7747-19-5Relevant academic research and scientific papers
Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction
Zhou, Wenjuan,Xu, Chenhao,Dong, Guanjun,Qiao, Hui,Yang, Jing,Liu, Hongmin,Ding, Lina,Sun, Kai,Zhao, Wen
, (2021/03/24)
Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.
Synthesis and evaluation of anti-inflammatory and analgesic activities of new 1,2,4-triazole derivatives
Ahmadi, Fatemeh,Ghayahbashi, Mohsen Rezayan,Sharifzadeh, Mohammad,Alipoiur, Eskandar,Ostad, Seyed Nasser,Vosooghi, Mohsen,Khademi, Hamid Reza,Amini, Mohsen
, p. 69 - 76 (2015/04/14)
In this study, the synthesis, anti-inflammatory and analgesic activities of eight new 5-thioalkyl-1,3-diaryl-1,2,4-triazole derivatives were reported. For the anti-inflammatory study, the carrageenan-induced rat paw edema model was used. The test compounds in 50 mg/kg and 100 mg/kg were injected as IP and paw edema was determined. The results showed that some of the compounds have good activity compared to the references drug, indomethacin. For analgesic activity, the test compounds were studied using the in Tail-flick test model in 50 and 100 mg/kg as IP injections. Their analgesic activities were determined after 30 min via latency time assay. Statistical analysis showed that all test compounds have antinociceptive activity in the range of 24% -47% as compared to the control with a dose of 50 mg/kg. However, all tested compounds have analgesic activity lower than the standard drug, morphine.
Sulfur-carbon bond formation through ring-opening of triazolothiadiazole with organometallics
Othman, Raja Ben,Massip, Stephane,Marchivie, Mathieu,Jarry, Christian,Vercouillie, Johnny,Chalon, Sylvie,Guillaumet, Gerald,Suzenet, Franck,Routier, Sylvain
, p. 3225 - 3231 (2014/06/09)
An efficient and convenient method was developed for the formation of S-substituted thiotriazoles through an unprecedented organometallic addition and subsequent ring-opening sequence of 3-substituted [1,2,4]triazolo[3,4-b][1,3,4] thiadiazole. The method is applicable to a wide range of substrates containing different functional groups and furnishes excellent yields of the corresponding N-unsubstituted 3- or 5-alkyl, aryl, alkynyl and alkenyl sulfanyl-1,2,4-triazole products. Copyright
On the Amination of 1,2,4-Triazines by Potassium Amide in Liquid Ammonia and by Phenyl Phosphorodiamidate. A 15N-study (1)
Rykowski, A.,van der Plas, H. C.
, p. 653 - 656 (2007/10/02)
The amination of 5-R and 6-R-3-X-1,2,4-triazines (R=C6H5, t-C4H9, X=SCH3, SO2CH3, N(1+)(CH3)3, Cl) by potassium amide in liquid ammonia has been studied.In all reactions the formation of the corresponding 3-amino-1,2,4-triazines takes place; in some react
Reactions with N-Acylimino-dithiocarbonic-acid-diesters
Augustin, M.,Richter, M.,Salas, S.
, p. 55 - 68 (2007/10/02)
Reactions of N-acylimino-dithiocarbonic-acid-S,S-diesters 1 with nucleophilic compounds present new possibilities to synthesize heterocycles.With amines 1a reacts by mono- and disubstitution, respectively, of methylthio-groups to isothioureas 2 and guanidines 3, with 1,2-binucleophilic arenes to benzoheterocycles 4, with aliphatic diamines to imidazolines 5, pyrimidines 6, diazepines 7 and the hexamethylene-diamine-derivatives 8. 1a reacts also with hydrazines to 1,2,4-triazoles 9 and with hydrazides to the thiosemicarbazones 10 or 1,3,4-oxadiazoles 11.Heterocyclisations of 1 with guanidines, thiourea, salts of thiourea and amidines give the 1,3,5-triazines 12, 14, 15 and 16.N-benzoyl-dithiocarbonic-acid-methylester -amid reacts with CH-acidic compounds to thiazoles 17.The structures of the final products are determined by i.r.-, 1H-n.m.r.-, u.v.- and mass-spectras.
