Design and drug-like properties of new 5-methoxysalicylaldehyde based hydrazones with anti-breast cancer activity

Nikolova-Mladenova, Boryana; Momekov, Georgi; Ivanov, D.; Bakalova, Adriana

doi:10.1016/j.jab.2017.04.004

Cited by 15 publications

(20 citation statements)

References 25 publications

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“…A significant part among thousands of new biologically active compounds synthesized each year by medicinal chemists around the world belongs to the group of hydrazide‐hydrazones (Bala, Uppal, Kajal, Kamboj, & Sharma, ; Popiołek, ; Rollas & Küçükgüzel, ). This is due to the fact that this group of compounds possesses very interesting and broad spectrum of biological properties (Bala et al, ; Popiołek, ; Rollas & Küçükgüzel, ), which include antimicrobial (Backes, Neumann, & Jursic, ; Manikandan et al, ; Metwally, Abdel‐Aziz, Lashine, Husseiny, & Badawy, ; Rollas, Gulerman, & Erdeniz, ; Zha et al, ), anticancer (Kumar, Kumar, Ghosh, & Shah, ; Nasr et al, ; Nasr, Bondock, & Youns, ; Nikolova‐Mladenova, Momekov, Ivanov, & Bakalova, ; Sreenivasulu, Reddy, Sujitha, Kumar, & Raju, ; Tantak et al, ), anti‐inflammatory (Gökçe, Utku, & Küpeli, ; Moldovan et al, ; Sondhi, Dinodia, & Kumar, ), anticonvulsant (Dehestani et al, ) and analgesic activity (Navidpour, Shafaroodi, Saeedi‐Motahar, & Shafiee, ).…”

Section: Introductionmentioning

confidence: 99%

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: 99%

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

et al. 2019

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“…Hydrazide-hydrazones and benzenesulphonohydrazones exhibit anticancer activity (11,12,(38)(39)(40)(41)(42). Numerous studies have confirmed that these molecules displayed significant antiproliferative activity against the following cancer cell lines: Leukaemia (HL-60, SKW-3 and BV-173), lung (A549), liver (HepG2), renal (769-P), ovarian (SK-OV-3), breast (MDA-MB-231 and MCF-7), cervical (HeLa), skin (SK-MEL-2), colon (HCT15), gastric (Bc G-823) and pancreatic (MIA-PaCa-2) cancer (37,(43)(44)(45)(46)(47). The present study was a pilot study focused on the synthesis, lipophilicity and screening of the antiproliferative potential of newly developed benzenesulphonohydrazones.…”

Section: Discussionmentioning

confidence: 99%

“…However, both ortho-and meta-methoxy groups at the phenyl ring of compound 5 provided a strong cytotoxic effect, but they also exerted this effect on normal cells. Nikolova-Mladenova et al (46) have reported the significance of the methoxy substituent at the phenyl ring of hydrazide-hydrazone derivatives for its cytotoxicity. In addition, the aforementioned study and another study (24) have reported that the hydroxy groups are responsible for the increase in cytotoxic potential towards cancer cells.…”

Section: Discussionmentioning

confidence: 99%

New benzenesulphonohydrazide derivatives as potential antitumour agents

et al. 2020

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Cancer treatment remains a serious challenge worldwide. Thus, finding novel antitumour agents is of great importance. In the present study, nine new benzenesulphonohydrazide derivatives (1-9) were synthesized, and the chemical structures of the obtained compounds were confirmed by spectral analysis methods, including IR, 1 H nuclear magnetic resonance (NMR) and 13 C NMR. Experimental lipophilicity values were established using reversed phase-high performance thin layer chromatography. The antiproliferative activity of the synthesized compounds was tested against three tumour cell lines (769-P, HepG2 and NCI-H2170) and one normal cell line (Vero). Among the newly developed molecules, compound 4 exhibited generally the highest cytotoxicity across all tumour cell lines, and it was highly selective. However, higher selectivity towards the tested cancer cell lines was observed using compound 2, when compared with compound 4, which also exhibited significant antiproliferative activity against these tumour cells. In 769-P cells, compounds 5 and 6 were the most selective among all tested compounds. Compound 5 exhibited high cytotoxicity with an estimated IC 50 value of 1.94 µM. In the NCI-H2170 cell line, compound 7 was the most cytotoxic and the most selective. In brief, the combination of fluorine and bromine substituents at the phenyl ring showed the most promising results, exerting high cytotoxicity and selectivity towards cancer cells. The renal adenocarcinoma cell line (769-P) appeared to be the most sensitive to the anticancer properties of the novel benzenesulphonohydrazones.

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“…Hydrazone derivatives are considered among the most important molecules in organic chemistry, which show an efficient activity in a wide range of applications including development of new drugs with anti-cancer [1] , [2] , [3] , [4] , antimicrobial [5] , [6] , [7] , analgesic [8] , antihypertensive [9] , anticonvulsant [10] , anti-inflammatory [11] , antituberculosis [ 12 , 13 ], antitumoral [ 14 , 15 ], anti-HIV [ 16 , 17 ], antimalarial [18] , antidepressant [19] , vasodilatory [20] , anti-Alzheimer [ 21 , 22 ], and anti-corrosion activities [ 23 , 24 ]. The presence of both N – N and C=N functional groups in the structure of hydrazones is responsible of their high therapeutic activity [25] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, DFT, antioxidant, antibacterial, pharmacokinetics and inhibition of SARS-CoV-2 main protease of some heterocyclic hydrazones

Adjissi

Chafai

Benbouguerra

et al. 2022

Journal of Molecular Structure

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Design and drug-like properties of new 5-methoxysalicylaldehyde based hydrazones with anti-breast cancer activity

Cited by 15 publications

References 25 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

New benzenesulphonohydrazide derivatives as potential antitumour agents

Synthesis, characterization, DFT, antioxidant, antibacterial, pharmacokinetics and inhibition of SARS-CoV-2 main protease of some heterocyclic hydrazones

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