HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives

doi:10.1002/chir.22969

CORC > 上海药物研究所 > 中国科学院上海药物研究所 > 药理学第二研究室

	HPLC-ECD and TDDFT-ECD study of hexahydropyrrolo[1,2-a]quinoline derivatives
	Toth, Laszlo 3,4; Mandi, Attila 4; Varadi, Daniel 4; Kovacs, Tibor 4; Szabados, Anna 4; Kiss-Szikszai, Attila 4; Gong, Qi 2; Zhang, Haiyan2 ; Matyus, Peter 1; Antus, Sandor 4
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.