Synthesis of fluoro and trifluoromethyl substituents containing novel tetracyclic N-benzylated benzopiperazine fused acridone regioisomers using a greener solvent 2-MeTHF and their DFT studies

Veligeti, Rajkumar; Ramakrishna, D. S.; Madhu, Rajesh; Anireddy, Jaya Shree

doi:10.1016/j.jfluchem.2022.109989

Cited by 21 publications

(7 citation statements)

References 40 publications

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“…Furthermore, compound (75) The antitubercular activity of compounds (78d), (79b), (80b), (81c), and (81d) was superior with compound 80b showing 95 percent inhibition equivalent to that of standard drug rifampicin. (Scheme 16) [31] Nareshvarma Seelam et al reported the development of a new family of fused pyrazolo [30,40 : 4,5] thiazolo [3,2-b], [1,2,4]triazole (86a-h), Isoxazolo [30,40 : 4,5] thiazolo [3,2-b] [1,2,4,]triazole (87a-h) moieties by the reaction of 4-methyl benzoyl thiosemicarbazide with the suitable chemical reagents yielded [1,2,4]-triazole moieties using innovative conventional procedures. By using the crucial intermediate (84), condensation of Ethyl-p-methyl benzoate with thiosemicarbazide at reflux temperature led to the formation of compounds (86a-h) and (87a-h).…”

Section: Ms Komal Saini Has Been Working As Anmentioning

confidence: 99%

“…[1] Over the years many methods have been reported for the synthesis of different heterocyclic compounds but some of them have gained greater importance. These methods include the use of green solvents [2] for environment friendly procedure while some have shown the use of nano compounds as catalyst for the reactions. [3,4] There are various heterocyclic based drugs that are used in the treatment of tuberculosis such as Rifampin, Isoniazid and pyrazinamide etc.…”

Section: Introductionmentioning

confidence: 99%

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A Comprehensive Examination of Heterocyclic Scaffold Chemistry for Antitubercular Activity

Bendi,

Yadav,

Saini

et al. 2024

Chemistry & Biodiversity

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Tuberculosis is a communicable disease which affects humans particularly the lungs and is transmitted mainly through air. Despite two decades of intensive research aimed at understanding and combating tuberculosis, persistent biological uncertainties continue to hinder progress. Nowadays, heterocyclic compounds have proven themselves in effective treatment of tuberculosis because of their wide range of biological and pharmacological activities. Antituberculosis or antimycobacterial agents encompass a broad array of compounds utilized singly or in conjunction to combat Mycobacterium infections, spanning from tuberculosis to leprosy. Here, we summarize the synthesis of various heterocyclic compounds which includes the greener synthetic route as well as use of nano compounds as catalyst along with their anti TB activities.

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Section: Ms Komal Saini Has Been Working As Anmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Comprehensive Examination of Heterocyclic Scaffold Chemistry for Antitubercular Activity

Bendi,

Yadav,

Saini

et al. 2024

Chemistry & Biodiversity

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“…These chalcone products' reactivity was analyzed using Frontier Molecular Orbital (FMO) and Molecular Electrostatic Potential (MEP) computational analysis. [23][24][25][26] In addition, molecular docking was performed to if there is a relation between protein-ligand binding energy and antimicrobial activity. [27]…”

Section: Introductionmentioning

confidence: 99%

An Experimental and Computational Approach to The Microwave‐Assisted Synthesis of 2’‐Hydoxychalcone Derivatives in 1‐Dodecyl‐3‐Methylimidazolium Bromide ([DDMIm]Br) Ionic Liquids

