Cadmium(II) Schiff base Complex Containing 5-Fluoroisatin Moiety: Synthesis, Characterization, Antibacterial Activity and Structural Studies

Authors

  • Mohd Abdul Fatah Abdul Manan Faculty of Applied Sciences, Universiti Teknologi MARA, 40450, Shah Alam, Selangor, Malaysia
  • David Bradford Cordes EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, United Kingdom

DOI:

https://doi.org/10.48048/tis.2022.5796

Keywords:

Cadmium(II), Dithiocarbazate, 5-fluoroisatin, Single-crystal structure, Antibacterial

Abstract

The Schiff base ligand, HSB5FISA (H1), obtained by the condensation of S-benzyldithiocarbazate with 5-fluoroisatin, has been employed to synthesize a new cadmium(II) complex, Cd(SB5FISA)2 (2) (SB5FISA = monoanionic form of H1). The complex has been characterized by elemental analysis, molar conductivity, magnetic susceptibility, inductively coupled plasma atomic emission spectroscopy (ICP-AES), Fourier-transform infrared spectroscopy (FT-IR) and ultraviolet-visible spectroscopy (UV-Vis). The crystallographic study of Cd(SB5FISA)2×2DMSO (2a) (DMSO = dimethyl sulfoxide) was conducted using single-crystal X-ray diffraction. The crystal structure of 2a confirmed the presence of 6-coordinated cadmium in a distorted octahedral environment. Ligand H1 behaves in a tridentate monoanionic fashion, coordinating to a cadmium(II) metal centre through the thiolate sulfur, azomethine nitrogen and carbonyl oxygen. The antibacterial activity of both H1 and 2 was examined against 4 different bacterial strains using the disc diffusion method. Complex 2 showed significant inhibitory effect against Bacillus subtilis with an inhibition zone of 14 mm, comparable to the standard antibiotic streptomycin.

HIGHLIGHTS 

  • Cd(II) complex of 5-fluoroisatin Schiff base was synthesized
  • Structural studies of compound determined via single crystal X-ray diffraction
  • Compound exhibited significant antibacterial activity towards Bacillus subtilis


GRAPHICAL ABSTRACT

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

References

Y Zhu, J Han, J Wang, N Shibata, M Sodeoka, VA Soloshonok, JA Coelho and FD Toste. Modern approaches for asymmetric construction of carbon-fluorine quaternary stereogenic centers: Synthetic challenges and pharmaceutical needs. Chem. Rev. 2018; 7, 3887-964.

Y Ogawa, E Tokunaga, O Kobayashi, K Hirai and N Shibata. Current contributions of organofluorine compounds to the agrochemical industry. iScience 2020; 23, 101467.

N Xu, J Shi, G Liu, X Yang, J Zheng, Z Zhang and Y Yang. Research progress of fluorine-containing electrolyte additives for lithium ion batteries. J. Power Sources Adv. 2021; 7, 100043.

A Haider, L Gobbi, J Kretz, C Ullmer, A Brink, M Honer, TJ Woltering, D Muri, H Iding, M Bürkler, M Binder, C Bartelmus, I Knuesel, P Pacher, AM Herde, F Spinelli, H Ahmed, K Atz, C Keller, M Weber, R Schubli, L Mu, U Grether and SM Ametamey. Identification and preclinical development of a 2,5,6-trisubstituted fluorinated pyridine derivative as a radioligand for the positron emission tomography imaging of cannabinoid type 2 receptors. J. Med. Chem. 2020; 63, 10287-306.

J Han, AM Remete, LS Dobson, L Kiss, K Izawa, H Moriwaki, VA Soloshonok and D O’Hagan. Next generation organofluorine containing blockbuster drugs. J. Fluorine Chem. 2020; 239, 109639.

D O’Hagan. Understanding organofluorine chemistry. An introduction to the C-F Bond. Chem. Soc. Rev. 2008; 37, 308-19.

MAFA Manan, DB Cordes, AMZ Slawin, M Bühl, VWY Liao, HC Chua, M Chebib and D O’Hagan. The synthesis and evaluation of fluoro-, trifluoromethyl-, and iodomuscimols as GABA agonists. Chem. Eur. J. 2017; 23, 10848-52.

NA Meanwell. Fluorine and fluorinated motifs in the design and application of bioisosteres for drug design. J. Med. Chem. 2018; 61, 5822-80.

Q Wu, JC Xiao, C Zhou, JR Sun, MF Huang, X Xu, T Li and H Tian. Crystal structure and supramolecular architecture of inorganic ligand-coordinated salen-type Schiff base complex: Insights into halogen bond from theoretical analysis and 3D energy framework calculations. Crystals 2020; 10, 334.

P Basu, S Riyajuddin, TK Dey, A Ghosh, K Ghosh and SM Islam. Synthesis and architecture of polystyrene-supported Schiff base-palladium complex: Catalytic features and functions in diaryl urea preparation in conjunction with Suzuki-Miyaura cross-coupling reaction by reductive carbonylation. J. Organomet. Chem. 2018; 877, 37-50.

X Liu, C Manzur, N Novoa, S Celedón, D Carrillo and JR Hamon. Multidentate unsymmetrically-substituted Schiff bases and their metal complexes: Synthesis, functional materials properties, and applications to catalysis. Coord. Chem. Rev. 2018; 357, 144-72.

MAFA Manan, MIM Tahir, KA Crouse and FNF How. Distorted octahedral S-methyl2-(2-oxoindolin-3-ylidene) hydrazinecarbodithioate (SMISA) tridentate Schiff base complex of Co(II): Synthesis, characterization and structural studies. Malaysian J. Chem. 2020; 22, 25.

