10.1007/s40097-017-0240-7

Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS

  1. Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, IR
  2. Department of Chemistry, RTM Nagpur University, Nagpur, 440033, IN
Cover Image

Published in Issue 20-09-2017

How to Cite

Maleki, A., Akbarzade, A. R., & Bhat, A. R. (2017). Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS. Journal of Nanostructure in Chemistry, 7(4 (December 2017). https://doi.org/10.1007/s40097-017-0240-7

PDF views: 137

HTML views: 35

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

  1. Weber (2002) The application of multicomponent reactions in drug discovery (pp. 2085-2093) https://doi.org/10.2174/0929867023368719
  2. 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
  3. Viswanadhan et al. (2002) Knowledge-based approaches in the design and selection of compound libraries for drug discovery (pp. 400-406)
  4. 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
  5. 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
  6. 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
  7. Wang and Astruc (2014) Fast-growing field of magnetically recyclable nanocatalysts (pp. 6949-6985) https://doi.org/10.1021/cr500134h
  8. 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
  9. 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
  10. 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
  11. Gati et al. (2012) De novo synthesis of 1,4-dihydropyridines and pyridines (pp. 9078-9081) https://doi.org/10.1021/ja303002a
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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