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DOI: 10.1055/a-2609-9848
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Yb(OTf)3-Catalyzed Synthesis of Thiochromeno[2,3-b]chromenes and Their Antiproliferative Study

Arnab Mandal
a   Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India
,
Satyajit Singh 
a   Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India
,
Sajib Daimary
a   Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India
,
Arisha Arora
b   Department of Bioscience and Bioengineering, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India
,
Sujisha S. Nambiar
b   Department of Bioscience and Bioengineering, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India
,
Siddhartha S. Ghosh
b   Department of Bioscience and Bioengineering, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India
,
Abu Taleb Khan  ∗
a   Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India
› Author Affiliations
A.M. thanks IIT Guwahati for providing an Institute Postdoctoral Fellowship through R&D (Project No. IITG/R&D/IPDF/2022-23/20220922P138). A.T.K. is grateful to the Department of Science and Technology, New Delhi, for financial support (Grant No. CRG/2022/002751/OC).
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Abstract

The synthesis of hitherto unreported thiochromeno[2,3-b]chromenes from 4-hydroxy-2H-chromene-2-thiones was investigated with salicylaldehydes and cyclohexane-1,3-diones in the presence of 10 mol% Yb(OTf)3 in toluene. The three-component reaction proceeds via Knoevenagel condensation between the cyclohexane-1,3-dione and the salicylaldehyde followed by Michael addition with the 4-hydroxy-2H-chromene-2-thione. The products were obtained in good to excellent yields, with retention of the sulfur atom in the heterocycle. This synthetic approach offers a straightforward and reliable method for preparing sulfur-containing heterocycles, potentially expanding the scope of thiochromene chemistry. A molecular docking study was performed on the synthesized derivatives, and two compounds demonstrated a dose-dependent antiproliferative effect and enhanced ROS generation in the MDA-MB-468 triple-negative breast cancer cell line.

Key words

4-hydroxy-2H-chromene-2-thiones - thiochromeno[2,3-b]chromenes - Yb(OTf)3 - linear products - cell viability - ROS detection

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2609-9848.
  • Supporting Information


Publication History

Received: 13 January 2025

Accepted: 14 May 2025

Accepted Manuscript online:
14 May 2025

Article published online:
12 June 2025

© 2025. Thieme. All rights reserved

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