Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel-[1,5]-hydride shift cyclization reaction
文献类型：期刊论文
| 作者 | Toth, Laszlo1,2; Fu, Yan3; Zhang, Hai Yan3; Mandi, Attila2; Kover, Katalin E.4; Illyes, Tunde-Zita2; Kiss-Szikszai, Attila2; Balogh, Balazs1; Kurtan, Tibor2,5; Antus, Sandor2 |
| 刊名 | BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2014-11-06 |
| 卷号 | 10页码:2594-2602 |
| 关键词 | 1,4-benzoxazepine diastereoselective domino Knoevenagel-[1,5]-hydride shift cyclization neuroprotective tert-amino effect TDDFT-ECD calculation |
| ISSN号 | 1860-5397 |
| DOI | 10.3762/bjoc.10.272 |
| 文献子类 | Article |
| 英文摘要 | Condensed O,N-heterocycles containing tetrahydro-1,4-benzoxazepine and tetrahydroquinoline moieties were prepared by a regio-and diastereoselective domino Knoevenagel-[1,5]-hydride shift cyclization reaction of a 4-aryl-2-phenyl-1,4-benzoxazepine derivative obtained from flavanone. The relative configuration of products were determined by the correlation of (3)J(H,H) coupling data with the geometry of major conformers accessed by DFT conformational analysis. Separated enantiomers of the products were characterized by HPLC-ECD data, which allowed their configurational assignment on the basis of TDDFT-ECD calculation of the solution conformers. Two compounds showed neuroprotective activities against hydrogen peroxide (H2O2) or beta-amyloid(25-35) (A beta(25-35))-induced cellular injuries in human neuroblastoma SH-SY5Y cells in the range of those of positive controls. |
| WOS关键词 | ASYMMETRIC-SYNTHESIS ; RING-SYSTEMS ; DERIVATIVES ; PICLOZOTAN ; ROCASTINE ; AGONISTS ; ANALOGS |
| 资助项目 | Hungarian National Research Foundation[OTKA K81701] ; European Union[00000000] ; European Social Fund through the project Supercomputer, the national virtual lab[TAMOP-4.2.2.C-11/1/KONV-2012-0010] ; [EAOP-1.1.3-12-2012-0026] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000344507300002 |
| 出版者 | BEILSTEIN-INSTITUT |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276843]  |
| 专题 | 药理学第二研究室 |
| 通讯作者 | Antus, Sandor |
| 作者单位 | 1.Semmelweis Univ, Dept Organ Chem, H-1092 Budapest, Hungary; 2.Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary; 3.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China; 4.Univ Debrecen, Dept Inorgan & Analyt Chem, H-4010 Debrecen, Hungary; 5.Porfirin Ltd, H-4032 Debrecen, Hungary |
| 推荐引用方式 GB/T 7714 | Toth, Laszlo,Fu, Yan,Zhang, Hai Yan,et al. Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel-[1,5]-hydride shift cyclization reaction[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,2014,10:2594-2602. |
| APA | Toth, Laszlo.,Fu, Yan.,Zhang, Hai Yan.,Mandi, Attila.,Kover, Katalin E..,...&Matyus, Peter.(2014).Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel-[1,5]-hydride shift cyclization reaction.BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,10,2594-2602. |
| MLA | Toth, Laszlo,et al."Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel-[1,5]-hydride shift cyclization reaction".BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 10(2014):2594-2602. |
入库方式： OAI收割
来源：上海药物研究所
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