Araştırma Makalesi
BibTex RIS Kaynak Göster

Synthesis, E/Z isomerisation and antimicrobial studies of different structured novel ketone derivatives.

Yıl 2019, Cilt: 6 Sayı: 2, 177 - 188, 15.06.2019
https://doi.org/10.18596/jotcsa.486487

Öz

In this study five different structured mono ketones’
(k1- k5) novel derivatives as five
new   hydrazones (h1-h5) and   five new
semicarbazones (s1-s5) were
synthesized.  The synthesized compounds
were identified by IR, 1H-NMR, 13C-NMR, mass and
chromatographic methods for their structures and E/Z isomerizations.  These mentioned hydrazones and semicarbazones
were investigated for their antimicrobial activities.  Seven bacterias and three fungis were tested.
Ciprofloxacin and Fluconazole were used as standards. MIC values were
determined. The relationship between structure and antimicrobial actvity was
discussed. Hydrazones were more effective than semicarbazones. Besides, acetyl
acetone as a diketone delivered the known
1-(2,4-dinitrophenyl)-3,5-dimethyl-1H-pyrazole (p1) which showed very high antimicrobial activity than hydrazones
and semicarbazones against Klebsiella
pneumoniae
ATCC 4352, Proteus mirabilis
ATCC 14153, Staphylococcus epidermidis
ATCC 12228, Enterococcus faecalis
ATCC 29212, Candida parapsilosis ATCC
22019, Candida tropicalis ATCC 750.

Kaynakça

  • 1. Reddy KH, Reddy PS, Babu PR, (2000) Nuclease activity of 2-substituted heteroaromatic thiosemicarbazone and semicarbazone copper (II) complexes.Transition Metal Chemistry 25, 154-160.
  • 2. Babahan I, Coban EP, Biyik H, (2013) Synthesis, characterization and antimicrobial activities of vic-dioxime derivatives containing heteroaromatic hydrazine groups and their metal complexes.Maejo International Journal of Science and Technology 7:01, 26-41.
  • 3. Enyedy EA, Bognar GM, Nagy NV, Jakusch T, Kiss T, (2014) Solution speciation of potential anticancer metal complexes of salicylaldehyde semicarbazone and its bromo derivative.Polyhedron 67, 242-252.
  • 4. Kiasat AR, Kazemi F, Mehrjardi MF, (2007) Basic alumina as an efficient catalyst for preparation of semicarbazones in solvent free conditions. Journal of Chinese Chemical Society 54, 1337-1339.
  • 5. Sameem S, Kumar N, Pathak D, (2012) Synthesis and anticonvulsant activity of some newer semicarbazone derivatives. International Journal of Pharmaceutical Sciences and Drug Research 4:3, 195-198.
  • 6. Gup R, (2013), Synthesis and spectroscopic studies of new bis-acylhydrazone compounds. Chimica acta Turcica 35:1, 55-61.
  • 7. Torje IA, Valean AM, Cristea C, (2012) Phenothiazine-carboxaldehyde-hydrazone derivatives, synthesis, characterisation and electronic properties. Academia Romana 57:4-5, 337-344.
  • 8. Hu J, Chen S, Sun Y, Yang J, Rao Y, (2012) Synthesis of tri-and tetrasubstituted pyrazoles via Ru (II) catalysis: Intramolecular aerobic oxidative C-N coupling. Organic Letters 14:19, 5030-5033.
  • 9. Popiolek L, (2017) Hydrazide-hydrazones as potential antimicrobial agents: Overview of the literature since 2010. Medicinal Chemistry Research 26:2, 287-301.
  • 10. Rahmatzadeh SS, Karami B, Khodabakhshi S, (2015) A modified and practical synthetic route to indazoles and pyrazoles using tungstate sulfuric acid. Journal of the Chinese Chemical Society 62, 17-20.
  • 11. Anandarajagopal K, Sunilson JA, Illavarasu A, Thangavelpandian N, Kalijaran R, (2010) Antiepileptic and antimicrobial activities of novel 1-(unsubstituted/substituted)-3,5-dimethyl-1H-pyrazole derivatives. International Journal of ChemTech Research 281, 45-49.
  • 12. Parashar B, Jain A, Bharadwaj S, Sharma VK, (2012) Synthesis and pharmacological properties of some novel pyrazolidine and pyrazole derivatives. Medicinal Chemistry Research 21:8, 1692-1699.
  • 13. Breusch FL, Baykut F, (1953) Darstellung der Di-n-alkyl-ketone mit 15bis 22 C-Atomen (V.Mitteil. über isomere und homologe Reihen)Chemische Berichte 86, 684-688.
  • 14. Clinical and Laboratory Standards Institute, (1997) Reference Method for Broth Dilution Antifungal susceptibility testing of yeasts; Approved Standard- 2rd ed. M 27-A2; CLSI, Wayne, PA.
  • 15. Clinical and Laboratory Standards Institute, (2006) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 7th ed. Approved Standard M7-A7; CLSI, Wayne, PA.
Yıl 2019, Cilt: 6 Sayı: 2, 177 - 188, 15.06.2019
https://doi.org/10.18596/jotcsa.486487

