Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis
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2016
Authors
Muškinja, JovanaBurmudžija, Adrijana
Ratković, Zoran R.
Ranković, Branislav
Kosanić, Marijana
Bogdanović, Goran A.
Novaković, Slađana B.
Article (Published version)
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O-alkylated vanillin derivatives 2a-f and acetylferrocene react under Claisen-Schmidt conditions, resulting in good-to-high yields of the corresponding ferrocene chalcones 3a-f. None of the resultant compounds 3b-f has been previously described in the literature. All synthesized compounds were characterized by spectral and physical data, whereas two of them, 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)-prop-2-en-1-one (3b) and 1-ferrocenyl-3-(4-buthoxy-3-methoxy-phenyl)-prop-2-en-1-one (3e), were crystalline substances, suitable for single-crystal X-ray analysis, which confirmed undoubtedly their structures. Chalcones 3a-f were tested for their biological activity and demonstrated relatively good in vitro antimicrobial activity towards different strains of bacteria and fungi. The best antibacterial activity is expressed by compounds 3b and 3c, while compound 3d shows the best antifungal activity.
Keywords:
Vanillin / Ferrocene / Ferrocenyl chalcones / Microbial activity / Crystal structureSource:
Medicinal Chemistry Research, 2016, 25, 9, 1744-1753Funding / projects:
- Novel Electrochemical and Chemical Methods in Synthesis of Organic Compounds of Interest for Medicine and Material Chemistry (RS-MESTD-Basic Research (BR or ON)-172034)
- Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds (RS-MESTD-Basic Research (BR or ON)-172014)
DOI: 10.1007/s00044-016-1609-8
ISSN: 1054-2523; 1554-8120
WoS: 000385175500002
Scopus: 2-s2.0-84976471899
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VinčaTY - JOUR AU - Muškinja, Jovana AU - Burmudžija, Adrijana AU - Ratković, Zoran R. AU - Ranković, Branislav AU - Kosanić, Marijana AU - Bogdanović, Goran A. AU - Novaković, Slađana B. PY - 2016 UR - https://vinar.vin.bg.ac.rs/handle/123456789/1268 AB - O-alkylated vanillin derivatives 2a-f and acetylferrocene react under Claisen-Schmidt conditions, resulting in good-to-high yields of the corresponding ferrocene chalcones 3a-f. None of the resultant compounds 3b-f has been previously described in the literature. All synthesized compounds were characterized by spectral and physical data, whereas two of them, 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)-prop-2-en-1-one (3b) and 1-ferrocenyl-3-(4-buthoxy-3-methoxy-phenyl)-prop-2-en-1-one (3e), were crystalline substances, suitable for single-crystal X-ray analysis, which confirmed undoubtedly their structures. Chalcones 3a-f were tested for their biological activity and demonstrated relatively good in vitro antimicrobial activity towards different strains of bacteria and fungi. The best antibacterial activity is expressed by compounds 3b and 3c, while compound 3d shows the best antifungal activity. T2 - Medicinal Chemistry Research T1 - Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis VL - 25 IS - 9 SP - 1744 EP - 1753 DO - 10.1007/s00044-016-1609-8 ER -
@article{ author = "Muškinja, Jovana and Burmudžija, Adrijana and Ratković, Zoran R. and Ranković, Branislav and Kosanić, Marijana and Bogdanović, Goran A. and Novaković, Slađana B.", year = "2016", abstract = "O-alkylated vanillin derivatives 2a-f and acetylferrocene react under Claisen-Schmidt conditions, resulting in good-to-high yields of the corresponding ferrocene chalcones 3a-f. None of the resultant compounds 3b-f has been previously described in the literature. All synthesized compounds were characterized by spectral and physical data, whereas two of them, 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)-prop-2-en-1-one (3b) and 1-ferrocenyl-3-(4-buthoxy-3-methoxy-phenyl)-prop-2-en-1-one (3e), were crystalline substances, suitable for single-crystal X-ray analysis, which confirmed undoubtedly their structures. Chalcones 3a-f were tested for their biological activity and demonstrated relatively good in vitro antimicrobial activity towards different strains of bacteria and fungi. The best antibacterial activity is expressed by compounds 3b and 3c, while compound 3d shows the best antifungal activity.", journal = "Medicinal Chemistry Research", title = "Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis", volume = "25", number = "9", pages = "1744-1753", doi = "10.1007/s00044-016-1609-8" }
Muškinja, J., Burmudžija, A., Ratković, Z. R., Ranković, B., Kosanić, M., Bogdanović, G. A.,& Novaković, S. B.. (2016). Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis. in Medicinal Chemistry Research, 25(9), 1744-1753. https://doi.org/10.1007/s00044-016-1609-8
Muškinja J, Burmudžija A, Ratković ZR, Ranković B, Kosanić M, Bogdanović GA, Novaković SB. Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis. in Medicinal Chemistry Research. 2016;25(9):1744-1753. doi:10.1007/s00044-016-1609-8 .
Muškinja, Jovana, Burmudžija, Adrijana, Ratković, Zoran R., Ranković, Branislav, Kosanić, Marijana, Bogdanović, Goran A., Novaković, Slađana B., "Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis" in Medicinal Chemistry Research, 25, no. 9 (2016):1744-1753, https://doi.org/10.1007/s00044-016-1609-8 . .