HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives | |
Toth, Laszlo3,4; Mandi, Attila4; Varadi, Daniel4; Kovacs, Tibor4; Szabados, Anna4; Kiss-Szikszai, Attila4; Gong, Qi2; Zhang, Haiyan2; Matyus, Peter1; Antus, Sandor4 | |
刊名 | CHIRALITY |
2018-07 | |
卷号 | 30期号:7页码:866-874 |
关键词 | [1,5]-hydride shift C-H activation density functional theory relative and absolute configuration |
ISSN号 | 0899-0042 |
DOI | 10.1002/chir.22969 |
文献子类 | Article |
英文摘要 | Synthesis of racemic hexahydropyrrolo[1,2-a]quinoline derivatives (1-8) was performed by utilizing the Knoevenagel-[1,5]-hydride shift-cyclization domino reaction. Separation of the enantiomers of the chiral products (1-8) was carried out by chiral high-performance liquid chromatography, and online high-performance liquid chromatography-electronic circular dichroism (ECD) spectra were recorded to elucidate the absolute configuration by comparing the experimental and time-dependent density functional theory-ECD spectra obtained at various theoretical levels. For 1 of the products, the time-dependent density functional theory-ECD calculations allowed determining both the relative and the absolute configuration by distinguishing the 4 stereoisomers. One of the compounds with spiro 1,3-cyclohexanedione moiety (7) possessed moderate acetylcholinesterase inhibitory activity, while 3 showed neuroprotective activity in oxygen-glucose deprivation-induced neurotoxicity in human neuroblastoma SH-SY5Y cells. |
资助项目 | National Research, Development and Innovation Office[NKFI K120181] ; National Research, Development and Innovation Office[K112951] ; National Research, Development and Innovation Office[PD121020] ; National Research, Development and Innovation Office[TAMOP 4.2.4. A/2-11-1-2012-0001] ; Governmental Information-Technology Development Agency (KIFU)[00000000] |
WOS关键词 | SCOPE |
WOS研究方向 | Pharmacology & Pharmacy ; Chemistry |
语种 | 英语 |
出版者 | WILEY |
WOS记录号 | WOS:000435080300003 |
内容类型 | 期刊论文 |
源URL | [http://119.78.100.183/handle/2S10ELR8/279688] |
专题 | 药理学第二研究室 |
通讯作者 | Mandi, Attila; Kurtan, Tibor |
作者单位 | 1.Semmelweis Univ, Inst Digital Hlth Sci, Budapest, Hungary 2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai, Peoples R China; 3.Semmelweis Univ, Dept Organ Chem, Budapest, Hungary; 4.Univ Debrecen, Dept Organ Chem, POB 400, H-4002 Debrecen, Hungary; |
推荐引用方式 GB/T 7714 | Toth, Laszlo,Mandi, Attila,Varadi, Daniel,et al. HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives[J]. CHIRALITY,2018,30(7):866-874. |
APA | Toth, Laszlo.,Mandi, Attila.,Varadi, Daniel.,Kovacs, Tibor.,Szabados, Anna.,...&Kurtan, Tibor.(2018).HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives.CHIRALITY,30(7),866-874. |
MLA | Toth, Laszlo,et al."HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives".CHIRALITY 30.7(2018):866-874. |
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