Öz

Kaynakça

  • 1. Reddy KH, Reddy PS, Babu PR, (2000) Nuclease activity of 2-substituted heteroaromatic thiosemicarbazone and semicarbazone copper (II) complexes.Transition Metal Chemistry 25, 154-160.
  • 2. Babahan I, Coban EP, Biyik H, (2013) Synthesis, characterization and antimicrobial activities of vic-dioxime derivatives containing heteroaromatic hydrazine groups and their metal complexes.Maejo International Journal of Science and Technology 7:01, 26-41.
  • 3. Enyedy EA, Bognar GM, Nagy NV, Jakusch T, Kiss T, (2014) Solution speciation of potential anticancer metal complexes of salicylaldehyde semicarbazone and its bromo derivative.Polyhedron 67, 242-252.
  • 4. Kiasat AR, Kazemi F, Mehrjardi MF, (2007) Basic alumina as an efficient catalyst for preparation of semicarbazones in solvent free conditions. Journal of Chinese Chemical Society 54, 1337-1339.
  • 5. Sameem S, Kumar N, Pathak D, (2012) Synthesis and anticonvulsant activity of some newer semicarbazone derivatives. International Journal of Pharmaceutical Sciences and Drug Research 4:3, 195-198.
  • 6. Gup R, (2013), Synthesis and spectroscopic studies of new bis-acylhydrazone compounds. Chimica acta Turcica 35:1, 55-61.
  • 7. Torje IA, Valean AM, Cristea C, (2012) Phenothiazine-carboxaldehyde-hydrazone derivatives, synthesis, characterisation and electronic properties. Academia Romana 57:4-5, 337-344.
  • 8. Hu J, Chen S, Sun Y, Yang J, Rao Y, (2012) Synthesis of tri-and tetrasubstituted pyrazoles via Ru (II) catalysis: Intramolecular aerobic oxidative C-N coupling. Organic Letters 14:19, 5030-5033.
  • 9. Popiolek L, (2017) Hydrazide-hydrazones as potential antimicrobial agents: Overview of the literature since 2010. Medicinal Chemistry Research 26:2, 287-301.
  • 10. Rahmatzadeh SS, Karami B, Khodabakhshi S, (2015) A modified and practical synthetic route to indazoles and pyrazoles using tungstate sulfuric acid. Journal of the Chinese Chemical Society 62, 17-20.
  • 11. Anandarajagopal K, Sunilson JA, Illavarasu A, Thangavelpandian N, Kalijaran R, (2010) Antiepileptic and antimicrobial activities of novel 1-(unsubstituted/substituted)-3,5-dimethyl-1H-pyrazole derivatives. International Journal of ChemTech Research 281, 45-49.
  • 12. Parashar B, Jain A, Bharadwaj S, Sharma VK, (2012) Synthesis and pharmacological properties of some novel pyrazolidine and pyrazole derivatives. Medicinal Chemistry Research 21:8, 1692-1699.
  • 13. Breusch FL, Baykut F, (1953) Darstellung der Di-n-alkyl-ketone mit 15bis 22 C-Atomen (V.Mitteil. über isomere und homologe Reihen)Chemische Berichte 86, 684-688.
  • 14. Clinical and Laboratory Standards Institute, (1997) Reference Method for Broth Dilution Antifungal susceptibility testing of yeasts; Approved Standard- 2rd ed. M 27-A2; CLSI, Wayne, PA.
  • 15. Clinical and Laboratory Standards Institute, (2006) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 7th ed. Approved Standard M7-A7; CLSI, Wayne, PA.
Toplam 15 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Organik Kimya
Bölüm Makaleler
Yazarlar

Aysema Sayık Mehan Bu kişi benim 0000-0002-2516-850X

Ebru Senturk Bu kişi benim

Emel Mataracı Kara Bu kişi benim 0000-0003-4541-1893

Ayse Serguzel Yusufoglu 0000-0002-1437-3110

Yayımlanma Tarihi 15 Haziran 2019
Gönderilme Tarihi 21 Kasım 2018
Kabul Tarihi 5 Nisan 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 6 Sayı: 2

Kaynak Göster

Vancouver Sayık Mehan A, Senturk E, Mataracı Kara E, Yusufoglu AS. Synthesis, E/Z isomerisation and antimicrobial studies of different structured novel ketone derivatives. JOTCSA. 2019;6(2):177-88.