Synthesis, in vitro biological evaluation and in silico molecular docking studies of novel β-lactam-anthraquinone hybrids

Mohamadzadeh, Masoud; Zarei, Maaroof; Vessal, Mahmood

doi:10.1016/j.bioorg.2019.103515

Cited by 28 publications

(17 citation statements)

References 48 publications

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“…The β-lactam derivatives are promising candidates in the progress of tubulin-targeting agents for the treatment of colon and breast cancers. A series of β-lactam-anthraquinone hybrids 3 were manufactured as potential antibacterial and antifungal agents [52]. Among them, the thio-methyl substituent at C-3 and the 3,4,5-trimethoxy phenyl group at the C-4 position of the β-lactam ring scaffold (compound 3a) exhibited the most potent antibacterial activity (MIC = 0.25 g/mL) against the Staphylococcus aureus bacterial strain, compared with the standard ciprofloxacin (MIC = 0.5 g/mL) ( Figure 5).…”

Section: β-Lactamsmentioning

confidence: 99%

“…Furthermore, the active hybrid was evaluated by molecular docking studies and the carbonyl groups of the anthraquinone moiety and the β-lactam ring had three hydrogen bonding interactions with Lys273, Asp295 and Val277 residuces, while the MeS group interacted with the active site of Tyr272 and the 3,4,5-trimethoxyphenyl group exerted hydrophobic interactions with His293, Lys289, Gln292 and Lys319 residues of a penicillin-binding protein (PBP). A series of β-lactam-anthraquinone hybrids 3 were manufactured as potential antibacterial and antifungal agents [52]. Among them, the thio-methyl substituent at C-3 and the 3,4,5-trimethoxy phenyl group at the C-4 position of the β-lactam ring scaffold (compound 3a) exhibited the most potent antibacterial activity (MIC = 0.25 g/mL) against the Staphylococcus aureus bacterial strain, compared with the standard ciprofloxacin (MIC = 0.5 g/mL) ( Figure 5).…”

Section: β-Lactamsmentioning

confidence: 99%

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A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

et al. 2020

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The analogs of nitrogen-based heterocycles occupy an exclusive position as a valuable source of therapeutic agents in medicinal chemistry. More than 75% of drugs approved by the FDA and currently available in the market are nitrogen-containing heterocyclic moieties. In the forthcoming decade, a much greater share of new nitrogen-based pharmaceuticals is anticipated. Many new nitrogen-based heterocycles have been designed. The number of novel N-heterocyclic moieties with significant physiological properties and promising applications in medicinal chemistry is ever-growing. In this review, we consolidate the recent advances on novel nitrogen-containing heterocycles and their distinct biological activities, reported over the past one year (2019 to early 2020). This review highlights the trends in the use of nitrogen-based moieties in drug design and the development of different potent and competent candidates against various diseases.

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Section: β-Lactamsmentioning

confidence: 99%

Section: β-Lactamsmentioning

confidence: 99%

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

et al. 2020

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“…and Aspergillus spp. (Gowri et al 2016 ; O'Driscoll et al 2008 ; Mohamadzadeh et al 2020 ). However, studies have indicated that β-lactam antibiotics are unable to inhibit the growth of Candida species, and amoxicillin can increase the virulence of Candida krusei and Candida tropicalis in Caenorhabditis elegans (Aguiar Cordeiro et al 2018 ).…”

Section: Antibacterial Drugsmentioning

confidence: 99%

Drug repurposing strategies in the development of potential antifungal agents

Zhang

Liu

Zeng

et al. 2021

Appl Microbiol Biotechnol

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The morbidity and mortality caused by invasive fungal infections are increasing across the globe due to developments in transplant surgery, the use of immunosuppressive agents, and the emergence of drug-resistant fungal strains, which has led to a challenge in terms of treatment due to the limitations of three classes of drugs. Hence, it is imperative to establish effective strategies to identify and design new antifungal drugs. Drug repurposing is a potential way of expanding the application of existing drugs. Recently, various existing drugs have been shown to be useful in the prevention and treatment of invasive fungi. In this review, we summarize the currently used antifungal agents. In addition, the most up-to-date information on the effectiveness of existing drugs with antifungal activity is discussed. Moreover, the antifungal mechanisms of existing drugs are highlighted. These data will provide valuable knowledge to stimulate further investigation and clinical application in this field. Key points • Conventional antifungal agents have limitations due to the occurrence of drug-resistant strains. • Non-antifungal drugs act as antifungal agents in various ways toward different targets. • Non-antifungal drugs with antifungal activity are demonstrated as effective antifungal strategies.

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“…β-Lactams are another highly unique class of heterocyclic compounds possessing diverse biological applications as anti-HIV, [32] antimalarial, [33] antimicrobial, [34][35][36][37] antioxidant, [38,39] antiinflammation, [40,41] and anticancer activities. [40,42,43] β-Lactam is the core component of naturally compounds such as penicillins, cephalosporins, clavams, carbapenems and the monocyclic β-lactams, which are produced by a wide range of organisms.…”

Section: Introductionmentioning

confidence: 99%

Sulfonamide‐β‐lactam Hybrids Incorporating the Piperazine Moiety as Potential Antiinflammatory Agent with Promising Antibacterial Activity

et al. 2021

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Several monocyclic β-lactams have been synthesized via a [2 + 2] ketene-imine cycloaddition reaction (Staudinger reaction) and evaluated for their biological activities. The structure of synthesized products was confirmed by spectral data and elemental analyses. β-Lactams 4 b and 4 h exhibited 31 and 27 anti-inflammatory ratios, respectively, which are as well as the well-known dexamethasone corticosteroid with a 32 antiinflammatory ratio. The two most active compounds 4 b and 4 h showed IC 50 values more than 200 μM against the HepG2 cell line, in comparison with doxorubicin (IC 50 < 1 μM), indicated biocompatibility and nontoxic behavior. 4 d, 4 j, 4 k, and 4 l, were active against S. aureus and E. coli and had broad spectrum property. The tested compounds were subjected to in silico prediction of pharmacokinetics properties (ADMET) to assess the potential in vivo effectiveness. The molecular docking study confirmed that the active inhibitors 4 b and 4 h are well fitted in the iNOS active site. This data suggests that 4 b and 4 h could potentially serve as effective iNOS inhibitors, a represent promising lead compounds for treating inflammatory disorders.

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Synthesis, in vitro biological evaluation and in silico molecular docking studies of novel β-lactam-anthraquinone hybrids

Cited by 28 publications

References 48 publications

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

Drug repurposing strategies in the development of potential antifungal agents

Sulfonamide‐β‐lactam Hybrids Incorporating the Piperazine Moiety as Potential Antiinflammatory Agent with Promising Antibacterial Activity

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