7652-29-1Relevant articles and documents
Intramolecular cyclization of N-hydroxy-2-phenoxyacetamides and 3-phenoxypropanamides
Dittakavi, Ramachandran,Madhavarao, Nagarajan,Mannam, Krishnamurthy,Nagalingam, Viswanath,Sreenivasulu, Reddymasu
, (2020/08/06)
Abstract: A novel route for the preparation of 2H-1,4- benzoxazin-3(4H)one and 1,5 benzoxazepinones by intramolecular cyclization of N-hydroxy 2-phenoxyacetamide and N-hydroxy -3 phenoxypropanamide using PPA and Lewis acid has been discussed. Graphical abstract: [Figure not available: see fulltext. Caption: Preparation of 2H-1,4- benzoxazin-3(4H)one and 1,5 benzoxazepinones by electrophilic aromatic substitution from N-hydroxy 2-phenoxyacetamide and N-hydroxy -3 phenoxypropanamide and their acetyl and benzoyl derivatives using PPA and Lewis acids.]
Synthesis and biological evaluation of potential acetylcholinesterase inhibitors based on a benzoxazine core
Méndez-Rojas, Claudio,Quiroz, Gabriel,Faúndez, Mario,Gallardo-Garrido, Carlos,Pessoa-Mahana, C. David,Chung, Hery,Gallardo-Toledo, Eduardo,Saitz-Barría, Claudio,Araya-Maturana, Ramiro,Kogan, Marcelo J.,Zú?iga-López, María C.,Iturriaga-Vásquez, Patricio,Valenzuela-Gutiérrez, Carla,Pessoa-Mahana, Hernán
, (2018/04/06)
With the purpose of expanding the structural variety of chemical compounds available as pharmacological tools for the treatment of Alzheimer's disease, we synthesized and evaluated a novel series of indole-benzoxazinones (Family I) and benzoxazine-arylpiperazine derivatives (Family II) for potential human acetylcholinesterase (hAChE) inhibitory properties. The most active compounds 7a and 7d demonstrated effective inhibitory profiles with Ki values of 20.3 ± 0.9 μM and 20.2 ± 0.9 μM, respectively. Kinetic inhibition assays showed non-competitive inhibition of AChE by the tested compounds. According to our docking studies, the most active compounds from both series (Families I and II) showed a binding mode similar to donepezil and interact with the same residues.
Using gene expression database to uncover biology functions of 1,4-disubstituted 1,2,3-triazole analogues synthesized via a copper (I)-catalyzed reaction
Su, Chun-Li,Tseng, Chia-Ling,Ramesh, Chintakunta,Liu, Hsiao-Sheng,Huang, Chi-Ying F.,Yao, Ching-Fa
, p. 90 - 107 (2017/03/27)
We have synthesized bioactive 1,4-disubstituted 1,2,3-triazole analogues containing 2H-1,4-benzoxazin-3-(4H)-one derivatives via 1,3-dipolar cycloaddition in the presence of CuI. All the reactions proceeded smoothly and afforded its desired products in excellent yields. Among these analogues, 3y exhibited a better cytotoxic effect on human hepatocellular carcinoma (HCC) Hep 3B cells and displayed less cytotoxicity on normal human umbilical vein endothelial cells, compared with Sorafenib, a targeted therapy for advanced HCC. 3y also induced stronger apoptosis and autophagy. Addition of curcumin enhanced 3y-induced cytotoxicity by further induction of autophagy. Using gene expression signatures of 3y to query Connectivity Map, a glycogen synthase kinase-3 inhibitor (AR-A014418) was predicted to display similar molecular action of 3y. Experiments further demonstrate that AR-A014418 acted like 3y, and vice versa. Overall, our data suggest the chemotherapeutic potential of 3y on HCC.