4800-34-4Relevant academic research and scientific papers
Rational design of agonists for bitter taste receptor TAS2R14: from modeling to bench and back
Di Pizio, Antonella,Waterloo, Lukas A. W.,Brox, Regine,L?ber, Stefan,Weikert, Dorothee,Behrens, Maik,Gmeiner, Peter,Niv, Masha Y.
, p. 531 - 542 (2019/07/03)
Human bitter taste receptors (TAS2Rs) are a subfamily of 25 G protein-coupled receptors that mediate bitter taste perception. TAS2R14 is the most broadly tuned bitter taste receptor, recognizing a range of chemically diverse agonists with micromolar-range potency. The receptor is expressed in several extra-oral tissues and is suggested to have physiological roles related to innate immune responses, male fertility, and cancer. Higher potency ligands are needed to investigate TAS2R14 function and to modulate it for future clinical applications. Here, a structure-based modeling approach is described for the design of TAS2R14 agonists beginning from flufenamic acid, an approved non-steroidal anti-inflammatory analgesic that activates TAS2R14 at sub-micromolar concentrations. Structure-based molecular modeling was integrated with experimental data to design new TAS2R14 agonists. Subsequent chemical synthesis and in vitro profiling resulted in new TAS2R14 agonists with improved potency compared to the lead. The integrated approach provides a validated and refined structural model of ligand–TAS2R14 interactions and a general framework for structure-based discovery in the absence of closely related experimental structures.
Effect of Substituent Size and Isomerization on the Polymorphism of 2-(Naphthalenylamino)-benzoic Acids
Liu, Yuting,Zhang, Mingtao,Xu, Danrui,Parkin, Sean,Li, Tonglei,Li, Conggang,Yang, Zhaoyong,Yu, Faquan,Long, Sihui
, p. 3694 - 3703 (2019/06/08)
To probe the effect of substituent size and isomerization on the polymorphism of fenamic acid (FA) derivatives, we synthesized two FA analogues, namely, 2-(naphthalen-1-ylamino)-benzoic acid and 2-(naphthalen-2-ylamino)-benzoic acid (NBAs), and investigat
Regioselective copper-catalysed amination of halobenzoic acids using aromatic amines
Maradolla, Mohan Babu,Mandha, Amaravathi,Garimella, Chandra Mouli
, p. 587 - 589 (2008/09/16)
Copper dipyridine dichloride (CuPy2Cl2) has been found to be an efficient catalyst for the synthesis of N-arylanthranilic acids from ortho halobenzoic acids and aromatic amines under microwave irradiation. Some of the advantages of this method are high chemoselectivity, ease of operation, less reaction times and high yields. (61-98%).
Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines
Wolf, Christian,Liu, Shuanglong,Mei, Xuefeng,August, Adam T.,Casimir, Michael D.
, p. 3270 - 3273 (2007/10/03)
A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).
