Generic placeholder image

Combinatorial Chemistry & High Throughput Screening

Editor-in-Chief

ISSN (Print): 1386-2073
ISSN (Online): 1875-5402

Research Article

Green Fabrication of Cobalt NPs using Aqueous Extract of Antioxidant Rich Zingiber and Their Catalytic Applications for the Synthesis of Pyrano[2,3-c]pyrazoles

Author(s): Robabeh Sabaghi Mianai, Mohammad Ali Ghasemzadeh* and Mohammad Reza Zand Monfared

Volume 22, Issue 1, 2019

Page: [18 - 26] Pages: 9

DOI: 10.2174/1386207322666190307160354

Price: $65

Abstract

Aim and Objective: In this study, biological synthesis of cobalt nanoparticles was developed in the presence of ginger extract as the reducing and capping agent through the simple and convenient co-precipitation method.

Materials and Methods: The as-synthesized cobalt nanoparticles were characterized by X-ray diffraction (XRD), scanning Electron Microscopy (SEM), spectra energy dispersive analysis of Xray (EDS), Fourier transform infrared (FT-IR), and vibrating sample magnetometer (VSM) techniques. According to the vibrating sample magnetometer, cobalt nanoparticles show paramagnetic behaviour at room temperature. Furthermore, the effect of ginger extract concentration on the UV-Vis absorbance of Co nanoparticles was investigated. Based on the UVVis absorbance spectra, increasing ginger extract concentration causes particle size to decrease. In addition, the catalytic performance of the synthesized cobalt nanoparticles was investigated in the preparation of pyrano[2,3-c]pyrazoles via one-pot four-component reactions of aryl aldehydes, hydrazine hydrate, malononitrile and diethyl acetylenedicarboxylate.

Result and Conclusion: The prepared pyrano[2,3-c]pyrazole derivatives were obtained in high yields within short reaction times and the nanocatalyst was easily separated using an external magnet and reused for several times with no significant loss of its activity.

Keywords: Cobalt, nanoparticles, bioreduction, extract, Zingiber, pyrano[2, 3-C]pyrazole.

