Synthesis and Biological Evaluation of Some Coumarin–Triazole Conjugates as Potential Anticancer Agents
Despite the discovery of many chemotherapeutic drugs that prevent uncontrolled cell division processes, the development of compounds with higher anticancer efficacy and a lower level of side effects is an important task in modern pharmaceutical chemistry. Herein, a mild and convenient method for the...
Saved in:
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-03-01
|
| Series: | Scientia Pharmaceutica |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2218-0532/93/2/16 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Summary: | Despite the discovery of many chemotherapeutic drugs that prevent uncontrolled cell division processes, the development of compounds with higher anticancer efficacy and a lower level of side effects is an important task in modern pharmaceutical chemistry. Herein, a mild and convenient method for the preparation of N1-substituted 3-(1,2,3-triazolyl-methoxycarbonyl)coumarins or <i>bis</i>(coumarine-3-carboxylate)<i>bis</i>(triazole)alkandiyl by the copper(I)-catalyzed Huisgen cycloaddition reaction of readily available coumarin-3-carboxylic acid propynyl ester with azides or diazides has been presented. The synthesized compounds have been tested for their cytotoxicity on various cancer and noncancerous cell lines using the MTT assay. All new compounds were nontoxic on normal epithelial VERO cells. Two derivatives exhibited selectivity towards HPV-negative human cervical cancer cells, C33 A, with excellent activities in low concentrations (GI<sub>50</sub> 4.4–7.0 µM). In vitro mechanistic studies showed that bis(coumarine)bis(triazolylester) conjugate <b>3</b> induced time-dependent apoptosis in cervical cancer cell lines C33 A and CaSki, at the GI<sub>50</sub> concentration, as measured by Annexin V-FITC/PI staining. The most active coumarin–triazolyl ester conjugate <b>2g</b> possessed anticancer activities, as indicated by its ability to induce S/G2 phase cell cycle arrest at a low concentration and early apoptosis in CaSki cells. The obtained results revealed the potential of new compounds as anticancer agents, particularly against cervical cancer. |
|---|---|
| ISSN: | 0036-8709 2218-0532 |