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.]
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.
Efficient synthesis of benzene-fused 6/7-membered amides: Via Xphos Pd G2 catalyzed intramolecular C-N bond formation
Xu, Zhou,Li, Ke,Zhai, Rongliang,Liang, Ting,Gui, Xiaodie,Zhang, Rongli
, p. 51972 - 51977 (2017/11/22)
An efficient approach for benzene-fused 6/7-membered amides via intramolecular amidation of aryl chlorides catalyzed by a Buchwald-Hartwig second generation Pd catalyst (Xphos Pd G2) has been successfully developed. This catalyst system allows the primary amides which have only modest nucleophilicity to be coupled successfully even with electron rich aryl chlorides in short reaction time. The intramolecular amidation reaction also has good chemoselectivity and excellent functional group compatibility.