(2S)-2-(Fluoromethyl)piperidine hydrochloride (1:1)
CAS Number:
886216-73-5
Molecular Formula:
C6H13ClFN
Isatin-based spiro indolenine alkaloids from Isatis indigotica Fortune with anti-neuroinflammatory and acetylcholinesterase inhibitory effects
Literature Information
Publication Date
2023-11-21
DOI
10.1039/D3QO01769A
Impact Factor
5.281
Authors
Ming Bai, Yu-Fei Xi, Si-Hui Mi, Pei-Yuan Yang, Li-Li Lou, Tian-Ming Lv, Xin Zhang, Guo-Dong Yao, Bin Lin, Shao-Jiang Song
View Original
Abstract
Isatin-based spiro indolenine alkaloids are derived from mixed biosynthetic origins, and the C-2 and C-3 carbonyl groups of isatin could be spirocyclic, thus achieving a variable chemical diversity. Four novel alkaloids (1a/1b, 2, and 3), featuring an unusual isatin-based spiro indolenine system, were obtained from the leaves of Isatis indigotica Fortune. Compounds 1a/1b were a pair of enantiomers characterized by an unprecedented 6/5/6/5/6 N,O-heterocyclic scaffold with a unique spiro[4.5] core. Compound 2 was the first 6/5/6/5/5/6 hexacyclic skeleton fused with an unexpected dispiro[4.4.0.4] system of an isatin-based alkaloid. Their structures were elucidated by 1D and 2D NMR and HRESIMS techniques as well as density functional theory (DFT) calculations and computer-assisted structure elucidation (CASE). The possible biosynthetic pathways for compounds 1a/1b–3 are proposed. In addition, all alkaloids were evaluated for their anti-neuroinflammatory and acetylcholinesterase inhibitory effects.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
1-(3,4-Dichlorophenyl)-1H-pyrazole-3-carboxylic acid
CAS Number:
1152949-12-6
Molecular Formula:
C10H6Cl2N2O2
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