Synthesis, Characterization, Antimicrobial and Antimalarial Activities of 5-((2- phenylacetoxy) carbonyl)-1H-pyrazole-3-carboxylic Acid and its Ce(III), Pr(III) and Nd(III) Complexes

http://www.doi.org/10.26538/tjnpr/v7i5.28

Authors

  • Adejoh Ocheni Department of Pure and Industrial Chemistry, Kogi State University, Anyigba, Nigeria
  • Pius O. Ukoha Department of Chemistry, University of Nigeria, Nsukka, Nigeria

Keywords:

antimalarial, Plasmodium falciparum, Lanthanoid(III), Pyrazole

Abstract

In the past decade, the lanthanoid coordination chemistry was one of the most focused areas of research due to their wide applications as catalyst, magnetism, luminescence and diagnostic tools in biological studies. In this study, novel pyrazole; 5-((2-phenylacetoxy) carbonyl)-1Hpyrazole-3-carboxylic acid derivative and its lanthanoid complexes are designed and tested for potential antimicrobial and antimalarial activities. The binuclear ligand bridge complexes were obtained by the interaction of the ligand with the lanthanide salts. The compounds were characterized by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, UltravioletVisible spectroscopy, Fourier Transform infrared (FT-IR) spectroscopy, Mass spectrometry (MS), Elemental analysis and Magnetic susceptibility measurements. The in vitro antimicrobial assay was done by Agar well diffusion method and in vivo antimalarial studies were performed based on Peter’s method. The results were analysed using one way analysis of variance (ANOVA). The antimicrobial and antiparasitic effects of these compounds were found to be dose-dependent and they showed greater effects at higher doses. 

References

Manfredini S, Bazzanini R, Baraldi PG, Guarneri M, Simoni D, Marongiu ME, Pani A, Colla P, Tramontano E. Pyrazolerelated nucleosides. Synthesis and antiviral/antitumor activity of some substituted pyrazole and pyrazolo[4,3-d]- 1,2,3-triazin-4-one nucleosides. J Med Chem. 1992; 35: 917–924.

Komeda S, Lutz M, Spek AL, Chikuma M, Reedijk J. New antitumor-active azole-bridged dinuclear platinum(II) complexes: synthesis, characterization, crystal structures and cytotoxic studies. Inorg Chem. 2000;39:4230–4236.

Gamage S.A, Spicer JA, Rewcastle GW, Milton J, Sohal S, Dangerfield W, Mistry P, Vicker N, Charlton PA, Denny WA. Structure–activity relationships for pyrido-imidazopyrazolo-, pyrazino-, and pyrrolophenazinecarboxamides as topoisomerase-targeted anticancer agents.J Med Chem. 2002; 45:740–743.

Moukha-chafiq O, Taha ML, Lazrek HB, Vasseur JJ, Pannecouque C, Witvrouw M, De Clercq E.Synthesis and biological activity of some 4-substituted 1-[1-(2,3- dihydroxy-1-propoxy)methyl-1,2,3-triazol- (4&5)-ylmethyl]-1H-pyrazolo[3,4-d]pyrimidines. Farmaco. 2002; 57: 27–32 DOI org/10.1016/S0014-827X(01)01152- 1).

Rostom SAF, Shalaby MA, El-Demellawy MA. Polysubstituted pyrazoles, part 5. Synthesis of new 1-(4- chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti -HCV agents. Eur J Med Chem. 2003; 38:959–974.

Duivenvoorden WCM, Liu YN, Schatte G, Kraatz HB. Synt hesis of redox active ferrocene pyrazole conjugates and their cytotoxicity in human mammary adenocarcinoma MCF-7 cells. Inorg Chim Acta. 2005;358:3183–3189.

Park HJ, Lee K, Park SJ, Ahn B, Lee JC, Cho HY, Lee KI. Identification of antitumor activity of pyrazole oxime ethers. Bioorg Med Chem Lett. 2005;15:3307–3312.

Keter FK, Nell MJ, Omondi B, Guzei IA, Darkwa J. Anticancer activities of bis(pyrazol-1-ylthiocarbonyl) disulfides against HeLa cells. J Chem Res. 2009; 5:322– 325.

Frankline KK and James D. Perspective: The potential of pyrazole- based compounds in medicine. An Int J on role of metal ions in Biol, Biochem Med. 2012; 25(1):9-21.

Arianie L, Supriatna MI, Kazal N, Widodo N, Warsito W, Iftitah ED. Synthesis, In vitro, and In silico Studies of

Methyl Eugenol Derivatives for Plasmodium falciparum Inhibitor. Trop J Nat Prod Res. 2022; 6(9):1446–1454.

Dominguez JN, Jaime EC, Mario C, Flavia R. Synthesis and antimalerial activity of substituted pyrazole derivatives. Arzneimittelforschung.2002; 52(6): 482- 488.

