Synthesis and investigation of antimicrobial activities of nitrofurazone analogues containing hydrazide-hydrazone moiety

Popiołek, Łukasz; Biernasiuk, Anna

doi:10.1016/j.jsps.2017.05.006

Cited by 47 publications

(34 citation statements)

References 34 publications

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“…In our previous research, a series of hydrazide‐hydrazones showed very promising antimicrobial and antifungal activities (Popiołek & Biernasiuk, , , , ; Popiołek, Biernasiuk, et al, ). For instance, a series of nitrofurazone analogues containing hydrazide‐hydrazone moiety synthesized by our group displayed, depending on the compounds and bacterial or fungal strains, higher antimicrobial activity than ciprofloxacin, nitrofurantoin or cefuroxime, which were used as reference substances (Popiołek & Biernasiuk, ). In that research, we used different hydrazides of carboxylic acids and condensed them with 5‐nitro‐2‐furaldehyde (Popiołek & Biernasiuk, ).…”

Section: Introductionmentioning

confidence: 98%

Synthesis of promising antimicrobial agents: hydrazide‐hydrazones of 5‐nitrofuran‐2‐carboxylic acid

et al. 2019

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In this research, we synthesized and evaluated for in vitro antimicrobial activity a new series of hydrazide-hydrazones obtained from 5-nitrofuran-2-carboxylic acid.New compounds were identified and characterized by spectral methods ( 1 H NMR and 13 C NMR). All tested hydrazide-hydrazones proved to be promising antimicrobial agents. Antimicrobial activity and antifungal activity of new derivatives of 5-nitrofuran-2-carboxylic acid were revealed in many cases to be higher than the activity of reference substances (nitrofurantoin, cefuroxime and ampicillin). Yield: 47%; M.p.: 126°C; 1 H NMR (DMSO-d 6 ) δ (ppm): 2.09 (s, 3H, CH 3 ), 2.57-2.61 (t, 2H, CH 2 , J = 6 Hz), 2.68-2.74 (q, 2H, CH 2 , J = 6 Hz), 7.50-7.51 (d, 1H, ArH, J = 3 Hz), 7.78-7.79 (d, 1H, ArH, J = 3 Hz), 7.79-7.83 (t, 1H, =CH, J = 9 Hz, J = 3 Hz), 11.95 (s, 1H, NH); 13 C NMR (DMSO-d 6 ) δ (ppm): 14.6 (SCH 3 ), 30.3 (CH 2 ), 33.6 (CH 2 ), 115.4, 123.6, 138.2, 150.1 (4C ar ), 154.8 (=CH), 156.2 (C = O); For 262 | POPIOŁEK Et al.

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Section: Introductionmentioning

confidence: 98%

Synthesis of promising antimicrobial agents: hydrazide‐hydrazones of 5‐nitrofuran‐2‐carboxylic acid

et al. 2019

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“…[45] Iproniazide, an isoniazid derivative, originally used as an antituberculosis medicine, showed mood elevation in depressed patients, which makes it the first MAO (monoamine oxidase) inhibitor. [46] Due to the broad spectrum of biological activity, especially antimicrobial activity of isonicotinic acid [44,45] and 1,3,4-oxadiazole derivatives, [10 -15] as well as that of hydrazide-hydrazones, reported by our group earlier, [47][48][49][50][51][52] we decided to combine these two pharmacophores in one chemical structure with the hope of obtaining interesting antimicrobial agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis andin VitroAntimicrobial Activity Screening of New 3‐Acetyl‐2,5‐disubstituted‐1,3,4‐oxadiazoline Derivatives

Popiołek

Biernasiuk

Paruch

et al. 2019

Chemistry & Biodiversity

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Thirteen new 3‐acetyl‐2,5‐disubstituted‐1,3,4‐oxadiazoline derivatives were synthesized from corresponding hydrazide‐hydrazones of isonicotinic acid in the reaction with acetic anhydride. The obtained compounds were identified with the use of spectral methods (IR, 1H‐NMR, 13C‐NMR, MS). In vitro antimicrobial activity screening of synthesized compounds against a panel of bacteria and fungi revealed interesting antibacterial and antifungal activity of tested 1,3,4‐oxadiazoline derivatives, which is comparable to that of commonly used antimicrobial agents.

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“…As well as other NSAIDs, naproxen was reported to be efficient in the prevention of many cancers [3][4][5]. Hydrazide-hydrazones [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] and 1,2,4-triazole rings [22][23][24][25][26] have diverse biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

Han¹,

Bekçi²,

Cumaoğlu³

et al. 2018

jrp

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How to cite this article: Han M, Bekçi H, Cumaoğlu A, Küçükgüzel ŞG. Synthesis and characterization of 1,2,4-triazole containing hydrazidehydrazones derived from (S)-Naproxen as anticancer agents. Marmara Pharm J. 2018; 22 (4): 559-569. ABSTRACT: A novel series of new naproxen derivativeswere synthesized, in this study. The structures of compounds 5, 6 and 7a-m were defined by spectral ( 1 H-NMR, 13 C-NMR, HR-MS and FT-IR) methods and their purity was proven by elemental analysis, thin layer chromatography and high pressure liquid chromatography. These compounds were evaluated for in vitro anticancer activity by using MTS method against PC-3 and DU-143 (androgen-independent human prostate cancer cell lines) and LNCaP (androgen-sensitive human prostate adenocarcinoma) prostate cancer cell lines. Cisplatin was used as the positive sensitivity reference standard. Compounds (7a-m) exhibited anticancer activity with IC50 values of 87.2-400 µM against prostate cancer cell lines.

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Synthesis and investigation of antimicrobial activities of nitrofurazone analogues containing hydrazide-hydrazone moiety

Cited by 47 publications

References 34 publications

Synthesis of promising antimicrobial agents: hydrazide‐hydrazones of 5‐nitrofuran‐2‐carboxylic acid

Synthesis of promising antimicrobial agents: hydrazide‐hydrazones of 5‐nitrofuran‐2‐carboxylic acid

Synthesis andin VitroAntimicrobial Activity Screening of New 3‐Acetyl‐2,5‐disubstituted‐1,3,4‐oxadiazoline Derivatives

Synthesis and characterization of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen as anticancer agents

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