Synthesis of furo[3,2-]coumarin derivatives using visible-light-promoted radical alkyne insertion with bromocoumarins

The synthesis of privileged structures, which are potent drug candidates, is an impetus for drug discovery. The construction of heterocyclic framework furo[3,2- c ]coumarins using a visible-light promoted photoredox neutral coupling of 3-bromo-4-hydroxycoumarins with commercially available alkynes h...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-01, Vol.14 (25), p.665-67
Main Authors: Zhou, Hui, Deng, Xinzhao, Ma, Zhenjun, Zhang, Aihua, Qin, Qixue, Tan, Ren Xiang, Yu, Shouyun
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Chemistry Techniques, Synthetic
Coumarins - chemical synthesis
Coumarins - chemistry
Coumarins - pharmacology
Free Radicals - chemistry
Halogenation
HL-60 Cells
Humans
Light
Temperature
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Summary:The synthesis of privileged structures, which are potent drug candidates, is an impetus for drug discovery. The construction of heterocyclic framework furo[3,2- c ]coumarins using a visible-light promoted photoredox neutral coupling of 3-bromo-4-hydroxycoumarins with commercially available alkynes has been reported. These reactions can be carried out at room temperature under visible light irradiation with good chemical yields. This work presents 17 furocoumarins, 12 of which are new. Three of the newly synthesized compounds show potent cytotoxicity, and one shows moderate acetylcholinesterase inhibitory activity with IC 50 values of 2.16 ± 0.13 μM. Heterocyclic framework furo[3,2- c ]coumarins were constructed using a visible-light promoted photoredox neutral coupling of 3-bromo-4-hydroxycoumarins with commercially available alkynes.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob00768f