Original scientific paper

https://doi.org/10.5562/cca4224

Synthesis, Characterization and Biological Evaluation of Imidazo[1,2-a]pyridine Integrated Thiazole Chalcones as Potent Anti-Breast Cancer and Antimicrobial Agents

Samadhan A. Shenmare ; Organic Chemistry Research Laboratory, School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapur University, Solapur-413255, Maharashtra, India
Dnyaneshwar M. Sirsat ; Department of Chemistry, Anandibai Raorane Arts, Commerce & Science College, Vaibhavwadi, Dist-Sindhudurg-416 810, Maharashtra, India
Sadanand N. Shringare ; Organic Chemistry Research Laboratory, School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapur University, Solapur-413255, Maharashtra, India
Nagesh V. Edake ; Organic Chemistry Research Laboratory, School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapur University, Solapur-413255, Maharashtra, India
Nikita N. Mali ; Department of Chemistry, Sub-Campus, Dr. Babasaheb Ambedkar Marathwada University, Dharashiv-413 501, Maharashtra, India
Raghunath B. Bhosale ; Organic Chemistry Research Laboratory, School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapur University, Solapur-413255, Maharashtra, India
Pravin S. Bhale orcid.org/0000-0003-3639-0357 ; Department of Chemistry, Yeshwantrao Chavan Mahavidyalaya, Tuljapur, Dist-Dharashiv-413601, Maharashtra, India *

* Corresponding author.

Supplements: cca4224_supplement.pdf

Abstract

A novel series of imidazo[1,2-a]pyridine–thiazole–chalcone hybrids (8a–l) were synthesized and evaluated for their in vitro anticancer and antimicrobial activities. The anticancer potential was assessed against the human breast cancer cell line MCF-7 using the sulforhodamine B (SRB) assay. Most of the synthesized compounds exhibited moderate cytotoxic activity, with compound 8i showing the highest potency (GI₅₀ = 19.0 µM) compared to the reference drug adriamycin (GI₅₀ = 0.4 µM). Structure–activity relationship (SAR) analysis revealed that electron-donating substituents, particularly methoxy groups at the para-position of the phenyl ring in the thiazole moiety, significantly enhanced anticancer activity, whereas electron-withdrawing groups such as cyano reduced it. The antimicrobial efficacy of the synthesized derivatives were determined by the disc diffusion method against bacteria. Several compounds, notably 8g, 8j, 8k, and 8l exhibited broad-spectrum antimicrobial activity comparable to the standard drug ciprofloxacin. Overall, these findings demonstrate that imidazo[1,2-a] pyridine–thiazole–chalcone hybrids represent a promising class of multifunctional bioactive molecules with significant anticancer and antimicrobial potential, offering valuable insights for future structural optimization and therapeutic development.

Keywords

imidazo[1,2-a] pyridine; thiazole; anti-cancer activity; antimicrobial activity

Hrčak ID:

343240

URI

https://hrcak.srce.hr/343240

Publication date:

31.12.2025.

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