A simple, highly efficient, guanidine•HCl catalysed one-pot three-component synthesis of spiro chromeno-pyrimidin- and novel spiro pyrano-pyrimidin-indolinone derivatives and their anticancer activity against Burkitt's lymphoma CA-46 cell lines

A novel, efficient and guanidine•HCl catalysed synthesis of some important uracil and thiouracil-based spiro chromeno- and novel spiro pyrano-indolinones from cyclohexane/cyclopentane-1,3-diketones, malonyl ureas/thiourea and isatins/acenapthenequinone in water under thermal condition is reported. T...

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Bibliographic Details
Published inTetrahedron Vol. 158; p. 133980
Main Authors Khanum, Amreen, Afzal Pasha, Mohamed
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 30.05.2024
Subjects
Anticancer activity
Burkitt's lymphoma CA-46 cell lines
Cyclohexane/cyclopentane-1,3-diones
guanidine•HCl
Isatins/acenapthenequinone
Malonyl ureas/thiourea
MCF-7 and HeLa cell lines
Spiro chromeno-indolinones
Spiro pyrano-indolinones
Thermal condition
Water as a solvent
Cyclohexane/cyclopentane-1,3-diones
Burkitt's lymphoma CA-46 cell lines
Thermal condition
MCF-7 and HeLa cell lines
Spiro chromeno-indolinones
Anticancer activity
Spiro pyrano-indolinones
Malonyl ureas/thiourea
Isatins/acenapthenequinone
guanidine•HCl
Water as a solvent
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Summary:A novel, efficient and guanidine•HCl catalysed synthesis of some important uracil and thiouracil-based spiro chromeno- and novel spiro pyrano-indolinones from cyclohexane/cyclopentane-1,3-diketones, malonyl ureas/thiourea and isatins/acenapthenequinone in water under thermal condition is reported. The products are obtained in excellent yield within 40 min. Out of 36 test compounds, 21 were found to be very good inhibitors of Burkitt's Lymphoma CA-46 cell lines; and 2 of them are very powerful inhibitors. The 8 highly potent compounds which inhibited CA-46 cell lines did not show any activity towards MCF-7 and HeLa cell lines. [Display omitted] •Spiro chromeno-pyrimidin and novel spiro pyrano-pyrimidin-indolinones are synthesised.•Guanidine.•HCl is used as a green organocatalyst in water as a solvent.•The method is high yielding and versatile.•Anticancer activity against Burkitt's Lymphoma CA-46 cell lines has been studied.•The prepared molecules exhibit excellent anticancer activity and may be administered orally.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2024.133980