsin X is a cysteine carboxypeptidase that is involved in various physiological and pathological processes. In particular, highly elevated expression and activity of cathepsin X has been observed in cancers and neurodegenerative diseases. Previously, we identified compound Z9 (1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-one) as a potent and specific reversible cathepsin X inhibitor. Here, we have explored the effects of chemical variations to Z9 of either benzodioxine or triazol moieties, and the importance of the central ketomethylenethio linker. The ketomethylenethio linker was crucial for cathepsin X inhibition, whereas changes of the triazole heterocycle did not alter the inhibitory potencies to a greater extent. Replacement of benzodioxine moiety with substituted benzenes reduced cathepsin X inhibition. Overall, several synthesized compounds showed similar or improved inhibitory potencies against cathepsin X compared to Z9, with IC50 values of 7.1 μM–13.6 μM. Additionally, 25 inhibited prostate cancer cell migration by 21%, which is under the control of cathepsin X.