Generic placeholder image

Current Chemical Biology

Editor-in-Chief

ISSN (Print): 2212-7968
ISSN (Online): 1872-3136

Research Article

Synthesis and Characterization of Selenium Containing Schiff Bases: The Selenosemicarbazones

Author(s): Anuraj S. Kshirsagar and Pawan Kumar Khanna*

Volume 16, Issue 1, 2022

Published on: 01 April, 2022

Page: [25 - 34] Pages: 10

DOI: 10.2174/2212796816666220223145742

Price: $65

Abstract

Background: Many organoselenium compounds are well known for their applications in various fields. However, some of the organoselenium compounds, like selenosemicarbazones, due to difficulties in their synthesis are not much explored. Herein, we present the synthesis and characterization of five different new selenosemicarbazones.

Objective: The study aimed to carry out the synthesis and characterization of novel selenosemicarbazones, a type of Schiff bases.

Methods: Selenosemicarbazones are synthesized in a single step, i.e., acid-catalyzed condensation reaction between ketones and hydrazine hydrate in the presence of potassium selenocyanate (KSeCN).

Results: Butyrophenone, 4-phenyl 2-butanone, 2-acetonaphthone, 4-nitroacetophenone and menthone were reacted with in-situ generated selenosemicarbazide, which led to the formation of respective selenosemicarbazones. These organoselenium derivatives of Schiff bases have been characterized by mass spectrometry, proton, carbon and selenium NMR.

Conclusion: The yields of synthesized butyrophenone, 4-phenyl 2-butanone, 2-acetonaphthone, 4- nitroacetophenone, and menthone selenosemicarbazones varied in between 44 to 65%. The synthesis strategy involved one-pot synthesis of selenosemicarbazone without isolation of toxic selenosemicarbazide.

Keywords: Selenosemicarbazide, selenosemicarbazone, condensation, Schiff base, organometallics, selenium.

