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Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties

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2018
Authors
Burmudzija, Adrijana
Muskinja, Jovana
Ratković, Zoran R.
Kosanić, Marijana
Ranković, Branislav
Novaković, Slađana B.
Bogdanović, Goran A.
Article
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Abstract
A series of ferrocenyl ketones were synthesized in reaction with ferrocene and corresponding substituted acryloyl chlorides, following previously described procedure. Synthesized products have conjugated enone system, which is suitable for further transformations. In a reaction with hydrazine in acidic medium (acetic acid) new pyrazoline derivatives were obtained. Their antimicrobial properties have been tested. Synthesized pyrazoline derivatives demonstrated expressed in vitro antimicrobial activity towards 12 strains of microorganisms inhibiting all tested bacteria and fungi. The most potent compound in all cases was sorbyl derivative; for bacteria activity was very close to streptomycin, and for fungi in one case the same as ketoconazole. It is established that this compound can be a new, potential antimicrobial agent with minimum inhibitory concentrations from 0.039 to 0.312 mg/mL. One of the starting compounds and two products were crystal substances, suitable for the single cryst...al X-ray diffraction analysis, which confirmed undoubtedly their structures. (C) 2017 Elsevier B.V. All rights reserved.

Keywords:
Ferrocenyl ketones / Enone system / Pyrazoline derivatives / Crystal structure / Antimicrobial activity
Source:
Inorganica Chimica Acta, 2018, 471, 570-576
Funding / projects:
  • Novel Electrochemical and Chemical Methods in Synthesis of Organic Compounds of Interest for Medicine and Material Chemistry (RS-172034)
  • Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds (RS-172014)

DOI: 10.1016/j.ica.2017.11.061

ISSN: 0020-1693; 1873-3255

WoS: 000419826000073

Scopus: 2-s2.0-85037338796
[ Google Scholar ]
8
8
URI
https://vinar.vin.bg.ac.rs/handle/123456789/1910
Collections
  • WoS Import
Institution/Community
Vinča
TY  - JOUR
AU  - Burmudzija, Adrijana
AU  - Muskinja, Jovana
AU  - Ratković, Zoran R.
AU  - Kosanić, Marijana
AU  - Ranković, Branislav
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1910
AB  - A series of ferrocenyl ketones were synthesized in reaction with ferrocene and corresponding substituted acryloyl chlorides, following previously described procedure. Synthesized products have conjugated enone system, which is suitable for further transformations. In a reaction with hydrazine in acidic medium (acetic acid) new pyrazoline derivatives were obtained. Their antimicrobial properties have been tested. Synthesized pyrazoline derivatives demonstrated expressed in vitro antimicrobial activity towards 12 strains of microorganisms inhibiting all tested bacteria and fungi. The most potent compound in all cases was sorbyl derivative; for bacteria activity was very close to streptomycin, and for fungi in one case the same as ketoconazole. It is established that this compound can be a new, potential antimicrobial agent with minimum inhibitory concentrations from 0.039 to 0.312 mg/mL. One of the starting compounds and two products were crystal substances, suitable for the single crystal X-ray diffraction analysis, which confirmed undoubtedly their structures. (C) 2017 Elsevier B.V. All rights reserved.
T2  - Inorganica Chimica Acta
T1  - Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties
VL  - 471
SP  - 570
EP  - 576
DO  - 10.1016/j.ica.2017.11.061
ER  - 
@article{
author = "Burmudzija, Adrijana and Muskinja, Jovana and Ratković, Zoran R. and Kosanić, Marijana and Ranković, Branislav and Novaković, Slađana B. and Bogdanović, Goran A.",
year = "2018",
abstract = "A series of ferrocenyl ketones were synthesized in reaction with ferrocene and corresponding substituted acryloyl chlorides, following previously described procedure. Synthesized products have conjugated enone system, which is suitable for further transformations. In a reaction with hydrazine in acidic medium (acetic acid) new pyrazoline derivatives were obtained. Their antimicrobial properties have been tested. Synthesized pyrazoline derivatives demonstrated expressed in vitro antimicrobial activity towards 12 strains of microorganisms inhibiting all tested bacteria and fungi. The most potent compound in all cases was sorbyl derivative; for bacteria activity was very close to streptomycin, and for fungi in one case the same as ketoconazole. It is established that this compound can be a new, potential antimicrobial agent with minimum inhibitory concentrations from 0.039 to 0.312 mg/mL. One of the starting compounds and two products were crystal substances, suitable for the single crystal X-ray diffraction analysis, which confirmed undoubtedly their structures. (C) 2017 Elsevier B.V. All rights reserved.",
journal = "Inorganica Chimica Acta",
title = "Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties",
volume = "471",
pages = "570-576",
doi = "10.1016/j.ica.2017.11.061"
}
Burmudzija, A., Muskinja, J., Ratković, Z. R., Kosanić, M., Ranković, B., Novaković, S. B.,& Bogdanović, G. A.. (2018). Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties. in Inorganica Chimica Acta, 471, 570-576.
https://doi.org/10.1016/j.ica.2017.11.061
Burmudzija A, Muskinja J, Ratković ZR, Kosanić M, Ranković B, Novaković SB, Bogdanović GA. Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties. in Inorganica Chimica Acta. 2018;471:570-576.
doi:10.1016/j.ica.2017.11.061 .
Burmudzija, Adrijana, Muskinja, Jovana, Ratković, Zoran R., Kosanić, Marijana, Ranković, Branislav, Novaković, Slađana B., Bogdanović, Goran A., "Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties" in Inorganica Chimica Acta, 471 (2018):570-576,
https://doi.org/10.1016/j.ica.2017.11.061 . .

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