Synthesis, in vitro evaluation of antibacterial, antifungal and larvicidal activities of pyrazole/pyridine based compounds and their nanocrystalline MS (M = Cu and Cd) derivatives
- 159 Downloads
Methyl 3,5-dimethyl pyrazole-1-dithioate (mdpa) (1), benzyl 3,5-dimethyl pyrazole-1-dithioate (bdpa) (2), 3,5-dimethylpyrazole-1-(5methyl-1H-pyrazol-3-ylmethyl)-1H-pyrazole (3), copper(II)-mdpa (4), copper(II)-bdpa (5), cadmium(II)-mdpa (6), cadmium(II)-bdpa (7), Cu2S nanoparticles (8 and 9) derived from 4 and 5, respectively, CdS nanoparticles (10 and 11) derived from 6 and 7, respectively, were synthesized to screen their antimicrobial activities. Prolonged reaction with CuCl2.2H2O and 3 followed by addition of trace amount of pyridine furnished a crystalline chloro bridged complex [Cu(μ-Cl)2(pyridine)2]n and its structure was solved by single X-ray crystallography. Antibacterial activities of all of the synthesized materials (1–12) were evaluated against Gram positive bacteria including Staphylococcus aureus and Bacillus subtilis and Gram negative bacteria including Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae and Proteus vulgaris. Fungi (Candida albicans, Aspergillus flavus) were also used to test antifungal activities with the compounds. Present study revealed that 8 shows best antibacterial activity among the present reported compounds. An excellent antifugal activity is shown by 12 emerging to be a better antibiotic than standard fluconazole. Besides fungicidal effect, 12 has promising larvicidal effect. The structure and activity relationship has been discussed.
KeywordsAntibacterial Antifungal Larvicidal Pyrazole/Pyridine complexes Nanoparticles
This investigation was supported by University grants Commission (UGC), Government of India for financial support (ref. grant no.-42-280/2013(SR)) and Council for Scientific and Industrial Research (CSIR) for the project grant (No.1(2858)/16/EMR-II). We are also thankful to Dr. Nandan Bhattacharyya, Principal, Panskura Banamali College, for providing instruments for biological assay.
Compliance with ethical standards
Conflict of interest
The authors declare that they have no competing interests.
- Albada GA, Horst MG, Mutikainen I, Turpeinen U, Reedijk J (2008) New 3,5-dimethylpyrazole copper(II) compounds with a variety of hydrogen bonds, synthesized by using a dehydrating agent: Synthesis, characterization, structures and intermolecular interactions. Inorg Chim Acta 361:3380–3387CrossRefGoogle Scholar
- Bruker, SAINT (Version 6.28a) and SADABS (Version 2.03) (2001) Data reduction and absorption correction program. Bruker AXS Inc, Madison, WisconsinGoogle Scholar
- Bruker, SMART (Version 5.625) (2001) Data collection program. Bruker AXS Inc., Madison, WisconsinGoogle Scholar
- Camargo TP, Maia FF, Chaves C, de Souza B, Bortoluzzi AJ, Castilho N, Bortolotto T, Terenzi H, Castellano EE, Haase W, Tomkowicz Z, Peralta RA, Neves A (2015) Synthesis, characterization, hydrolase and catecholase activity of a dinuclear iron(III) complex: catalytic promiscuity. J Inorg Biochem 146:77–88CrossRefPubMedGoogle Scholar
- Malvar DC, Ferreira RT, de Castro RA, de Castro LL, Freitas AC, Costa EA, Florentino IF, Mafra JC, de Souza GE, Vanderlinde FA (2014) Antinociceptive, anti-inflammatory and antipyretic effects of 1,5-diphenyl-1H-Pyrazole-3-carbohydrazide, a new heterocyclic pyrazole derivative. Life Sci 95(2):81–88CrossRefGoogle Scholar
- Mondal G, Santra A, Bera P, Acharjya M, Jana S, Chattopadhyay D, Mondal A, Seok SI, Bera P (2016) A pyrazolyl-based thiolato single-source precursor for the selective synthesis of isotropic copper-deficient copper(I) sulfide nanocrystals: synthesis, optical and photocatalytic activity. J Nanopart Res 18:311. doi: 10.1007/s11051-016-3538-3 CrossRefGoogle Scholar
- Mowbray CE, Braillard S, Speed W, Glossop PA, Whitlock GA, Gibson KR, Mills JE, Brown AD, Gardner JM, Cao Y, Hua W, Morgans GL, Feijens PB, Matheeussen A, Maes LJ (2015) Novel amino-pyrazole ureas with potent in vitro and in vivo antileishmanial activity. J Med Chem 58(24):9615–9624CrossRefPubMedGoogle Scholar
- Porcari AR, Devivar RV, Kucera LS, Drach JC, Townsend LB (1998) Design, synthesis, and antiviral evaluations of 1-(substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as nonnucleoside analogues of 2,5,6-trichloro-1-(b-D-ribofuranosyl)benzimidazole. J Med Chem 41:1252–1262CrossRefPubMedGoogle Scholar
- Sheldrick GM (2001) SHELXTL (Version 6.12) Structure Analysis Program. Bruker AXS Inc, Madison, WisconsinGoogle Scholar
- Vanden Berghe DA, Vlietinck AJ (1991) Screening methods for antibacterial and antiviral agents from higher plants. In: Dey PMp, Harbone J B (eds) Methods in plant biochemistry. Academic, London, p 47–69Google Scholar