Graphical Abstract

[1]
Jain, V.K. Organoselenium Compounds in Biology and Medicine: Synthesis, Biological and Therapeutic Treatments; RSC, 2018, pp. 1-33.
[http://dx.doi.org/10.1039/9781788011907]
[2]
(a) Braga, A.L.; Lüdtke, D.S.; Vargas, F.; Braga, R.C. Catalytic applications of chiral organoselenium compounds in asymmetric synthesis. Synlett, 2006, 10(10), 1453-1466.
[http://dx.doi.org/10.1055/s-2006-941592]
(b) Santi, C.; Santoro, S.; Battistelli, B. Organoselenium compounds as catalysts in nature and laboratory. Curr. Org. Chem., 2010, 14(20), 2442-2462.
[http://dx.doi.org/10.2174/138527210793358231]
[3]
Stanley, W.; VanDeMark, M.R.; Kumler, P.L. J. Chem. Soc. Photochemistry of organoselenium compounds. J. Chem. Soc. Chem. Commun., 1974, 17, 700-701.
[http://dx.doi.org/10.1039/c39740000700]
[4]
Narajji, C.; Karvekar, M.D.; Das, A.K. Biological importance of organoselenium compounds. Indian J. Pharm. Sci., 2007, 69(3), 344-351.
[http://dx.doi.org/10.4103/0250-474X.34541]
[5]
Molter, A.; Mohr, F. Indium(III), antimony(III) and bismuth(III) dihalide complexes with tridentate, anionic thio- and selenosemicarbazonato ligands. Dalton Trans., 2011, 40(14), 3754-3758.
[http://dx.doi.org/10.1039/c0dt01693d] [PMID: 21380464]
[6]
Patra, A.; Bendikov, M. Selenium- and tellurium-containing organic Π-conjugated oligomers and polymers.Organic Selenium and Tellurium Compounds; 3ed; 523. John Wiley & Sons: Chichester, England, 2012.
[7]
(a) Kshirsagar, A.S.; More, P.V.; Khanna, P.K. Synthesis of shape and size-controlled copper indium diselenide (CuInSe2) via extrusion of selenium from 1,2,3-selenadiazole. RSC Advances, 2016, 6(89), 86137-86150.
[http://dx.doi.org/10.1039/C6RA16933C]
(b) Kshirsagar, A.S.; Khanna, P.K. Reaction tailoring for synthesis of phase-pure nanocrystals of AgInSe2, Cu3SbSe3 and CuSbSe2. ChemistrySelect, 2018, 3(10), 2854-2866.
[http://dx.doi.org/10.1002/slct.201702986]
[8]
Paterson, B.M.; Donnelly, P.S. Copper complexes of bis(thiosemicarbazones): From chemotherapeutics to diagnostic and therapeutic radiopharmaceuticals. Chem. Soc. Rev., 2011, 40(5), 3005-3018.
[http://dx.doi.org/10.1039/c0cs00215a] [PMID: 21409228]
[9]
(a) Garg, B.S.; Jain, V.K. Analytical applications of thiosemicarbazones and semicarbazones. Microchem. J., 1988, 38(2), 144-169.
[http://dx.doi.org/10.1016/0026-265X(88)90017-3]
(b) Pelosi, G.; Bisceglie, F.; Bignami, F.; Ronzi, P.; Schiavone, P.; Re, M.C.; Casoli, C.; Pilotti, E. Antiretroviral activity of thiosemicarbazone metal complexes. J. Med. Chem., 2010, 53(24), 8765-8769.
[http://dx.doi.org/10.1021/jm1007616] [PMID: 21121632]
(c) Youssef, N.S.; El-Seidy, A.M.A.; Schiavoni, M.; Castano, B.; Ragaini, F.; Gallo, E.; Caselli, A. Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations. J. Organomet. Chem., 2012, 714, 94-103.
[http://dx.doi.org/10.1016/j.jorganchem.2012.03.018]
(d) Palve, A.M.; Joshi, P.V.; Puranik, V.; Garje, S.S. Synthesis and X-ray single crystal structure of a cadmium (II) acetophenone thiosemicarbazone complex and its use as a single-source precursor for the preparation of CdS nanocrystallites and thin films. Polyhedron, 2013, 61, 195-201.
[http://dx.doi.org/10.1016/j.poly.2013.05.052]
(e) Palve, A.M.; Garje, S.S. Preparation of zinc sulfide nanocrystallites from single-molecule precursors. J. Cryst. Growth, 2011, 326(1), 157-162.
[http://dx.doi.org/10.1016/j.jcrysgro.2011.01.087]
[10]
(a) Gligorijević, N.; Todorović, T.; Radulović, S.; Sladić, D.; Filipović, N.; Godevac, D.; Jeremić, D.; Andelković, K. Synthesis and characterization of new Pt(II) and Pd(II) complexes with 2-quinolinecarboxaldehyde selenosemicarbazone: Cytotoxic activity evaluation of Cd(II), Zn(II), Ni(II), Pt(II) and Pd(II) complexes with heteroaromatic selenosemicarbazones. Eur. J. Med. Chem., 2009, 44(4), 1623-1629.
[http://dx.doi.org/10.1016/j.ejmech.2008.07.033] [PMID: 18789831]