Wahyuningrum,

Nur Pasya,

Eduardus

et al. 2024

ChemistrySelect

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Four derivatives of 2’‐hydoxychalcone were synthesized through Claisen‐Schmidt condensation by combining 2’‐hydroxyacetophenone and four different benzaldehyde derivatives (o‐vanillin, salicylaldehyde, p‐anisaldehyde, and benzaldehyde) in the presence of a base. The reactions took place in an ionic liquid, 1‐dodecyl‐3‐methylimidazolium bromide ([DDMIm]Br), and were facilitated by microwave irradiation. The reactions were completed within 10 to 15 minutes, yielding products with chemical yields ranging from 52.64 % to 83.42 %. The structures of the synthesized products were confirmed using 1H NMR and 13C NMR spectroscopy. Additionally, antimicrobial activity tests demonstrated the effectiveness of specific derivatives against Staphylococcus aureus and Escherichia coli, underscoring the importance of hydroxy and methoxy groups on the aromatic ring in inhibiting microbial growth. These findings provide valuable knowledge for developing chalcone derivatives with improved properties and potential applications in drug discovery. Furthermore, the synthesized products′ reactivity was analyzed using Frontier Molecular Orbital (FMO) and their reactivity site was mapped using Molecular Electrostatic Potential (MEP). Lastly, molecular docking analysis was attempted to explain antibacterial activities from all products. Nonetheless, the molecular docking simulations conducted in this study were inadequate to fully account for the antimicrobial activity observed in all the products.

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Section: Introductionmentioning

confidence: 99%

“…1 Inspired by the important role of fluorinated molecules in drug discovery and development, many efforts have been made to attach the fluorine atom to a variety of bioactive molecules. [14][15][16] On the other hand, podophyllotoxin (Figure 1), a tubulin polymerization inhibitor, has been known as an antitumor agent. 17 4-Azapodophyllotoxins (3), podophyllotoxin derivatives with a nitrogen atom at position C-2 of the podophyllotoxin skeleton, possess pronounced biological activities, for example, inhibition of cancer cell growth, 18 induction of cell cycle arrest in the G2/M phase and apoptosis, 19,20 tubulin polymerization inhibition, 20 and vascular disrupting activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Cytotoxic Evaluation of Fluoro and Trifluoromethyl Substituents Containing Novel Naphthoquinone-Fused Podophyllotoxins

Thành

Phương

Anh

et al. 2022

Natural Product Communications

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A series of novel naphthoquinone-fused podophyllotoxins containing fluoro and trifluoromethyl substituents were synthesized in a medium with good yields using two different synthetic approaches: microwave-assisted four-component reactions of 2-hydroxy-1,4-naphthoquinone, tetronic acid, fluorinated arylaldehydes, and ammonium acetate, and microwave-assisted three-component reactions of 2-amino-1,4-naphthoquinone, tetronic acid, and fluorinated arylaldehydes. The structures of all products were confirmed by spectral analysis. Together, cytotoxicity assessment of the products against four human cancer cell lines (human carcinoma [KB], human hepatocellular carcinoma [HepG2], lung cancer [A549], breast carcinoma [MCF7], and human embryonic kidney [Hek-293]) was performed by MTT assay. Among the obtained compounds, compound 7f turned out to be the most potent anticancer agent with significant cytotoxic activity against KB, HepG2, and MCF cancer cell lines.

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Synthesis of fluoro and trifluoromethyl substituents containing novel tetracyclic N-benzylated benzopiperazine fused acridone regioisomers using a greener solvent 2-MeTHF and their DFT studies

Cited by 21 publications

References 40 publications

A Comprehensive Examination of Heterocyclic Scaffold Chemistry for Antitubercular Activity

A Comprehensive Examination of Heterocyclic Scaffold Chemistry for Antitubercular Activity

An Experimental and Computational Approach to The Microwave‐Assisted Synthesis of 2’‐Hydoxychalcone Derivatives in 1‐Dodecyl‐3‐Methylimidazolium Bromide ([DDMIm]Br) Ionic Liquids

Synthesis and Cytotoxic Evaluation of Fluoro and Trifluoromethyl Substituents Containing Novel Naphthoquinone-Fused Podophyllotoxins

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