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Current Organic Chemistry

Author(s): Dukanya, Toreshettahally R. Swaroop*, Kanchugarakoppal S. Rangappa and Basappa*

DOI: 10.2174/1385272824999201020204001

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Cyclocondensation of Sodium Azide with Methyl N(N),N'-di(tri)substituted Carbamimidothioate : A New Dimension for the Synthesis of 1,5-disubstituted Tetrazoles and Their Cytotoxicity against Human Breast Cancer Cells

Page: [2792 - 2799] Pages: 8

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Abstract

Synthesis of 1,5-disubstituted tetrazoles by the cyclization of sodium azide with N(N),N'-di(tri)substituted carbamimidothioate is reported. Tetrazoles are obtained in good to excellent yield in the absence of a catalyst. All the compounds were characterized by NMR and HRMS analysis. Single crystal X-ray diffraction data of 1-(4-chlorophenyl)-4-(5-phenyl- 1H-tetrazol-1-yl)piperazine 5g is also provided. Further, these disubstituted tetrazoles were tested against the proliferation of human breast cancer cells (MCF-7), which identified 5e as a lead compound. Finally, we have shown in silico that these compounds may interact with the ligand binding domain of estrogen receptor α (ERα), that expresses at high amount in MCF-7 cells.

Keywords: Cyclocondensation, carbamimidothioates, sodium azide, tetrazoles, cytotoxicity, MCF-7.

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