40288-36-6Relevant academic research and scientific papers
Design, Synthesis and Discovery of N,N’-Carbazoyl-aryl-urea Inhibitors of Zika NS5 Methyltransferase and Virus Replication
Spizzichino, Sharon,Mattedi, Giulio,Lauder, Kate,Valle, Coralie,Aouadi, Wahiba,Canard, Bruno,Decroly, Etienne,Kaptein, Suzanne J. F.,Neyts, Johan,Graham, Carl,Sule, Zakary,Barlow, David J.,Silvestri, Romano,Castagnolo, Daniele
supporting information, p. 385 - 390 (2020/01/24)
The recent outbreaks of Zika virus (ZIKV) infection worldwide make the discovery of novel antivirals against flaviviruses a research priority. This work describes the identification of novel inhibitors of ZIKV through a structure-based virtual screening approach using the ZIKV NS5-MTase. A novel series of molecules with a carbazoyl-aryl-urea structure has been discovered and a library of analogues has been synthesized. The new compounds inhibit ZIKV MTase with IC50 between 23–48 μM. In addition, carbazoyl-aryl-ureas also proved to inhibit ZIKV replication activity at micromolar concentration.
Synthesis and molecular docking of N,N′-disubstituted thiourea derivatives as novel aromatase inhibitors
Pingaew, Ratchanok,Prachayasittikul, Veda,Anuwongcharoen, Nuttapat,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
, p. 171 - 178 (2018/05/22)
A three series of thioureas, monothiourea type I (4a–g), 1,4-bisthiourea type II (5a–h) and 1,3-bisthiourea type III (6a–h) were synthesized. Their aromatase inhibitory activities have been evaluated. Interestingly, eight thiourea derivatives (4e, 5f–h, 6d, 6f–h) exhibited the aromatase inhibitory activities with IC50 range of 0.6–10.2 μM. The meta-bisthiourea bearing 4-NO2 group (6f) and 3,5-diCF3 groups (6h) were shown to be the most potent compounds with sub-micromolar IC50 values of 0.8 and 0.6 μM, respectively. Molecular docking also revealed that one of the thiourea moieties of these two compounds could mimic steroidal backbone of the natural androstenedione (ASD) via hydrophobic interactions with enzyme residues (Val370, Leu477, Thr310, and Phe221 for 6f, Val370, Leu477, Ser478, and Ile133 for 6h). This is the first time that the bisthioureas have been reported for their potential to be developed as aromatase inhibitors, in which the 4-NO2 and 3,5-diCF3 analogs have been highlighted as promising candidates.
Ph3P/I2-mediated synthesis of N,N′,N″-substituted guanidines and 2-iminoimidazolin-4-ones from aryl isothiocyanates
Wangngae, Sirilak,Pattarawarapan, Mookda,Phakhodee, Wong
, p. 10331 - 10340 (2018/05/31)
A convenient one-pot procedure for the synthesis of acyclic and cyclic guanidines mediated by the Ph3P/I2 system is described. Sequential condensation of aryl isothiocyanates with amines followed by dehydrosulfurization and guanylation could lead to both symmetric and unsymmetric N,N′,N″-substituted derivatives. Through a tandem guanylation-cyclization, a series of 2-iminoimidazolin-4-ones could also be prepared in good yields from the reaction of aryl isothiocyanates with amino acid methyl esters.
Convenient synthesis of unsymmetrical N,N′-disubstituted thioureas in water
Li, Zhengyi,Chen, Yuan,Yin, Yue,Wang, Zhiming,Sun, Xiaoqiang
, p. 670 - 673 (2016/11/18)
A simple and convenient two-step method has been developed and used to synthesise 25 (4 of which are novel) unsymmetrical N,N′-disubstituted thioureas in water. Alkylamines or variously substituted arylamines reacted smoothly with phenyl chlorothionoformate at room temperature to form thiocarbamates, which were then reacted with another alkyl- or arylamine in water at reflux to afford the unsymmetrical N,N′-disubstituted thioureas in good to excellent yields. Mild conditions, simple work-up, high yields as well as using water as solvent are the major advantages of the method.
Powerful approach to heterocyclic skeletal diversity by sequential three-component reaction of amines, isothiocyanates, and 1,2-diaza-1,3-dienes
Attanasi, Orazio A.,Bartoccini, Silvia,Favi, Gianfranco,Giorgi, Gianluca,Perrulli, Francesca Romana,Santeusanio, Stefania
experimental part, p. 1161 - 1167 (2012/03/12)
By highly efficient, one-pot, three-component reactions, combining one set of 1,2-diaza-1,3-dienes (DDs), primary amines, and isothiocyanates in a different sequential order of addition, heterocyclic skeletal diversity can be achieved. The key feature dis