E Zangrando, MT Islam, MAAA Islam, MC Sheikh, MTH Tarafder, R Miyatake, R Zahan and MA Hossain. Synthesis, characterization and bio-activity of nickel (II) and copper (II) Complexes of a bidentate NS Schiff base of S-benzyldithiocarbazate. Inorg. Chim. Acta 2015; 427, 278-284.

A Hameed, M Al-Rashida, M Uroos, SA Ali and KM Khan. Schiff bases in medicinal chemistry: A patent review (2010 - 2015). Expert Opin. Ther. Pat. 2017; 27, 63-79.

X Liu and Hamon JR. Recent developments in penta-, hexa-and heptadentate schiff base ligands and their metal complexes. Coor. Chem. Rev. 2019; 404, 213109.

AZ El-Sonbati, WH Mahmoud, GG Mohamed, MA Diab, SM Morgan and SY Abbas. Synthesis, characterization of schiff base metal complexes and their biological investigation. Appl. Organomet. Chem. 2019; 33, e5048.

R Nath, S Pathania, G Grover and MJ Akhtar. Isatin containing heterocycles for different biological activities: Analysis of structure activity relationship. J. Mol. Struct. 2020; 1222, 128900.

MAFA Manan, KA Crouse, MIM Tahir, R Rosli, FNF How, DJ Watkin and AMZ Slawin. Synthesis, characterization and cytotoxic activity of s-benzyldithiocarbazate schiff bases derived from 5-fluoroisatin, 5-chloroisatin, 5-bromoisatin and their crystal structures. J. Chem. Crystallogr. 2011; 41, 1630-41.

GM Sheldrick. SAINT V4 software reference manual. Siemens Analytical X-ray Systems, Madison, Wisconsin, 1996.

GM Sheldrick. Program for empirical absorption correction of area detector data. University of Göttingen, Göttingen, Germany, 1996.

MC Burla, R Caliandro, M Camalli, B Carrozzini, GL Cascarano, C Giacovazzo, M Mallamo, A Mazzone, G Polidori and R Spagna. R. SIR2011: A new package for crystal structure determination and refinement. J. Appl. Crystallogr. 2012; 45, 357-61.

GM Sheldrick. Crystal structure refinement with SHELXL. Acta Crystallogr. C 2015; 71, 3-8.

OV Dolomanov, LJ Bourhis, RJ Gildea, JAK Howard and H Puschmann. OLEX2: A complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009; 42, 339-41.

AW Bauer. Antibiotic susceptibility testing by a standardized single disk method. Am. J. Clin. Pathol. 1966; 45, 493-6.

R Takjoo, R Centore and SS Hayatolgheibi. Mixed ligand complexes of cadmium (II) and copper (II) dithiocarbazate: Synthesis, spectral characterization, x-ray crystal structure. Inorg. Chim. Acta. 2018; 471, 587-94.

A Banerjee, M Mohanty, S Lima, R Samanta, E Garribba, T Sasamori and R Dinda. Synthesis, structure and characterization of new dithiocarbazate-based mixed ligand oxidovanadium(IV) complexes: DNA/HSA interaction, cytotoxic activity and DFT studies. New J. Chem. 2020; 44, 10946-63.

E Labisbal, A Sousa-Pedrares, W Kaminsky and DX West. Structure of N-methylisatin N(4)-dimethylthiosemicarbazone and its electrochemically synthesized 6-coordinate cadmium(II) complex. Z. Naturforsch. B 2002; 57, 908-13.

E Labisbal, A Sousa, A Castiñeiras, JA García-Vázquez, J Romero, GA Bain and DX West. Electrochemical synthesis of a 6-coordinate cadmium(II) complex with N-methylisatin N(4)-cyclohexylthiosemicarbazone. Zeitschrift für Naturforschung B 2000; 55, 162-6.

VS Nogueira, L Bresolin, C Näther, I Jess and ABD Oliveira. Crystal structure of cis-bis­{4-phenyl-1-[(3R)-1,7,7-tri­methyl-2-oxobicyclo­[2.2.1]heptan-3-ylidene]thiosemicarbazidato κ3O,N1,S}= cadmium(II) with an unknown solvent molecule. Acta Crystallogr. Sect. E. 2015; 71, m234 - m235.

KB Chew, MTH Tarafder, KA Crouse, AM Ali, BM Yamin and HK Fun. Synthesis, characterization and bio-activity of metal complexes of bidentate N–S isomeric Schiff bases derived from S-methyldithiocarbazate (SMDTC) and the X-ray structure of the bis[S-methyl-β-N-(2-furyl-methylketone)dithiocarbazato]cadmium(II) complex. Polyhedron 2004; 23, 1385-92.

ZH Chohan, A Munawar and Ct Supuran. Transition metal ion complexes of schiff-bases. Synthesis, characterization and antibacterial properties. Met. Based Drug. 2001; 8, 137-143.

MA Malik, OA Dar, P Gull, MY Wani and AA Hashmi. Heterocyclic Schiff base transition metal complexes in antimicrobial and anticancer chemotherapy. MedChemComm. 2018; 9, 409-436.

Downloads

Published

2022-08-28

How to Cite

Manan, M. A. F. A. ., & Cordes, D. B. . (2022). Cadmium(II) Schiff base Complex Containing 5-Fluoroisatin Moiety: Synthesis, Characterization, Antibacterial Activity and Structural Studies . Trends in Sciences, 19(18), 5796. https://doi.org/10.48048/tis.2022.5796