Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS
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
Keywords
- Fe3O4/SiO2-OSO3H,
- Nanocatalyst,
- PASS program,
- Biological activity,
- Polyhydroquinolines
References
- Weber (2002) The application of multicomponent reactions in drug discovery (pp. 2085-2093) https://doi.org/10.2174/0929867023368719
- Maleki and Paydar (2015) Graphene oxide–chitosan bionanocomposite: a highly efficient nanocatalyst for the one-pot three-component synthesis of trisubstituted imidazoles under solvent-free conditions (pp. 33177-33184) https://doi.org/10.1039/C5RA03355A
- Viswanadhan et al. (2002) Knowledge-based approaches in the design and selection of compound libraries for drug discovery (pp. 400-406)
- Hulme et al. (2005) Applications of multicomponent reactions in drug discovery-lead generation to process development (pp. 311-341) Wiley-VCH Verlag GmbH & Co. KGaA https://doi.org/10.1002/3527605118.ch11
- Hulme et al. (2015) Recent advances in multicomponent reaction chemistry: applications in small molecule drug discovery (pp. 145-187) Weinheim https://doi.org/10.1002/9781118771723.ch6
- Zhang et al. (2012) Magnetically recyclable nanocatalysts (MRNCs): a versatile integration of high catalytic activity and facile recovery (pp. 6244-6255) https://doi.org/10.1039/c2nr31929b
- Wang and Astruc (2014) Fast-growing field of magnetically recyclable nanocatalysts (pp. 6949-6985) https://doi.org/10.1021/cr500134h
- Yang et al. (2013) Clean procedure for the synthesis of 1,4-dihydropyridines via Hantzsch reaction in water (pp. 262-267) https://doi.org/10.1080/17518253.2013.781686
- Mohamed et al. (2016) 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 (pp. 40900-40910) https://doi.org/10.1039/C6RA04974E
- Maiti et al. (2010) 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 (pp. 713-722) https://doi.org/10.1021/cc100084b
- Gati et al. (2012) De novo synthesis of 1,4-dihydropyridines and pyridines (pp. 9078-9081) https://doi.org/10.1021/ja303002a
- Sandjo et al. (2016) Synthesis and cytotoxicity of 1,4-dihydropyridines and an unexpected 1,3-oxazin-6-one (pp. 310-314) https://doi.org/10.1002/hlca.201500265
- Maleki et al. (2014) Synthesis and characterization of magnetic bromochromate hybrid nanomaterials with triphenylphosphine surface-modified iron oxide nanoparticles and their catalytic application in multicomponent reactions (pp. 29765-29771) https://doi.org/10.1039/C4RA04654D
- Lagunin et al. (2000) PASS: prediction of activity spectra for biologically active substances (pp. 747-748) https://doi.org/10.1093/bioinformatics/16.8.747
- Geronikaki et al. (2004) Design of new cognition enhancers: from computer prediction to synthesis and biological evaluation (pp. 2870-2876) https://doi.org/10.1021/jm031086k
- Maleki (2012) Fe3O4/SiO2 nanoparticles: an efficient and magnetically recoverable nanocatalyst for the one-pot multicomponent synthesis of diazepines (pp. 7827-7829) https://doi.org/10.1016/j.tet.2012.07.034
- Maleki (2013) One-pot multicomponent synthesis of diazepine derivatives using terminal alkynes in the presence of silica-supported superparamagnetic iron oxide nanoparticles (pp. 2055-2059) https://doi.org/10.1016/j.tetlet.2013.01.123
- Maleki (2014) 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 (pp. 64169-64173) https://doi.org/10.1039/C4RA10856F
- Maleki et al. (2015) Preparation and characterization of a new surface-modified dichromate/triethylamine/silica/iron oxide magnetic hybrid nanomaterial (pp. 191-196) https://doi.org/10.1007/s13738-014-0473-z
- Maleki et al. (2015) Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst (pp. 95-105) https://doi.org/10.1007/s40097-014-0140-z
- Maleki et al. (2014) Preparation and characterization of magnetic chlorochromate hybrid nanomaterials with triphenylphosphine surface-modified iron oxide nanoparticles (pp. 153-160) https://doi.org/10.1007/s40097-014-0131-0
- Maleki et al. (2017) Design and development of a novel magnetic camphor nanospheres core/shell nanostructure (pp. 149-157) https://doi.org/10.1007/s40097-017-0224-7
- Bhat et al. (2015) 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 (pp. 941-948) https://doi.org/10.1016/j.jare.2014.10.007
10.1007/s40097-017-0240-7