2nd International Conference on Chemo and Bioinformatics ICCBIKG 2023 (559-562)
АУТОР(И) / AUTHOR(S): Bojan D. Levovnik, Aleksa P. Alargić, Miloš M. Svirčev, Goran I. Benedeković
Е-АДРЕСА / E-MAIL: milos.svircev@dh.uns.ac.rs
DOI: 10.46793/ICCBI23.559L
САЖЕТАК / ABSTRACT:
Abstract: Styryl-lactones are a class of natural products and related analogs that exhibit diverse biological activities, including anticancer, anti-inflammatory, and antimicrobial properties. Since these compounds are routinely obtained in our laboratory from their O-isopropylidene precursors, we envisioned the project to examine and compare their respective structures and in-vitro activities. This paper presents a basic 3D-QSAR steric model built on a small set of 11 selected O-isopropylidene and styryl-lactone (particularly [3.3.0]furofuranone) ligands and their in vitro activities against an MCF-7 cell line. It is part of a larger ongoing study that encompasses synthesis as well as in vitro and in silico testing of a growing library of natural products and their analogs, with the aim to determine their pharmacophores, molecular targets, and cellular mechanisms of action.
КЉУЧНЕ РЕЧИ / KEYWORDS:
3D-QSAR, O-isopropylidene, styryl-lactone, ADME
ЛИТЕРАТУРА / REFERENCES:
T.F. Tam, B. Fraser-Reid., 1,2-O-isopropylidene furanoses as chiral precursors for α-methylene-γ-butyrolactones, J. Chem. Soc., Chem. Commun., (1980) 556–558.
K.M. Sun, B. Fraser-Reid, T.F. Tam., Annulated sugars: the 1,2-O-isopropylidene ring as a stereo-, regio-, and chemoselective agent, J. Am. Chem. Soc., 104 (1982) 367–369.
S.B. Ferreira, A.C.R. Sodero, M.F.C. Cardoso, E.S. Lima, C.R. Kaiser, F.P. Silva, V.F.
Ferreira., Synthesis, Biological Activity, and Molecular Modeling Studies of 1 H -1,2,3-Triazole Derivatives of Carbohydrates as α-Glucosidases Inhibitors, J. Med. Chem., 53 (2010) 2364–2375.M. Korycka-Machała, A. Brzostek, B. Dziadek, M. Kawka, T. Popławski, Z. Witczak, J. Dziadek., Evaluation of the Mycobactericidal Effect of Thio-functionalized Carbohydrate Derivatives, Molecules, 22 (2017) 812.
G. Catelani, F. Osti, N. Bianchi, M.C. Bergonzi, F. D’Andrea, R. Gambari., Induction of erythroid differentiation of human K562 cells by 3-O-acyl-1,2-O-isopropylidene-D-glucofuranose derivatives, Bioorg. Med. Chem. Lett., 9 (1999) 3153–3158.
J. Xing, J. Sun, H. You, J. Lv, J. Sun, Y. Dong., Anti-Inflammatory Effect of 3,4-Oxo-isopropylidene-shikimic Acid on Acetic Acid-Induced Colitis in Rats, Inflammation, 35 (2012) 1872–1879.
R.A. Aitken, L.A. Power., 1,3-Dioxoles and 1,3-Oxathioles, in: Compr. Heterocycl. Chem. III, Elsevier, 2008: pp. 841–891.
M. Svirčev, G. Benedeković, I. Kovačević, M. Popsavin, V. Kojić, D. Jakimov, T. Srdić-Rajić, M. V. Rodić, V. Popsavin., Conformationally restricted goniofufurone mimics with halogen, azido or benzoyloxy groups at the C-7 position: Design, synthesis and antiproliferative activity, Tetrahedron,
74 (2018) 4761–4768.B.D. Levovnik, J.D. Kesić, S.M. Đokić, M.M. Svirčev, A variation in the initial step in the synthesis of halogenated goniofufurone/tiazofurin analogs and in silico search for their receptors, in: 8th Conf. Young Chem. Serbia, Serbian Chemical Society, Serbian Young Chemists’ Club, Belgrade, 2019: p. 105.
R. Ragno., www3d-qsar.com: a web portal that brings 3-D QSAR to all electronic devices—the Py-CoMFA web application as tool to build models from pre-aligned datasets, J. Comput. Aided. Mol. Des., 33 (2019) 855–864.