Iranian journal of Pediatric Hematology and Oncology

en 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 عمومى General پژوهشي Research <div style="text-align: justify;">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. </div> 3-Aminopyridine, Cancer, Doxorubicin, Graphene oxide 812 825 http://ijpho.ssu.ac.ir/browse.php?a_code=A-10-488-2&slc_lang=en&sid=1 Hamideh Emtiazi Hamideh Emtiazi hamideh.emtiazi@yahoo.com 0000-0001-7883-5145 Yes Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran Leila Amiri‑Zirtol Leila Amiri‑Zirtol L.amiri@rocketmail.com 0000-0002-6845-4872 No Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran Hadi Zare Zardini Hadi Zare Zardini hadizarezardini@gmail.com 0000-0002-1501-2560 No Hematology and Oncology Research Center, Noncommunicable Diseases Research Institute, Shahid Sadoughi University of Medical Sciences, Yazd, Iran Hematology and Oncology Research Center, Noncommunicable Diseases Research Institute, Shahid Sadoughi University of Medical Sciences, Yazd, Iran Amir Abbas Mohammadi Hamaneh Amir Abbas Mohammadi Hamaneh A.mohammadi0800@gmail.com 0009-0002-2497-8458 No Department of pharmacology, School of medicine, Tehran University of Medical Sciences, Tehran, Iran Department of pharmacology, School of medicine, Tehran University of Medical Sciences, Tehran, Iran Soghra Khabnadideh Soghra Khabnadideh Khabns@gmail.com 0000-0003-1176-6143 No Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran Bebe Zahra Modaresi Bebe Zahra Modaresi Zahra.modaresy@ut.ac.ir 0009-0000-2497-8458 No Chemical Engineering (Biotecnology), Faculty of Engineering, University of Tehran, Iran Chemical Engineering (Biotecnology), Faculty of Engineering, University of Tehran, Iran