[1]
Lu, A.H.; Salabas, E.L.; Schuth, F. Magnetic nanoparticles: Synthesis, protection, functionalization, and application. Angew. Chem. Int. Ed., 2007, 46, 1222-1244.
[2]
Khan, M.; Seubsai, A.; Onal, I.; Senkan, S. High throughput synthesis and screening of new catalytic materials for the direct epoxidation of propylene. Comb. Chem. High Throughput Screen., 2010, 13, 67-74.
[3]
Maleki, A.; Rabbani, M.; Shahrokh, S. Preparation and characterization of a silica‐based magnetic nanocomposite and its application as a recoverable catalyst for the one‐pot multicomponent synthesis of quinazolinone derivatives. Appl. Organomet. Chem., 2015, 29, 809-814.
[4]
Azizi, K.; Karimi, M.; Shaterianb, H.R.; Heydari, A. Ultrasound irradiation for the green synthesis of chromenes using L-arginine-functionalized magnetic nanoparticles as a recyclable organocatalyst. RSC Advances, 2014, 4, 42220-42225.
[5]
Mostafavi, M.M.; Movahedi, M. Fe3O4/MIL‐101(Fe) nanocomposite as an efficient and recyclable catalyst for Strecker reaction. Appl. Organometal. Chem., 2018.https://doi.org/ 10.1002/aoc.4217.
[6]
Zhu, L.P.; Zhang, W.D.; Xiao, H.M.; Yang, Y.; Fu, S.Y. Facile synthesis of metallic co hierarchical nanostructured microspheres by a simple solvothermal process. . J. Phys. Chem. C, 2008, 112, 10073-10078.
[7]
Matoussevitcha, N.; Gorschinskia, A.; Habichta, W.; Bolleb, J.; Dinjusa, E.; Bönnemanna, H.; Behrensa, S. Surface modification of metallic Co nanoparticles. . J. Magn. Magn. Mater., 2007, 311, 92-96.
[8]
Liu, W.; Zhong, W.; Wu, X.; Tang, N.; Du, Y. Hydrothermal microemulsion synthesis of cobalt nanorods and self-assembly into square-shaped nanostructures. . J. Cryst. Growth, 2005, 284, 446-452.
[9]
Su, Y.; Yang, X.; Tang, J. Spectra study and size control of cobalt nanoparticles passivated with oleic acid and triphenylphosphine. Appl. Surf. Sci., 2010, 256, 2353-2360.
[10]
Liang, X.; Zhao, L. Room-temperature synthesis of air-stable cobalt nanoparticles and their highly efficient adsorptionability for Congo red. RSC Advances, 2012, 2, 5485-5487.
[11]
Puntes, V.F.; Krishnan, K.M.; Alivisatos, A.P. Colloidal nanocrystal shape and size control: The case of cobalt. Science, 2001, 291, 2115-2117.
[12]
Skumryev, V.; Stoyanov, S.; Zhang, Y.; Hadjipanayis, G.; Givord, D.; Nogu’es, J. Beating the superparamagnetic limit with exchange bias. Nature, 2003, 423, 850-853.
[13]
Yu, Y.; Mendoza-Garcia, A.; Ning, B.; Sun, S. Cobalt‐substituted magnetite nanoparticles and their assembly into ferrimagnetic nanoparticle arrays. Adv. Mater., 2013, 25, 3090-3094.
[14]
Xiong, J.; Wang, Y.; Xue, Q.; Wu, X. Synthesis of highly stable dispersions of nanosized copper particles using L-ascorbic acid. Green Chem., 2011, 13, 900-904.
[15]
Raveendran, P.; Fu, J.; Wallen, S.L. Completely “green” synthesis and stabilization of metal nanoparticles. J. Am. Chem. Soc., 2003, 125, 13940-13941.
[16]
Liu, J.; Qin, G.; Raveendran, P.; Ikushima, Y. Facile “green” synthesis, characterization, and catalytic function of β‐D‐glucose‐stabilized Au nanocrystals. Chemistry Eur. J.,, 2006, 12, 2131-2138.
[17]
Abdel-Rahman, A.H.; Keshk, E.M.; Hanna, M.A.; El-Bady, S.M. Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents. Bioorg. Med. Chem., 2004, 12, 2483-2488.
[18]
Zaki, M.E.A.; Soliman, H.A.; Hiekal, O.A.; Rashad, A.E.Z. Pyrazolopyranopyrimidines as a class of anti-inflammatory agents. Z. Naturforsch., 2006, 61c, 1-5.
[19]
Wang, J.L.; Liu, D.; Zhang, Z.J.; Shan, S.; Han, X.; Srinivasula, S.M.; Huang, Z. Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc. Natl. Acad. Sci. USA, 2000, 97, 7124-7129.
[20]
Abdelrazek, F.M.; Metz, P.; Kataeva, O.; Jaeger, A.; El-Mahrouky, S.F. Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives. . Arch. Pharm. Chem. Life Sci, 2007, 340, 543-548.
[21]
Wu, H.; Zhang, L.L.; Tian, Z.Q.; Huang, Y.D.; Wang, Y.M. Highly efficient enantioselective construction of bispirooxindoles containing three stereocenters through an organocatalytic cascade michael–cyclization reaction. . Chemistry Eur. J., 2013, 19, 1747-1753.
[22]
