DBU-Mediated Efficient Synthesis of Indole-Conjugated Chromene Derivatives and Their Anticancer Evaluation and Molecular Modeling Study

A series of 9-(1 H -indol-3-yl)-2,3,4,9-tetrahydro-1 H -xanthen-1-one derivatives have been obtained by a one-pot three-component DBU-catalyzed reaction of 2-hydroxybenzaldehydes, cyclohexane-1,3-dione or 5,5-dimethylcyclohexane-1,3-dione , and 1 H -indoles in water under reflux for 60–90 min. This...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2023-05, Vol.59 (5), p.907-914
Main Authors: Ravi, Kurapati, Dhoddi, Bala Narsimha, Pochampally, Jalapathi
Format: Article
Language:English
Subjects:
Binding
Chemistry
Chemistry and Materials Science
Cyclohexane
Diketones
Hydroxybenzaldehydes
Indoles
Organic Chemistry
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Summary:A series of 9-(1 H -indol-3-yl)-2,3,4,9-tetrahydro-1 H -xanthen-1-one derivatives have been obtained by a one-pot three-component DBU-catalyzed reaction of 2-hydroxybenzaldehydes, cyclohexane-1,3-dione or 5,5-dimethylcyclohexane-1,3-dione , and 1 H -indoles in water under reflux for 60–90 min. This method offers remarkable advantages, including good yields of the target compounds, environmental safety, straightforward protocol, short reaction times, and mild reaction conditions. Most of the synthesized compounds showed good to moderate activity against PC-3 and SKOV-3 cancer cells. In silico binding studies revealed good binding affinities of 5-methoxy- and 5-methoxy-3,3-dimethyl-9-(1 H -indol-3-yl)-2,3,4,9-tetrahydro-1 H -xanthen-1-ones to human VEGFR-2 protein.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428023050214