Diazinium salts with dihydroxyacetophenone skeleton: Syntheses and antimicrobial activity

Bălan, Ana Maria; Florea, Ondina; Moldoveanu, Costel; Zbancioc, Gheorghiță; Iurea, Dorina; Mangalagiu, Ionel I.

doi:10.1016/j.ejmech.2008.06.017

Cited by 31 publications

(21 citation statements)

References 11 publications

(2 reference statements)

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“…Recently, we reported successful results on the identification of new antimicrobial (type I) [12][13][14] and anticancer (type II) [9,21] compounds, which contain a diazine or an acetophenone skeleton as pharmacophoric moiety. As a consequence, in an attempt to increase the potential of pharmacophoric models, we decided to combine their respective biological potentials.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and In vitro Analysis of Novel Dihydroxyacetophenone Derivatives with Antimicrobial and Antitumor Activities

Zbancioc¹,

Tuchiluş²,

Rotinberg³

et al. 2014

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Herein we report a feasible study concerning the design, syntheses and in vitro antimicrobial and antitumoral activities of some novel compounds with dihydroxyacetophenone (DA) moiety. An efficient and general method for the preparation of diazine with dihydroxyacetophenone (DDA) skeleton under conventional thermal heating (TH), microwave (MW) and ultrasounds (US) irradiation is presented. Antimicrobial and antitumoral tests prove that some dihydroxyacetophenone compounds (the brominated derivatives BrDA 3) have a significant biological activity. It is also to be pointed out that, basically all the dihydroxyacetophenone derivatives proved to have a powerful antibacterial activity against drug resistant Gram-negative strain Pseudomonas aeruginosa ATCC 27853. Of particular interest could be the excellent antibacterial activity of our dihydroxyacetophenone compounds against drug resistant Gram-negative strain Pseudomonas aeruginosa.

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Section: Resultsmentioning

confidence: 99%

“…Synthesis of functionalized acetophenone derivatives is an important goal for organic synthesis, these derivatives and particulary dihydroxyacetophenone, exhibiting interesting biological properties, these including antimicrobial [14] and anticancer activities [15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In vitro Analysis of Novel Dihydroxyacetophenone Derivatives with Antimicrobial and Antitumor Activities

Zbancioc¹,

Tuchiluş²,

Rotinberg³

et al. 2014

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“…riparia . Taking into account the antimicrobial properties of acetophenone derivatives, the occurrence of these precursors in GTs strongly suggests their functional roles against biotic stress. Present results would also indicate that, at least in part, the synthesis of benzofurans and acetophenone derivatives in F .…”

Section: Resultsmentioning

confidence: 99%

Volatiles and Nonvolatiles in Flourensia campestris Griseb. (Asteraceae), How Much Do Capitate Glandular Trichomes Matter?

Piazza

López

Silva

et al. 2018

Chemistry & Biodiversity

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The distribution and ultrastructure of capitate glandular trichomes (GTs) in Flourensia species (Asteraceae) have been recently elucidated, but their metabolic activity and potential biological function remain unexplored. Selective nonvolatile metabolites from isolated GTs were strikingly similar to those found on leaf surfaces. The phytotoxic allelochemical sesquiterpene (-)-hamanasic acid A ((-)-HAA) was the major constituent (ca. 40%) in GTs. Although GTs are quaternary ammonium compounds (QACs)-accumulating species, glycine betaine was not found in GTs; it was only present in the leaf mesophyll. Two (-)-HAA accompanying surface secreted products: compounds 4-hydroxyacetophenone (piceol; 1) and 2-hydroxy-5-methoxyacetophenone (2), which were isolated and fully characterized (GC/MS, NMR), were present in the volatiles found in GTs. The essential oils of fresh leaves revealed ca. 33% monoterpenes, 26% hydrocarbon- and 30% oxygenated sesquiterpenes, most of them related to cadinene and bisabolene derivatives. Present results suggest a main role of GTs in determining the volatile and nonvolatile composition of F. campestris leaves. Based on the known activities of the compounds identified, it can be suggested that GTs in F. campestris would play key ecological functions in plant-pathogen and plant-plant interactions. In addition, the strikingly high contribution of compounds derived from cadinene and bisabolene pathways, highlights the potential of this species as a source of high-valued bioproducts.

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“…[1][2][3][4][5][6][7][8][9][10] It was previous described in the literature that 6-membered ring nitrogen heterocycles possess a large variety of applications in very different fields, such us medicinal chemistry (antibacterial and antifungal, antituberculosis, anticancer, etc. ), [11][12][13][14][15][16][17][18][19][20] opto-electronics (highly fluorescent derivatives, compounds with liquid crystal and ionic liquids properties and semiconductors) [21][22][23][24][25][26][27] and agriculture (herbicidal activity and grow up factor for plants). 28 To continue our research in the field of 1,2 diazines, the structure of 6,6'-(Oxybis(4,1-phenylene))bis-(2-allylpyridazin-3(2H)-one) was investigated by NMR and X-ray studies.…”

Section: Introductionmentioning

confidence: 99%

NMR and X-ray Studies Concerning Structure of 6,6’-(Oxybis(4,1-phenylene))bis-(2-allylpyridazin- 3(2H)-one)

et al. 2014

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The structural NMR and X-ray studies of 6,6'-(Oxybis(4,1-phenylene))bis-(2-allylpyridazin-3(2H)-one), a bis-pyridazine derivative heterocycle, are reported in this study. Both 1 H-and 13 C-NMR confirm the proposed structure of compound. In order to establish unequivocally the structure of compound, the X-ray data analysis was performed. The compound crystallizes in the triclinic P-1(2) space group with a = 10.3699(7) Å, b = 10.6972(6) Å, c = 11.0449(4) Å, α = 87.941(5)°, β = 75.564(5)°, γ = 72.055(5)°, V= 1127.68 (12) Å 3 and Z = 2. Molecular and crystal packing parameters for the novel heterocyclic system were obtained from intensity data collected at room temperature. The two phenyl rings (from the diphenyl ether moiety) are perpendicular one to each other and, on its turn, each phenyl ring is almost coplanar with the pyridazine ring.

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Diazinium salts with dihydroxyacetophenone skeleton: Syntheses and antimicrobial activity

Cited by 31 publications

References 11 publications

Synthesis and In vitro Analysis of Novel Dihydroxyacetophenone Derivatives with Antimicrobial and Antitumor Activities

Synthesis and In vitro Analysis of Novel Dihydroxyacetophenone Derivatives with Antimicrobial and Antitumor Activities

Volatiles and Nonvolatiles in Flourensia campestris Griseb. (Asteraceae), How Much Do Capitate Glandular Trichomes Matter?

NMR and X-ray Studies Concerning Structure of 6,6’-(Oxybis(4,1-phenylene))bis-(2-allylpyridazin- 3(2H)-one)

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