Synthesis, Antimicrobial Capability and Molecular Docking of Heterocyclic Scaffolds Clubbed by 2-Azetidinone, Thiazole and Quinoline Derivatives

Desai, N. C.; Harsora, J P; Monapara, Jahnvi D.; Khedkar, Vijay M.

doi:10.1080/10406638.2021.1877747

Cited by 14 publications

(30 citation statements)

References 45 publications

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“…Thiazo-and selenazolidine-4-ones are an important class of compounds in organic and medicinal chemistry [16][17]. The 4-thiazolidinone or 4selenazolidinone ring system is a core structure in various synthetic pharmaceutical agents, displaying a broad spectrum of biological activities such as antitubercular, antibacterial, anti-inflammatory, antioxidant agents, antiviral agents, especially as anti-HIV agents, and their use as anticancer drugs [13,[18][19][20]. They received considerable attention during the last two decades as they are gifted with a variety of activities and have a wide range of therapeutic properties [16][17].…”

Section: Sulfonamidesmentioning

confidence: 99%

Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

2022

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A new series of azetidinone (Z2a-Z2e, Z2g), thiazolidinone and selenazolidinone derivatives (Z2B, Z2E, Z2B', Z2E') based on sulfonamide have been synthesized and characterized by different instrumental techniques, such as elemental analyses, FTIR, multinuclear NMR (1H, 13C) and mass spectrometry. The tested compound containing selenium (Z2E') was less toxic than its analogs containing sulfur (Z2E) based on the LD50 value determined by Dixon's up and down method. All compounds showed antibacterial properties, however, Z2E' was more active against Gram-negative bacteria: Escherichia coli and Pseudomonas aeruginosa than Gram-positive ones: Streptococcus aureus and Bacillus, with the lowest MIC value of 5 mg/mL. All compounds showed good antioxidant activity at a lower rate than the standard compound BHT (82%). More precisely, Z2b was the main compound that possess strong activity as an antioxidant (73%). MTT viability assay showed that all tested compounds had cytotoxic effects on MCF-7 cells after 72 h of treatment. Our results revealed that Z2E' and Z2E compounds possessed strong activity (IC50 = 24.8 and 90.9 µg/mL, respectively) against MCF-7 cells at a higher rate than the standard compound 5-FU (IC50 = 97.47 µg/mL). Our results indicated that Z2E' had a promising bioactive scaffold of great medicinal interest due to their numerous pharmacological and biological activities.

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Section: Sulfonamidesmentioning

confidence: 99%

Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

2022

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“…Antimicrobial activity of compounds 19(a-p) was studied against bacterial and fungal strains and observed that highest antimicrobial activity against Escherichia coli (gram negative strain) at MIC of 100 μg/mL was shown by 19b(R = H, R ChemistrySelect bacteria like Staphylococcus aureus and Streptococcus pyogenes. [22] Haeri So et al reported synthesis of a compound namely BQ ((1E,1'E)-N,N'-((1,3-phenylenebis (oxy))bis(3,1phenylene))bis(1-(quinolin-2-yl)methanamine)) (22) which contains quinoline moiety. It was prepared as chromogenic sensor for copper (II) and biological thiols (GSH, Cys, Hcy).…”

Section: Chemistry Of Quinoline Based Heterocycle Scaffoldsmentioning

confidence: 99%

“…For its synthesis condensation reaction was carried out between compound (20) and (21) in the presence of Methyl alcohol. Compound BQ (22) shows optical variations to Cu (II) ion as quinoline moiety act as chromophore and functional group. Also, for biological thiols Cu (II) shows high affinity.…”

Section: Chemistry Of Quinoline Based Heterocycle Scaffoldsmentioning

confidence: 99%

“…Compound 19 k (R=−CH 3 , R 1 =4‐OCH 3 ) possessed good antibacterial activity against Pseudomonas aeruginosa (gram negative strain) at MIC OF 200 μg/mL. 19j(R=CH 3 , R 1 =4‐CH 3 ) and 19k(R=−CH 3 , R 1 =4‐OCH 3) were active against fungal strains like Candida albicans , Aspergillus niger and Aspergillus clavatus at MIC 200 μg/mL and these compounds did not show same activity trend on gram positive bacteria like Staphylococcus aureus and Streptococcus pyogenes [22] …”

Section: Introductionmentioning

confidence: 99%

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Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

et al. 2022

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Quinoline is a significant scaffold among heterocyclic compounds and can be used as a key building block for the development of novel medications. Quinoline and its derivatives are recognised as biologically active substances with a number of pharmacological properties. Nowadays, quinolinebased heterocycle scaffolds have achieved a prominent position in medicinal chemistry due to their significant pharmaco-logical and biological properties. The discovery and creation of cutting-edge medications to treat a variety of diseases is an example of the usefulness of these compounds. The current study outlines the range of methods available to create different quinolone-based heterocycle scaffolds and their advantageous therapeutic applications using the literature that has been published up to 2022.

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“…[7][8][9][10][11][12][13][14] The other heterocycles like pyrimidine, furan, pyrrole, indole, oxadiazole, benzoxazole, azetidine, thiophene, coumarin, benzofuran, pyrazole, quinoline oxazole, quinazoline, pyrimidine, thiazole, quinoline, pyrazole, and isoxazole also possess various pharmacological activities. [8,[15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] The Food and Drug Administration (FDA)-approved drugs in recent years contain biologically active heterocycles in their structures. The drugs like remdesivir (broad-spectrum antiviral drug), [31] avaprinitib (an antitumor drug), [32] pematinib (an anticancer drug used to treat cholangiocarcinoma), [33] remimazolam (sedative drug), [34] and oliceradine (pain medication) [35] approved in 2020 (Figure 1).…”

mentioning

confidence: 99%

Oxadiazole: A highly versatile scaffold in drug discovery

Desai

Monapara

Jethawa

et al. 2022

Archiv der Pharmazie

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As a pharmacologically important heterocycle, oxadiazole paved the way to combat the problem associated with the confluence of many commercially available drugs with different pharmacological profiles. The present review focuses on the potential applications of five-membered heterocyclic oxadiazole derivatives, especially 1,2,4-oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole, as therapeutic agents. Designing new hybrid molecules containing the oxadiazole moiety is a better solution for the development of new drug molecules. The designed molecules may accumulate a biological profile better than those of the drugs currently available on the market. The present review will guide the way for researchers in the field of medicinal chemistry to design new biologically active molecules based on the oxadiazole nucleus. Antitubercular, antimalarial, anti-inflammatory, anti-HIV, antibacterial, and anticancer activities of various oxadiazoles have been reviewed extensively here.

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Synthesis, Antimicrobial Capability and Molecular Docking of Heterocyclic Scaffolds Clubbed by 2-Azetidinone, Thiazole and Quinoline Derivatives

Cited by 14 publications

References 45 publications

Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

Oxadiazole: A highly versatile scaffold in drug discovery

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