Rigid 3D-spiro chromanone as a crux for efficient antimicrobial agents: synthesis, biological and computational evaluation

Elghareeb, F. H.; Kandil, E. M.; Abou-Elzahab, M. M.; Abdelmoteleb, Mohamed; Abozeid, Mohamed A.

doi:10.1039/d1ra03497a

Cited by 2 publications

(1 citation statement)

References 63 publications

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“…They are used as versatile intermediates for the synthesis of many natural products [14][15][16][17][18][19] and constitute interesting building blocks in drug design and organic synthesis [20][21][22][23]. They also exhibit significant biological activities allowing their use as anticancer [24][25][26][27], antifungal and antibacterial [28][29][30][31], anti-inflammatory [32,33], antidiabetic [34,35], anti-leishmanial (caused by protozoan parasites) [36,37], and insecticidal agents [38] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds

et al. 2022

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A novel series of 14 spiropyrrolidines bearing thiochroman-4-one/chroman-4-one, and oxindole/acenaphthylene-1,2-dione moieties were synthesized and characterized by spectroscopic techniques, as well as by three X-ray diffraction studies, corroborating the stereochemistry. Quantum chemical calculations studies, using the DFT approach, were performed to rationalize the stereochemical outcome. These N-heterocycles were evaluated for their antibacterial and antifungal activities against some pathogenic organisms. Several compounds displayed moderate to excellent activity towards the screened microbe strains in the study compared to Amoxicillin (AMX), Ampicillin (AMP), and Amphotericin B. Furthermore, a structural activity relationship (SAR) was established considering the synthesized compounds. Pharmacokinetic studies reveal that these derivatives exhibit an acceptable predictive ADMET profile (Absorption, Distribution, Metabolism, Excretion and Toxicity) and good drug-likeness.

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Section: Introductionmentioning

confidence: 99%

Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds

et al. 2022

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Microwave Facilitated Discovery of Substituted 1,2,4-triazaspiro[4.5] dec-2-en-3-amines: Biological and Computational Investigations

Patel,

Tople

et al. 2023

CMIC

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Background: Tuberculosis is an effectual infectious disease caused by the spread of tubercular bacteria within the lungs via droplets of coughs and sneezes. In 2021, 1.6 million people died due totuberculosis, which is the 13th leading killer disease and 2nd leading after COVID-19 infectious disease. Objective: Many drugs are available as antitubercular drug, but still, requires more efficacious drug molecules with lower toxicity, side effects and small-sized molecules. To fulfill said prospective, computational study such as molecular docking and ADMET studies guides towards an ideal drug molecule with small -sized, unique spiro structures. Methods: Conventional and microwave-initiated Reaction of cyclohexanone, hydrazine carbothioamide, and 2-amino-4-methoxy-6-methyl-1,3,5-triazine affords compound 1, which is subjected to the Schiff base reaction with diverse aldehydes. All structures are defined using IR, 1H NMR, 13C NMR, and mass spectroscopy. The entire series is exposed to in vitro antibacterial and antitubercular and in silico molecular docking and ADMET studies. Results: Compounds 2c and 2b have been established to be potential antibacterial agents, whereas compounds 2d, 2e, 2j, 2k and 2l are extremely effective against tubercular strains. Furthermore, molecular docking of related molecules is performed, and compounds 2d, 2e, 2j, 2k, and 2l have higher affinities toward antitubercular proteins. ADMET parameters such as water solubility, SA score, PCaco2 value, and TPSA values are satisfactory. Conclusion: The microwave method has been proven to be a greener method as compared to the conventional heating method. Comparative results of in vitro analysis are obtained with referenced antibacterial drugs and antitubercular drugs. In silico observations supports their in vitro assessments. Appraisal obtained from the ADMET study leads to the formation of ideal drug molecules.

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Rigid 3D-spiro chromanone as a crux for efficient antimicrobial agents: synthesis, biological and computational evaluation

Abstract: New heterocyclic compounds based upon rigid 3D-spiro chromanone scaffold have been synthesized and evaluated as efficient antimicrobial agents. Molecular docking and QSAR have explained and supported the observed promising antimicrobial activity.

Cited by 2 publications

References 63 publications

Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds

Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds

Microwave Facilitated Discovery of Substituted 1,2,4-triazaspiro[4.5] dec-2-en-3-amines: Biological and Computational Investigations

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