Synthesis and in vitro antimicrobial activity of new steroidal hydrazone derivatives

Mistry, Shailesh; Singh, Akhilesh Kumar

doi:10.1186/s43094-021-00391-4

Cited by 8 publications

(6 citation statements)

References 36 publications

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“…Hydrazide/hydrazone derivatives contain an azomethine moiety (−NHN=CH−) linked with the carbonyl group, were found to be involved in different biological activities viz . antitubercular, [59] anticancer, [60] antioxidant, [61] and antimicrobial, etc [62] . Nitrofurazone, furazolidone, nitrofurantoin, isoniazid etc ., are pharmacologically active antibacterial drugs that contain hydrazide/hydrazone moiety (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

“…antitubercular, [59] anticancer, [60] antioxidant, [61] and antimicrobial, etc. [62] Nitrofurazone, furazolidone, nitrofurantoin, isoniazid etc., are pharmacologically active antibacterial drugs that contain hydrazide/hydrazone moiety (Figure 2). [63,64] Amongst various reported activities, the antibacterial activity of quinoline hydrazide/hydrazone derivatives is noteworthy.…”

Section: Introductionmentioning

confidence: 99%

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Quinoline Hydrazide/Hydrazone Derivatives: Recent Insights on Antibacterial Activity and Mechanism of Action

et al. 2023

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Antibiotics are becoming gradually ineffective due to drug resistance, leading to greater difficulty in the treatment of infectious diseases. Therefore, the development of new chemical entities with different mechanisms of action is essential in the fight against resistant microorganisms. Various studies have shown that quinoline hydrazide/hydrazone derivatives possess several biological activities, such as antimalarial, antitubercular, anticancer, anti-inflammatory, and antimicrobial. Among these activities, the antibacterial activity of quinoline hydrazide/ hydrazone derivatives is noteworthy. The synthetic flexibility of the quinoline ring has led to the development of a wide range of structurally diverse quinoline hydrazide/hydrazone derivatives, which can act at various bacterial targets such as DNA gyrase, glucosamine-6-phosphate synthase, enoyl ACP reductase, and 3-ketoacyl ACP reductase. This review emphasizes the antibacterial potential of various reported quinoline hydrazide/ hydrazone derivatives based on substitution in the quinoline ring. The antibacterial activity of various metal-quinoline hydrazide/hydrazone complexes is also discussed. The aim of this review is to assemble and scrutinize the latest reports in this promising area of drug development.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Quinoline Hydrazide/Hydrazone Derivatives: Recent Insights on Antibacterial Activity and Mechanism of Action

et al. 2023

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“…Nowadays, a number of steroidal hydrazone derivatives have been developed and evaluated for their antimicrobial activity [ 19 , 20 , 21 , 22 , 23 , 24 ]. Among these hydrazones are some 5α-steroidal derivatives of the androstane and pregnane series with different functional groups.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity of Some Steroidal Hydrazones

et al. 2023

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Twelve steroid based hydrazones were in silico evaluated using computer program PASS as antimicrobial agents. The experimental evaluation revealed that all compounds have low to moderate antibacterial activity against all bacteria tested, except for B.cereus with MIC at a range of 0.37–3.00 mg/mL and MBC at 0.75–6.00 mg/mL. The most potent appeared to be compound 11 with MIC/MBC of0.75/1.5 mg/mL, respectively. The evaluation of antibacterial activity against three resistant strains MRSA, E.coli and P.aeruginosa demonstrated superior activity of compounds against MRSA compared with ampicillin, which did not show bacteriostatic or bactericidal activities. All compounds exhibited good antifungal activity with MIC of 0.37–1.50 mg/mL and MFC of 1.50–3.00 mg/mL, but with different sensitivity against fungi tested. According to docking studies, 14-alpha demethylase inhibition may be responsible for antifungal activity. Two compounds were evaluated for their antibiofilm activity. Finally, drug-likeness and docking prediction were performed.

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“…Numerous studies have demonstrated the potent antimicrobial activity of hydrazone-based compounds against various bacterial and fungal pathogens. [8][9][10][11][12] Additionally, hydrazone derivatives have represented promising anticancer activity by inhibiting cancer cell proliferation and inducing apoptosis. [13][14][15][16][17][18][19] The mechanism of action of these compounds involves targeting specific cellular pathways and enzymes, facilitated by their multiple hydrogen bond acceptor/donor atoms that can interact with biological targets.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Novel Metacetamol Derivatives with Hydrazone Moiety as Anticancer and Antimicrobial Agents

Şenkardeş,

Atlıhan,

Çayır

et al. 2023

Chemistry & Biodiversity

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By exploiting the wide biological potential of the hydrazone scaffold, a series of hydrazone derivatives were synthesized, starting from N‐(3‐hydroxyphenyl)acetamide (metacetamol). The structures of the compounds were determined using IR, 1H and 13C‐NMR, and mass spectroscopic methods. The obtained molecules (3 a–j) were evaluated for their anticancer potential against MDA‐MB‐231 and MCF‐7 breast cancer cell lines. According to the CCK‐8 assay, all tested compounds showed moderate to potent anticancer activity. Among them, N‐(3‐(2‐(2‐(4‐nitrobenzylidene)hydrazinyl)‐2‐oxoethoxy)phenyl)acetamide (3 e) was found to be the most effective derivative with an IC50 value of 9.89 μM against MDA‐MB‐231 cell lines. This compound was further tested for its potential effects on the apoptotic pathway. Molecular docking studies was also carried out for 3 e in the colchicine binding pocket of tubulin. Additionally, compound 3 e also demonstrated effective antifungal activity, particularly against Candida krusei (MIC=8 μg/ml), indicating that nitro group at the 4th position of the phenyl ring was the most preferable substituent for both cytotoxic and antimicrobial activity. Our preliminary findings suggest that compound 3 e could be exploited as a leading structure for further anticancer and antifungal drug development.

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Synthesis and in vitro antimicrobial activity of new steroidal hydrazone derivatives

Cited by 8 publications

References 36 publications

Quinoline Hydrazide/Hydrazone Derivatives: Recent Insights on Antibacterial Activity and Mechanism of Action

Quinoline Hydrazide/Hydrazone Derivatives: Recent Insights on Antibacterial Activity and Mechanism of Action

Antimicrobial Activity of Some Steroidal Hydrazones

Synthesis and Evaluation of Novel Metacetamol Derivatives with Hydrazone Moiety as Anticancer and Antimicrobial Agents

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