97257-41-5Relevant academic research and scientific papers
Palladium-Catalyzed Three-Component Cascade Reaction of Nitriles: Synthesis of 2-Arylquinoline-4-carboxylates
Zhao, Zhiwei,Zeng, Ge,Chen, Yinan,Zheng, Jinming,Chen, Zhongyan,Shao, Yinlin,Zhang, Fangjun,Chen, Jiuxi,Li, Renhao
, p. 7955 - 7960 (2021/10/20)
A new method for converting easy availability starting materials 2-(2-oxoindolin-3-yl)acetonitrile, arylboronic acids, and alcohols into 2-arylquinoline-4-carboxylates is reported. The procedure involves a three-component addition/ring expansion/esterification reaction in the presence of Pd(II) catalyst with high functional group tolerance under mild conditions. In addition, the photophysical properties of the resulting product were investigated and exhibited excellent polarity-sensitive fluorescence properties and AIE property.
Design, Synthesis, and Biological Evaluation of 4-Quinoline Carboxylic Acids as Inhibitors of Dihydroorotate Dehydrogenase
Madak, Joseph T.,Cuthbertson, Christine R.,Miyata, Yoshinari,Tamura, Shuzo,Petrunak, Elyse M.,Stuckey, Jeanne A.,Han, Yanyan,He, Miao,Sun, Duxin,Showalter, Hollis D.,Neamati, Nouri
, p. 5162 - 5186 (2018/05/15)
We pursued a structure-guided approach toward the development of improved dihydroorotate dehydrogenase (DHODH) inhibitors with the goal of forming new interactions between DHODH and the brequinar class of inhibitors. Two potential residues, T63 and Y356, suitable for novel H-bonding interactions, were identified in the brequinar-binding pocket. Analogues were designed to maintain the essential pharmacophore and form new electrostatic interactions through strategically positioned H-bond accepting groups. This effort led to the discovery of potent quinoline-based analogues 41 (DHODH IC50 = 9.71 ± 1.4 nM) and 43 (DHODH IC50 = 26.2 ± 1.8 nM). A cocrystal structure between 43 and DHODH depicts a novel water mediated H-bond interaction with T63. Additional optimization led to the 1,7-naphthyridine 46 (DHODH IC50 = 28.3 ± 3.3 nM) that forms a novel H-bond with Y356. Importantly, compound 41 possesses significant oral bioavailability (F = 56%) and an elimination t1/2 = 2.78 h (PO dosing). In conclusion, the data supports further preclinical studies of our lead compounds toward selection of a candidate for early-stage clinical development.
Synthesis of 2-(4-biphenylyl)quinoline-4-carboxylate and carboxamide analogs. New human neurokinin-3 (hNK-3) receptor antagonists
Saudi, Manal N. S.,Rostom, Sherif A. F.,Fahmy, Hesham T. Y.,El Ashmawy, Ibrahim M.
, p. 165 - 174 (2007/10/03)
The 2-phenylquinoline-4-carboxamide 1 (Chart 1) has been found to possess moderate affinity for human neurokinin-3 (hNK-3) receptor. In the present work, and in a trial to investigate the effect of the lipophilic moiety at C-2 of the quinoline ring on the
