Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS
Source abstract
Abstract
In this work, a library of diverse chemically and medicinally important heterocyclic polyhydroquinoline derivatives was efficiently prepared via a one-pot multicomponent reaction starting from various raw materials including aromatic aldehydes, dimedone or 1,3-cyclohexandione, ethyl acetoacetate or methyl acetoacetate and ammonium acetate in the presence of Fe 3 O 4 /SiO 2 -OSO 3 H as a sulfonated silica-based magnetic nanocatalyst in high yields. Main advantages of the present practical approach are ready availability of starting materials, non-toxicity, inexpensiveness, ease of workup procedure, diversity orientation synthesis and an eco-friendly nature of the reaction. The nanocatalyst was characterized by Fourier transform infrared (FT-IR) spectra, scanning electron microscopy (SEM) images and energy-dispersive X-ray spectroscopy (EDX) spectra. The nanocatalyst was simply recovered using an external magnet and reused several times. Then, the pharmacological and biological activities of the products were theoretically examined by the prediction of activity spectra for substances (PASS) program. Graphical abstract
Source: openalex_inverted_index · Quality: baseline
Research context
OpenAlex topics: Multicomponent Synthesis of Heterocycles · Synthesis and biological activity · Synthesis and Characterization of Heterocyclic Compounds
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (23)
Show source-provided references
1. Weber, L.: The application of multicomponent reactions in drug discovery. Curr. Med. Chem. 9, 2085–2093 (2002)10.2174/0929867023368719 ↗
2. Maleki, A., Paydar, R.: Graphene oxide–chitosan bionanocomposite: a highly efficient nanocatalyst for the one-pot three-component synthesis of trisubstituted imidazoles under solvent-free conditions. RSC Adv. 5, 33177–33184 (2015)10.1039/C5RA03355A ↗
3. Viswanadhan, V.N., Balan, C., Hulme, C., Cheetham, J.C., Sun, Y.: Knowledge-based approaches in the design and selection of compound libraries for drug discovery. Curr. Opin. Drug Disc. Devel. 5, 400–406 (2002)
4. Hulme, C.: Applications of multicomponent reactions in drug discovery-lead generation to process development. In: Zhu, J., Bienaymé, H. (eds.) Multicomponent Reactions, pp. 311–341. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim (2005)10.1002/3527605118.ch11 ↗
5. Hulme, C., Ayaz, M., Martinez-Ariza, G., Medda, F., Shaw, A.: Recent advances in multicomponent reaction chemistry: applications in small molecule drug discovery. In: Czechtizky, W., Hamley, P. (eds.) Small Molecule Medicinal Chemistry: Strategies and Technologies, 6th edn, pp. 145–187. Weinheim, Wiley (2015)10.1002/9781118771723.ch6 ↗
6. Zhang, D., Zhou, C., Sun, Z., Wu, L.-Z., Tung, C.-H., Zhang, T.: Magnetically recyclable nanocatalysts (MRNCs): a versatile integration of high catalytic activity and facile recovery. Nanoscale 4, 6244–6255 (2012)10.1039/c2nr31929b ↗
7. Wang, D., Astruc, D.: Fast-growing field of magnetically recyclable nanocatalysts. Chem. Rev. 114, 6949–6985 (2014)10.1021/cr500134h ↗
8. Yang, J., Jiang, C., Yang, J., Qian, C., Fang, D.A.: Clean procedure for the synthesis of 1,4-dihydropyridines via Hantzsch reaction in water. Green Chem. Lett. Rev. 6, 262–267 (2013)10.1080/17518253.2013.781686 ↗
