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

Zbancioc, Ana Maria; Tuchiluş, Cristina; Rotinberg, Pincu; Mihai, Cosmin Teodor; Mangalagiu, Ionel I.; Zbancioc, Gheorghiță

doi:10.2174/15734064113096660070

Cited by 19 publications

(14 citation statements)

References 22 publications

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“…Encouraged by our recent results in the field of (di)azine with antimicrobial activity [ 11 , 15 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ], we report here the design, synthesis, antibacterial and antifungal evaluation of some newly hybrid quinoline-sulfonamide complexes.…”

Section: Introductionmentioning

confidence: 99%

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

et al. 2020

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Two new series of hybrid quinoline-sulfonamide complexes (M2+: Zn2+, Cu2+, Co2+ and Cd2+) derivatives (QSC) were designed, synthesized and tested for their antimicrobial activity. The synthesis is straightforward and efficient, involving two steps: acylation of aminoquinoline followed by complexation with metal acetate (Cu2+, Co2+ and Cd2+) or chloride (Zn2+). The synthesized QSC compounds were characterized by FTIR and NMR spectroscopy and by X-ray diffraction on single crystal. The QSC compounds were preliminary screened for their antibacterial and antifungal activity and the obtained results are very promising. In this respect, the hybrid N-(quinolin-8-yl)-4-chloro-benzenesulfonamide cadmium (II), considered as leading structure for further studies, has an excellent antibacterial activity against Staphylococcus aureus ATCC25923 (with a diameters of inhibition zones of 21 mm and a minimum inhibitory concentration (MIC) of 19.04 × 10−5 mg/mL), a very good antibacterial activity against Escherichia coli ATCC25922 (with a diameters of inhibition zones of 19 mm and a MIC of 609 × 10−5 mg/mL), and again an excellent antifungal activity against Candida albicans ATCC10231 (with a diameters of inhibition zones of 25 mm and a MIC of 19.04 × 10−5 mg/mL).

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Section: Introductionmentioning

confidence: 99%

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

et al. 2020

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“…Overall, the use of US proved to be more efficient than MW or TH. The in vitro anticancer assay proves that some of the obtained compounds have a significant antitumor activity and a moderate antifungal activity, while the antibacterial activity is negligible [ 34 ].…”

Section: Resultsmentioning

confidence: 99%

[3 + n] Cycloaddition Reactions: A Milestone Approach for Elaborating Pyridazine of Potential Interest in Medicinal Chemistry and Optoelectronics

Mantu

Mangalagiu

2021

Molecules

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During the last few decades, pyridazine derivatives have emerged as privileged structures in heterocyclic chemistry, both because of their excellent chemistry and because of their potential applications in medicinal chemistry and optoelectronics. This review is focused on the recent advances in [3 + n] cycloaddition reactions in the pyridazine series as well as their medicinal chemistry and optoelectronic applications over the last ten years. The stereochemistry and regiochemistry of the cycloaddition reactions are discussed. Applications in optoelectronics (in particular, as fluorescent materials and sensors) and medicinal chemistry (in particular, antimicrobials and anticancer) are also reviewed.

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“…In previous research work, we studied the synthesis under conventional thermal heating and under US or MW irradiation of a series of new pyridazinium/phthalazinium derivatives with a dihydroxyacetophenone skeleton as well as their antimicrobial and/or anticancer activity [ 32 , 34 , 38 ]. Considering the good results obtained, we decided to broaden these studies to the pyrrolophthalazine derivatives with a dihydroxyacetophenone skeleton.…”

Section: Resultsmentioning

confidence: 99%

Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes

et al. 2020

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We present herein a straightforward and efficient pathway for the synthesis of pyrrolophthalazine cycloadducts via Huisgen [3 + 2] dipolar cycloaddition reactions of phthalazinium ylides to methyl propiolate or dimethyl acetylenedicarboxylate (DMAD). A thoroughly comparative study concerning the efficiency of synthesis, conventional thermal heating (TH) versus microwave (MW) and ultrasound (US) irradiation, has been performed. The cycloaddition reactions of phthalazinium ylides to methyl propiolate occur regiospecific, with a single regioisomer being obtained. Under conventional TH, the cycloaddition reaction of phthalazinium ylides with DMAD occurs to a mixture of inseparable partial and fully aromatized pyrrolophthalazine cycloadducts, while MW or US irradiation are leading only to fully aromatized compounds, with the reactions becoming selective. A feasible mechanism for formation of fully aromatized compounds is presented. Besides selectivity, it has to be noticed that the reaction setup under MW or US irradiation offer a number of other certain advantages: higher yields, decreasing of the amount of used solvent comparative with TH, decreasing of the reaction time from hours to minutes and decreasing of the consumed energy; consequently, these reactions could be considered environmentally friendly.

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

Cited by 19 publications

References 22 publications

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

Hybrid Quinoline-Sulfonamide Complexes (M2+) Derivatives with Antimicrobial Activity

[3 + n] Cycloaddition Reactions: A Milestone Approach for Elaborating Pyridazine of Potential Interest in Medicinal Chemistry and Optoelectronics

Huisgen [3 + 2] Dipolar Cycloadditions of Phthalazinium Ylides to Activated Symmetric and Non-Symmetric Alkynes

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