Bekhit AA and ALaa EB. Synthesis, insilico experiments and biological evaluation of 1, 3,4-trisubstituted pyrazole derivatives as antimalarial agent. Eur J Med Chem. 2019; 163: 353-366.

Roderick JS and Ann A. Diacid-substituted heteroanyl derivative as matrix metallo proteainase inhibitors limited state patent. US Patent Authority 1sted United state patent.pub. no 20030087924A1 United State 2003

Jie Y, Jia-Neng J, Yanbng G. Lactic acid as an invaluable bio-based solvent for organic reactions. Electronic supporting information. Green Chem. 2012; 14(12):3304- 3317.

Heinosuke Y. Infrared Analysis of 2-pyrazolin-5- one derivatives. Appl Spectrosc. 1967; 23(1):22-28.

Balouiri M, Sadiki M, Ibnsouda SK. Methods for invitro evaluating antimicrobial activity: A reviewJ Pharm Anal. 2016;6(2):71-79.

Peter W, Portus H, Robinson L. The four-day suppressive in vivo anti-malarial test. Ann Trop Med Parasitol.1975; 69:155-171.

Siddappa K, Shikkargol RK, Angadi SD. Synthesis characterization, thermal and electrical conductance studies of La(III) complexes with 3-substituted triazole Schiff base. Proc. Indian Natn Sci. Acad. 2009; 75(2):73-77.

Muliadi S, Suminar P, Alfian N, Indah R.The uv-visible, infrared spectra and luminescence analysis of lanthanum(III) and neodymium(III) (diphenyl amino)3-(2,2- bipyridyl) complexes. Int J Appl Engr Res. 2018; 13(6):4049-4052.

Qingrui Z, Xiuyun Y, Ruiping D, Liang Z, Yang Y, Yunhui L. Synthesis and near infrared luminescence properties of series of lanthanide complexes with POSS modified ligands. Mol. 2019; 24(7):1253.

Obasi LN, Oruma US, Al-Swaidan IA, Ramasami P, Ezeorah CJ,Ochonogor AE. Synthesis characterization and antibacterial studies of N-

(benzothiazol-2-yl)-4-chlorobenzenesulphonamide and its neodymium(III) and thallium(III) complexes. Mol. 2017; 22(153):1-11.

Ptaszyński AZ. Synthesis and Properties of Solid Complexes of Lanthanum, Cerium, Neodymium and Erbium with

Phosphonomethylglycine. Polish J Environ Stud. 2001; 10(4):257-262.

Maharudra K, Vikas V, Jagdish T. Studies and Synthesis of Biologically Active Mixed Ligand Cerium (III) Complexes.Int J Sci Res. 2012; 2319-7064.

Chithambarathanu T, Umayorubaghan V, Krishnakumar V. Vibrational analysis of some pyrazole derivatives. Ind J Pure Appl Phy. 2003; 41:844 - 848.

Robert MS, Francis XW, David JK. Spectrometric identifica tion of organic compounds.7th ed. John Wiley and sons.Inc. 2005. 86-101 p.

Guskos N, Paschalidis DG, Majszczyk J, Typek J, Maryniak M. Photoacoustic study of a new neodymium(III) hydrazone complex.Mat Sci-Pol. 2005; 23( 4):1030-1034.

Keshavena B and Chandrashekara PG. C omplexes of Lanthanide(III) nitrate with 10- (2-dimethylamino-1-methyl phenothiazine. Proc Ind Acad Sci.(Chem Sci). 1998; 110 (6):527-534.

Kuppusamy S and Chinniagounder T.Studies of Cerium III Complexes of Piperidin-4-one.Ind J Chem. 2002; 41A:1417-1420.

Kumar G O, Tanwer J, Kumar M, Akhter S, Sharma CR, Pillai MM, Alam MS. Pyrazole-pyrazoline as promising novel antimalarial agents: A mechanistic study.Eur J Med Chem. 2018; 149:139-147.

Patricia G, Samia B, Antonio H, Christian C, Carlos R, Joseph C, Andrés C, Carlos, JG. Tuning the structure and properties of lanthanoid coordination polymers with an symmetric anilato ligand. Magnetochem.2018; 4(6):1-21D.

Haddad BS. Synthesis, Characterization and Biological Studies of Some New Dinitrone Compounds: Trop J Nat Prod Res. 2022;6(11):1836–1839.

Published

2023-06-01

How to Cite

Ocheni, A., & Ukoha, P. O. (2023). Synthesis, Characterization, Antimicrobial and Antimalarial Activities of 5-((2- phenylacetoxy) carbonyl)-1H-pyrazole-3-carboxylic Acid and its Ce(III), Pr(III) and Nd(III) Complexes: http://www.doi.org/10.26538/tjnpr/v7i5.28. Tropical Journal of Natural Product Research (TJNPR), 7(5), 3028–3033. Retrieved from https://tjnpr.org/index.php/home/article/view/1987