9. Mohamed, M.F., Darweesh, A.F., Elwahy, A.H.M., Abdelhamid, I.A.: Synthesis, characterization and antitumor activity of novel tetrapodal 1,4-dihydropyridines: p53 induction, cell cycle arrest and low damage effect on normal cells induced by genotoxic factor H2O2. RSC Adv. 6, 40900–40910 (2016)10.1039/C6RA04974E ↗
10. Maiti, S., Sridharan, V., Menéndez, J.C.: Synthesis of a library of 5,6-unsubstituted 1,4-dihydropyridines based on a one-pot 4CR/elimination process and their application to the generation of structurally diverse fused nitrogen heterocycles. J. Comb. Chem. 12, 713–722 (2010)10.1021/cc100084b ↗
11. Gati, W., Rammah, M.M., Rammah, M.B., Couty, F., Evano, G.: De novo synthesis of 1,4-dihydropyridines and pyridines. J. Am. Chem. Soc. 134, 9078–9081 (2012)10.1021/ja303002a ↗
12. Sandjo, L.P., Kuete, V., Nana, F., Kirsch, G., Efferth, T.: Synthesis and cytotoxicity of 1,4-dihydropyridines and an unexpected 1,3-oxazin-6-one. Helv. Chim. Acta 99, 310–314 (2016)10.1002/hlca.201500265 ↗
13. Maleki, A., Rahimi, R., Maleki, S., Hamidi, N.: Synthesis and characterization of magnetic bromochromate hybrid nanomaterials with triphenylphosphine surface-modified iron oxide nanoparticles and their catalytic application in multicomponent reactions. RSC Adv. 4, 29765–29771 (2014)10.1039/C4RA04654D ↗
14. Lagunin, A., Stepanchikova, A., Filimonov, D., Poroikov, V.: PASS: prediction of activity spectra for biologically active substances. Bioinform. Appl. Note 16, 747–748 (2000)10.1093/bioinformatics/16.8.747 ↗
15. Geronikaki, A.A., Dearden, J.C., Filimonov, D., Galaeva, I., Garibova, L., Gloriozova, T., Kranjneva, V., Lagunin, A., Macaev, F.Z., Molodavkin, G., Poroikov, V., Pobrebnoi, S.I., Shepeli, F., Voronina, T., Tsitlakido, M., Vald, L.: Design of new cognition enhancers: from computer prediction to synthesis and biological evaluation. J. Med. Chem. 47, 2870–2876 (2004)10.1021/jm031086k ↗
16. Maleki, A.: Fe3O4/SiO2 nanoparticles: an efficient and magnetically recoverable nanocatalyst for the one-pot multicomponent synthesis of diazepines. Tetrahedron 68, 7827–7829 (2012)10.1016/j.tet.2012.07.034 ↗
17. Maleki, A.: One-pot multicomponent synthesis of diazepine derivatives using terminal alkynes in the presence of silica-supported superparamagnetic iron oxide nanoparticles. Tetrahedron Lett. 54, 2055–2059 (2013)10.1016/j.tetlet.2013.01.123 ↗
18. Maleki, A.: One-pot three-component synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolines using Fe3O4@SiO2-OSO3H as an efficient heterogeneous nanocatalyst. RSC Adv. 4, 64169–64173 (2014)10.1039/C4RA10856F ↗
19. Maleki, A., Rahimi, R., Maleki, S.: Preparation and characterization of a new surface-modified dichromate/triethylamine/silica/iron oxide magnetic hybrid nanomaterial. J. Iran. Chem. Soc. 12, 191–196 (2015)10.1007/s13738-014-0473-z ↗
20. Maleki, A., Kamalzare, M., Aghaei, M.: Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst. J. Nanostruct. Chem. 5, 95–105 (2015)10.1007/s40097-014-0140-z ↗
21. Maleki, A., Rahimi, R., Maleki, S.: Preparation and characterization of magnetic chlorochromate hybrid nanomaterials with triphenylphosphine surface-modified iron oxide nanoparticles. J. Nanostruct. Chem. 4, 153–160 (2014)10.1007/s40097-014-0131-0 ↗
22. Maleki, A., Zand, P., Mohseni, Z.: Design and development of a novel magnetic camphor nanospheres core/shell nanostructure. J. Nanostruct. Chem. 7, 149–157 (2017)10.1007/s40097-017-0224-7 ↗
23. Bhat, A.R., Shalla, A.H., Dongre, R.S.: Microwave assisted one-pot catalyst-free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity. J. Adv. Res. 6, 941–948 (2015)10.1016/j.jare.2014.10.007 ↗