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Volume 16, Issue 2 (3-2026)
Iran J Ped Hematol Oncol 2026, 16(2): 812-825 |
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Ethics code: IR.SSU.MEDICINE.REC.1394.542
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Emtiazi H, Amiri‑Zirtol L, Khabnadideh S, Mohammadi Hamaneh A A, Khabnadideh S, Modaresi B Z. Synthesis of Dhydropyrano[3,2-c]chromenes in the Presence of Effective Acid–Base Nano Catalyst (3-Aminopyridin/Go) and Evaluation of Their Toxicity against Cancer Cells. Iran J Ped Hematol Oncol 2026; 16 (2) :812-825
URL: http://ijpho.ssu.ac.ir/article-1-938-en.html
URL: http://ijpho.ssu.ac.ir/article-1-938-en.html
Hamideh Emtiazi * 
, Leila Amiri‑Zirtol , Soghra Khabnadideh , Amir Abbas Mohammadi Hamaneh , Soghra Khabnadideh , Bebe Zahra Modaresi
, Leila Amiri‑Zirtol , Soghra Khabnadideh , Amir Abbas Mohammadi Hamaneh , Soghra Khabnadideh , Bebe Zahra Modaresi
Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran & Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
Abstract: (23 Views)
Background: Dihydropyrano[3,2-c]chromenes are oxygen-containing heterocycles with reported anticancer potential, yet green and efficient synthetic methods remain limited. Conventional catalysts often involve harsh conditions or low reusability. This study aimed to develop a sustainable, high-yield synthesis of chromenes via a novel acid–based nanocatalyst (GO/3-aminopyridine), and to evaluate the cytotoxicity of selected derivatives against cancer and normal cells.
Materials and Methods: In this in vitro experimental study, we performed a one-pot, three-component reaction of 4-hydroxycoumarin, malononitrile or ethyl cyanoacetate, and aromatic aldehydes in the presence of 3-aminopyridine-functionalized graphene oxide (GO/3-APy) under mild conditions (EtOH/H₂O, 50 °C). The structure of the catalyst and products were confirmed via FT‑IR, NMR, XRD, FE-SEM, and EDS. MTT assay was used to determine IC₅₀ values for selected compounds against Ovcar3, T47D, CA46, and HFF cell lines. Doxorubicin served as a positive control. Statistical analyses were done by SPSS (Version 22.0). ANOVA test was performed to identify significant differences in IC₅₀ values across all tested compounds and doxorubicin. P-value < 0.05 was considered significant.
Results: Compound 4b exhibited potent cytotoxicity against Ovcar3 (IC₅₀ = 14.67 ± 1.15 µg/mL), T47D (26.85 ± 2.10 µg/mL), and CA46 (27.17 ± 1.55 µg/mL) cells, significantly surpassing doxorubicin against CA46 (46.07 ± 2.80 µg/mL; p < 0.05). Compound 4d showed comparable activity (IC₅₀ = 17.99 ± 1.42, 29.50 ± 1.85, and 56.62 ± 2.90 µg/mL, respectively) with high selectivity for cancer cells over normal HFF (IC₅₀ = 239.25 ± 5.50 µg/mL; selectivity index ~13). Compounds 4e, 4g, and 4h demonstrated moderate cytotoxicity (IC₅₀ = 33.50–141.52 µg/mL), while doxorubicin displayed non-selective toxicity toward normal cells (IC₅₀ = 50.45 ± 2.90 µg/mL vs. 239.25 µg/mL for 4d).
Conclusion: The results of our research showed that dihydropyrano[3,2-c]chromene derivatives showed anticancer effects that depended on the type of substitution present on the ring in their structure.
Materials and Methods: In this in vitro experimental study, we performed a one-pot, three-component reaction of 4-hydroxycoumarin, malononitrile or ethyl cyanoacetate, and aromatic aldehydes in the presence of 3-aminopyridine-functionalized graphene oxide (GO/3-APy) under mild conditions (EtOH/H₂O, 50 °C). The structure of the catalyst and products were confirmed via FT‑IR, NMR, XRD, FE-SEM, and EDS. MTT assay was used to determine IC₅₀ values for selected compounds against Ovcar3, T47D, CA46, and HFF cell lines. Doxorubicin served as a positive control. Statistical analyses were done by SPSS (Version 22.0). ANOVA test was performed to identify significant differences in IC₅₀ values across all tested compounds and doxorubicin. P-value < 0.05 was considered significant.
Results: Compound 4b exhibited potent cytotoxicity against Ovcar3 (IC₅₀ = 14.67 ± 1.15 µg/mL), T47D (26.85 ± 2.10 µg/mL), and CA46 (27.17 ± 1.55 µg/mL) cells, significantly surpassing doxorubicin against CA46 (46.07 ± 2.80 µg/mL; p < 0.05). Compound 4d showed comparable activity (IC₅₀ = 17.99 ± 1.42, 29.50 ± 1.85, and 56.62 ± 2.90 µg/mL, respectively) with high selectivity for cancer cells over normal HFF (IC₅₀ = 239.25 ± 5.50 µg/mL; selectivity index ~13). Compounds 4e, 4g, and 4h demonstrated moderate cytotoxicity (IC₅₀ = 33.50–141.52 µg/mL), while doxorubicin displayed non-selective toxicity toward normal cells (IC₅₀ = 50.45 ± 2.90 µg/mL vs. 239.25 µg/mL for 4d).
Conclusion: The results of our research showed that dihydropyrano[3,2-c]chromene derivatives showed anticancer effects that depended on the type of substitution present on the ring in their structure.
Type of Study: Research |
Subject:
General
Received: 2025/02/19 | Accepted: 2026/03/28 | Published: 2026/03/28
Received: 2025/02/19 | Accepted: 2026/03/28 | Published: 2026/03/28
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