39522-26-4Relevant 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.]
Synthetic technology for preparing 1,4-benzoxazinone through microwave process
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Paragraph 0022; 0023; 0024; 0031; 0032; 0033-0048, (2018/01/12)
The invention relates to a preparation method for a benzoxazine compound. The method comprises the following steps: adding the compound shown as formula II, methyl alcohol and catalyst into a reactor; reacting under the existence of catalyst and alkali; and performing post-processing after ending the reaction, thereby acquiring the compound shown as formula I. In the formula, R group is selected from hydrogen, amino, nitro, C1-C6 alkyl, C1-C6 alkoxy and hydroxy; alkyl is selected from methyl, ethyl and isopropyl; alkoxy is selected from methoxy group, ethyoxyl and isopropoxy. The method is low in cost of raw materials, is safe and reliable, is completed under normal temperature and normal pressure and is simple in process.
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.