56050-99-8Relevant academic research and scientific papers
Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
supporting information, p. 10907 - 10912 (2019/08/02)
Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.
Novel Symmetrical Benzazolyl Derivatives Endowed with Potent Anti-Heparanase Activity
Messore, Antonella,Madia, Valentina Noemi,Pescatori, Luca,Saccoliti, Francesco,Tudino, Valeria,De Leo, Alessandro,Bortolami, Martina,De Vita, Daniela,Scipione, Luigi,Pepi, Federico,Costi, Roberta,Rivara, Silvia,Scalvini, Laura,Mor, Marco,Ferrara, Fabiana Fosca,Pavoni, Emiliano,Roscilli, Giuseppe,Cassinelli, Giuliana,Milazzo, Ferdinando M.,Battistuzzi, Gianfranco,Di Santo, Roberto,Giannini, Giuseppe
, p. 10834 - 10859 (2019/01/03)
Heparanase is the only mammalian endo-β-d-glucuronidase involved in a variety of major diseases. The up-regulation of heparanase expression increases tumor size, angiogenesis, and metastasis, representing a validated target in the anti-cancer field. To date, only a few small-molecule inhibitors have been described, but none have gotten through pre-clinical development. Previously, we explored 2-(4-(4-(bromo-methoxybenzamido)benzylamino)phenyl) benzazole derivatives as anti-heparanase agents, proposing this scaffold for development of broadly effective heparanase inhibitors. Herein, we report an extended investigation of new symmetrical 2-aminophenyl-benzazolyl-5-acetate derivatives, proving that symmetrical compounds are more effective than asymmetrical analogues, with the most-potent compound, 7g, being active at nanomolar concentration against heparanase. Molecular docking studies were performed on the best-acting compounds 5c and 7g to rationalize their interaction with the enzyme. Moreover, invasion assay confirmed the anti-metastatic potential of compounds 5c, 7a, and 7g, proving the inhibition of the expression of proangiogenic factors in tumor cells.
Effective approach to ureas through organocatalyzed one-pot process
Wang, Mingliang,Han, Jilai,Si, Xiaojia,Hu, Yimin,Zhu, Jidong,Sun, Xun
supporting information, p. 1614 - 1618 (2018/03/28)
An efficient approach to N, N′-unsymmetrically substituted ureas 9 has been developed through the ammonolysis process of N-Boc protected anilines 7 with amines prompted by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Moreover, a convenient protocol for the
Synthesis of symmetrical ureas by (Diacetoxyiodo)benzene-induced hofmann rearrangement
Landsberg, Dirk,Kalesse, Markus
experimental part, p. 1104 - 1106 (2010/06/19)
Amides undergo Hofmann rearrangement by treatment with (diacetoxyiodo) benzene (DAIB) to provide symmetrical ureas in a simple and robust transformation. Georg Thieme Verlag Stuttgart - New York.
