Novel O‐Alkylated Chromones as Antimicrobial Agents: Ultrasound Mediated Synthesis, Molecular Docking and ADME Prediction

Dofe, Vidya S.; Sarkate, Aniket P.; Lokwani, Deepak K.; Shinde, Devanand B.; Kathwate, Santosh H.; Gill, Charansing H.

doi:10.1002/jhet.2868

Cited by 21 publications

(7 citation statements)

References 27 publications

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“…Regarding ultrasound-based methods for O -alkylation of heterocyclic compounds, existing protocols have described the treatment of 3-hydroxychromones [ 18 ] or 5-hydroxychromone [ 19 ] with alkyl(allyl) halides in the presence of potassium carbonate (K 2 CO 3 ) as the base for the synthesis of the desired products. In these procedures, dimethylformamide (DMF) and N -methylpyrrolidinone were used as solvents to furnish the compounds with satisfactory yields.…”

Section: Resultsmentioning

confidence: 99%

Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates

et al. 2021

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Tuberculosis (TB) has been described as a global health crisis since the second half of the 1990s. Mycobacterium tuberculosis (Mtb), the etiologic agent of TB in humans, is a very successful pathogen, being the main cause of death in the population among infectious agents. In 2019, it was estimated that around 10 million individuals were contaminated by this bacillus and about 1.2 million succumbed to the disease. In recent years, our research group has reported the design and synthesis of quinoline derivatives as drug candidates for the treatment of TB. These compounds have demonstrated potent and selective growth inhibition of drug-susceptible and drug-resistant Mtb strains. Herein, a new synthetic approach was established providing efficient and rapid access (15 min) to a series of 4-alkoxy-6-methoxy-2-methylquinolines using ultrasound energy. The new synthetic protocol provides a simple procedure utilizing an open vessel system that affords the target products at satisfactory yields (45–84%) and elevated purities (≥95%). The methodology allows the evaluation of a larger number of molecules in assays against the bacillus, facilitating the determination of the structure–activity relationship with a reduced environmental cost.

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Section: Resultsmentioning

confidence: 99%

Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates

et al. 2021

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“…These infections are very common in patients immunocompromised by aggressive therapies for certain diseases, including diabetes, cancer, and HIV/AIDS [33]. o-Hydroxyaryl ketones are versatile building blocks for the preparation of benzopyrans such as chromones and isoflavones, for which antifungal effects have been described [8,26,[34][35][36]. The test compounds were fungicidal, since the use of resazurin revealed no redox metabolism in fungal cells at the reported MIC.…”

Section: In Vitro Antimicrobial Activitymentioning

confidence: 99%

Synthesis Of Alkoxy-Isoflavones As Potential α-Glucosidase Inhibitors

Aguila-Muñoz

Cervantes-Espinoza

Escalante

et al. 2022

Preprint

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The aim of the present study was to synthesize isoflavone-enaminones 3a-c and 7-alkoxy-isoflavones 4a-c, evaluate their inhibition of a-glucosidase, and analyze the bioisosteric effect of the presence versus absence of aromatic moieties in these benzopyran derivatives. All the test compounds exhibited a greater inhibition of a-glucosidase than the positive control acarbose. The series of isoflavones 3a-c and 4a-c showed a higher inhibitory activity (IC50 = 6.3 - 87.6 µM) than the parental 7-hydroxyisoflavones 2a-c (IC50 = 109.4 - 173.2 µM), suggesting that the attachment of a 4’-chloroacetophenone moiety to the 7-hydroxyl group of 2a-c is an efficient way to increase the inhibition of a-glucosidase. Furthermore, the aromatic moieties of the series of compounds 3 and 4 enhance the inhibitory activity by hydrophobic effects according to docking calculations.

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“…Similarly, the complex structures were recaptured from the virtual screening result and the same method was iterated. An excel sheet was xed to investigate all the a nities, hydrogen interaction, steric energy and high re-rank score to recognize the best inhibitor [104][105][106][107][108][109][110][111][112].…”

Section: Drug-drug Comparative Studymentioning

confidence: 99%

Structure-Based Virtual Screening, Molecular Docking, MolecularDynamics Simulation of VEGF Inhibitors for the Clinical Treatment of Ovarian Cancer

Mukherjee

Abdalla

Yadav³

et al. 2021

Preprint

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VEGF and its receptor play an important role both in physiologic and pathologic angiogenesis, which is identified in ovarian cancer progression and metastasis development. The aim of the present investigation is to identify a potential VEGF inhibitor which is playing a crucial role in stimulating the immunosuppressive microenvironment in tumour cells of ovary and to examine for an effectiveness of identified inhibitor for treatment of ovarian cancer using various In silico approaches. 12 established VEGF inhibitors were collected from various literature. The compound AEE788 displays the great affinity towards the target protein as a result of docking study. AEE78 was further used for structure base virtual screening in order to obtain more structurally similar compound with high affinity. Among the 80 Virtual screened compounds, CID 88265020, explicates much better affinity than established compound AEE788. Based on Molecular Dynamics Simulation, pharmacophore and comparative toxicity analysis of both the best established compound and the best virtual screened compound displayed a trivial variation in associated properties. The virtual screened compound CID 88265020 have the high affinity with the lowest re-rank score, and holds a huge potential to inhibit the VGFR and can be implemented for prospective of future investigations in Ovarian Cancer.

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Novel O‐Alkylated Chromones as Antimicrobial Agents: Ultrasound Mediated Synthesis, Molecular Docking and ADME Prediction

Cited by 21 publications

References 27 publications

Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates

Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates

Synthesis Of Alkoxy-Isoflavones As Potential α-Glucosidase Inhibitors

Structure-Based Virtual Screening, Molecular Docking, MolecularDynamics Simulation of VEGF Inhibitors for the Clinical Treatment of Ovarian Cancer

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