(b) Todorovic, T.R.; Bacchi, A.; Sladic, D.M.; Todorovic, N.M.; Bozic, T.T.; Radanovic, D.D.; Filipovic, N.R.; Pelizzi, G.; Andelkovic, K.K. Synthesis, characterization and biological activity evaluation of Pt(II), Pd(II), Co(III) and Ni(II) complexes with N-heteroaromatic selenosemicarbazones. Inorg. Chim. Acta, 2009, 362(10), 3813-3820.
[http://dx.doi.org/10.1016/j.ica.2009.04.047]
[11]
(a) Kowol, C.R.; Eichinger, R.; Jakupec, M.A.; Galanski, M.; Arion, V.B.; Keppler, B.K. Effect of metal ion complexation and chalcogen donor identity on the antiproliferative activity of 2-acetylpyridine N,N-dimethyl(chalcogen)semicarbazones. J. Inorg. Biochem., 2007, 101(11-12), 1946-1957.
[http://dx.doi.org/10.1016/j.jinorgbio.2007.07.026] [PMID: 17825917]
(b) Shen, H.; Zhu, H.; Song, M.; Tian, Y.; Huang, Y.; Zheng, H.; Cao, R.; Lin, J.; Bi, Z.; Zhong, W. A selenosemicarbazone complex with copper efficiently down-regulates the 90-kDa heat shock protein HSP90AA1 and its client proteins in cancer cells. BMC Cancer, 2014, 14(1), 629.
[http://dx.doi.org/10.1186/1471-2407-14-629] [PMID: 25167922]
(c) Kowol, C.R.; Reisner, E.; Chiorescu, I.; Arion, V.B.; Galanski, M.; Deubel, D.V.; Keppler, B.K. An electrochemical study of antineoplastic gallium, iron and ruthenium complexes with redox noninnocent α-N-heterocyclic chalcogensemicarbazones. Inorg. Chem., 2008, 47(23), 11032-11047.
[http://dx.doi.org/10.1021/ic8013249] [PMID: 18973290]
[12]
(a) Pizzo, C.; Faral-Tello, P.; Salinas, G.; Flo, M.; Robello, C.; Wipf, P.; Mahler, S.G. Selenosemicarbazones as potent cruzipain inhibitors and their antiparasitic properties against Trypanosoma cruzi. MedChemComm, 2012, 3(3), 362-368.
[http://dx.doi.org/10.1039/c2md00283c]
(b) Pizzo, C.; Faral-Tello, P.; Yaluff, G.; Serna, E.; Torres, S.; Vera, N.; Saiz, C.; Robello, C.; Mahler, G. New approach towards the synthesis of selenosemicarbazones, useful compounds for Chagas’ disease. Eur. J. Med. Chem., 2016, 109, 107-113.
[http://dx.doi.org/10.1016/j.ejmech.2015.12.040] [PMID: 26774036]
[13]
Calcatierra, V.; López, Ó.; Fernández-Bolaños, J.G.; Plata, G.B.; Padrón, J.M. Phenolic thio- and selenosemicarbazones as multi-target drugs. Eur. J. Med. Chem., 2015, 94, 63-72.
[http://dx.doi.org/10.1016/j.ejmech.2015.02.037] [PMID: 25752525]
[14]
Chagas disease (American trypanosomiasis), Key Facts, World Health Organization., 2018. Available from: http://www.who.int/mediacentre/factsheets/fs340/en/index.html.
[15]
Al-Eisawi, Z.; Stefani, C.; Jansson, P.J.; Arvind, A.; Sharpe, P.C.; Basha, M.T.; Iskander, G.M.; Kumar, N.; Kovacevic, Z.; Lane, D.J.; Sahni, S.; Bernhardt, P.V.; Richardson, D.R.; Kalinowski, D.S. Novel mechanism of cytotoxicity for the selective selenosemicarbazone, 2-acetylpyridine 4,4-dimethyl-3-selenosemicarba- zone (Ap44mse): Lysosomal membrane permeabilization. J. Med. Chem., 2016, 59(1), 294-312.
[http://dx.doi.org/10.1021/acs.jmedchem.5b01399] [PMID: 26645570]
[16]
Filipović, N.; Polović, N.; Rašković, B.; Misirlić-Denčić, S.; Dulović, M.; Savić, M.; Nikšić, M.; Mitić, D.; Anđelković, K.; Todorović, T. Biological activity of two isomeric N-heteroaromatic selenosemicarbazones and their metal complexes. Monatsh. Chem., 2014, 145(7), 1089-1099.
[http://dx.doi.org/10.1007/s00706-014-1197-6]
[17]
Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. Reaction of lithium aluminum hydride with elemental selenium: Its application as a selenating reagent into organic molecules. J. Am. Chem. Soc., 2001, 123(34), 8408-8409.
[http://dx.doi.org/10.1021/ja005800o] [PMID: 11516295]
[18]
Bippus, P.; Molter, A.; Müller, D.; Mohr, F. Cyclohexanone selenosemicarbazone: A convenient starting material for the preparation of functionalised selenosemicarbazones and their Pt and Pd complexes. J. Organomet. Chem., 2010, 695(12-13), 1657-1662.
[http://dx.doi.org/10.1016/j.jorganchem.2010.03.029]

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