Synthesis and Anticancer Activity of New Pyridine-Thiophene and Pyridine-Furan Hybrid Compounds, Their Sugar Hydrazone,
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ynthesis and Anticancer Activity of New Pyridine-Thiophene and Pyridine-Furan Hybrid Compounds, Their Sugar Hydrazone, and Glycosyl Derivatives H. S. Khalafa,b, H. E. M. Tolana, M. N. El-Bayaaa,*, M. A. A. Radwanc,d, M. El-Manawatye, and W. A. El-Sayeda,d,** a
b
Photochemistry Department, National Research Centre, Dokki, Giza, 12622 Egypt Chemistry Department, College of Science and Arts-Qurayat, Jouf University, Sakaka, 42421 Saudi Arabia c Applied Organic Chemistry Department, National Research Center, Dokki, Giza, 12622 Egypt d Department of Chemistry, Collage of Science, Qassim University, Buridah, 51452 Saudi Arabia e Pharmacognosy Department, National Research Centre, Dokki, Giza, 12622 Egypt e-mail: *[email protected]; **[email protected] Received June 26, 2020; revised July 30, 2020; accepted August 25, 2020
Abstract—New sugar hydrazones and their derived oxadiazolyl acyclic nucleoside analogs in addition to the derived thioglycosides incorporating pyridine, furan or thiophene have been synthesized via a multi-component reaction (MCR). The acetylated derivatives of hydrazones and the derived deprotected thioglycosides of the prepared acetylated analogs have been also synthesized. Anticancer activity of the products has been tested against adenocarcinomic human alveolar basal epithelial (A549), human prostatic adenocarcinoma (PC3) and human colorectal carcinoma (HCT116) cell lines in addition to their effect on human normal retinal pigmented epithelial cell line (RPE1) using the MTT assay. Three products: acid hydrazide, sugar hydrazine and glycoside are characterized by high activity against three cancer cell lines. Keywords: pyridine, thiophene, sugar, hydrazones, thioglycosides, anticancer
DOI: 10.1134/S1070363220090182 INTRODUCTION Pyridine derivatives demonstrate a broad spectrum of biological activities including antiviral [1, 2], anticancer [3, 4], antioxidant [5], and antimicrobial [6, 7]. Molecular structures of many alkaloids are based mainly on the pyridine system in addition to nicotinic acid known as vitamin B3 and niacin [8, 9]. Thiophenes are found in many natural products and incorporated in various synthetic compounds, demonstrating such biological activities as antimicrobial [10], antifungal [11] and anticancer [12, 13]. Thiophene derivatives possess cytotoxic activit against several cancer cell types, such as leukemia, ovarian, glioma, renal, and lung, induced cell cycle arrest and apoptosis and affected tubulin polymerization [14, 15]. Several furan-based products exhibited potent anticancer, antimicrobial and some more activities [16–18]. Moreover, tetrahydrofuryl moiety is the main molecular core of many important C-glycosides [19, 20] from the point of biological and chemical importance.
On the other hand, nucleosides analogs with improved base motif and/or sugar moiety revealed important medicinal properties such as antibiotic, antiviral and antitumor [21–23]. Consequently, and owing to our interest in the synthesis of potent sugar based heterocycles [24–27], the present stu
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