Dandia, A.; Saini, D.; Bhaskaran, S.; Saini, D.K. Ultrasound promoted green synthesis of spiro[pyrano[2,3-c]pyrazoles] as antioxidant agents. Med. Chem. Res., 2014, 23, 725-734.
[23]
Mecadon, H.; Rohman, M.R.; Kharbangar, I.; Laloo, B.M.; Kharkongor, I.; Rajbangshi, M.; Myrboh, B. L-Proline as an efficicent catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitri-les in water. Tetrahedron Lett., 2011, 52, 3228-3231.
[24]
Liu, X.; Xu, X.; Wang, X.; Yang, W.; Qian, Q.; Zhang, M. A facile and convenient way to functionalized trifluoromethylated spirocyclic[indole-3,4-pyrano[2,3-c]pyrazole] derivatives. . Tetrahedron Lett., 2013, 54, 4451-4455.
[25]
Ambethkar, S.; Padmini, V.; Bhuvanesh, N. A green and efficient protocol for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives via a one-pot, four component reaction by grinding method. J. Adv. Res., 2015, 6, 975-985.
[26]
Rahath Kubra, I.; Ramalakshmi, K.; Mohan, Rao. L. Antioxidant enriched fractions from zingiber officinale roscoe. E-J. Chem., 2011, 8, 721-726.
[27]
Mukherjee, S.; Mandal, N.; Dey, A.; Mondal, B. An Approach towards optimization of the extraction of polyphenolic antioxidants from ginger (Zingiberofficinale). J. Food Sci. Technol., 2014, 51, 3301-3308.
[28]
Kumar, K.P.; Paul, W.; Sharma, C.P. green synthesis of silver Nanoparticles with Zingiberofficinale extract and study of its blood compatibility. BioNanoSci, 2012, 2, 144-152.
[29]
Rahmani, A.H. Al shabrmi, F.M.; Aly, S.M. Active ingredients of ginger as potential candidates in the prevention and treatment of diseases via modulation of biological activities. Int. J. Physiol. Pathophysiol. Pharmacol., 2014, 6, 125-136.
[30]
Prasad, S.; Tyagi, A.K. Ginger and its constituents: Role in prevention and treatment of gastrointestinal cancer. Gastroenterol. Res. Pract., 2015, 2015, 1-11.
[31]
Ghasemzadeh, M.A.; Elyasi, Z.; Azimi-Nasrabad, M.; Mirhosseini-Eshkevari, B. Magnetite nanoparticles-supported aptes as a powerful and recoverable nanocatalyst for the preparation of 2-amino-5,10-dihydro- 5,10-dioxo-4h-benzo[g]chromenes and tetr-ahydrobenzo[g]quinoline-5,10- diones. Comb. Chem. High Throughput Screen., 2017, 20, 64-76.
[32]
Ghasemzadeh, M.A.; Abdollahi-Basir, M.H.; Babaei, M. Fe3O4@SiO2-NH2 core-shell nancomposite as efficient and green catalyst for the multi-component synthesis of highly substituted chromeno[2,3-b]pyridines in aqueous ethanol media. . Green Chem. Lett. Rev., 2015, 8, 40-49.
[33]
Ghasemzadeh, M.A. Synthesis and characterization of Fe3O4@SiO2 NPs as an effective catalyst for the synthesis of tetrahydrobenzo[a]xanthen-11-ones. Acta Chim. Slov., 2015, 62, 977-985.
[34]
Hasan Nasrollahi, S.M.; Ghasemzadeh, M.A.; Zolfaghari, M.R. Synthesis and antibacterial evaluation of some new 1,4-dihydropyridines in the presence of Fe3O4@silica sulfonic acid nanocomposite as catalyst. Acta Chim. Slov., 2018, 65, 199-207.
[35]
Ansari, S.M.; Bhor, R.D.; Rai, K.R.; Sen, D.; Mazumde, S.; Ghosh, K.; Kolekar, Y.D.; Ramana, C.V. Cobalt nanoparticles for biomedical applications: Facile synthesis, physiochemical characterization, cytotoxicity behavior and biocompatibility. Appl. Surf. Sci., 2017, 414, 171-187.
[36]
Maddila, S.; Gorle, S.; Shabalala, S.; Oyetade, O.; Narayana, S.; Lavanya, P.; Jonnalagadda, S. Ultrasound mediated green synthesis of pyrano[2,3-c]pyrazoles by using Mndoped ZrO2. Arab. J. Chem., (in press).
[http://dx.doi.org/10.1016/j.arabjc.2016.04.016]
[37]
Azzam, S.H.S.; Pasha, M.A. Simple and efficient protocol for the synthesis of novel dihydro-1H-pyrano[2,3-c]pyrazol-6-ones via a one-pot four-componentreaction. Tetrahedron Lett., 2012, 53, 6834-6837.
[38]
Elnaghdi, N.M.H.; Al-Hokbany, N.S. Organocatalysis in synthesis: L-proline as an enantioselective catalyst in the synthesis of pyrans and Thiopyrans. Molecules, 2012, 17, 4300-4312.
[39]
Brahmachari, G.; Banerjee, B. Facile and one-pot access to diverse and densely functionalized 2-Amino-3-cyano -4H- pyrans and pyran – Annulated Heterocyclic Scaffolds via an eco-friendly multicomponent reaction at room temperature using urea as a novel organo-catalyst. ACS Sustain. Chem.& Eng., 2014, 2, 411-422.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy