48 Citations (Scopus)

Abstract

As an important class of compounds, 2-quinolones are isomeric to 4-quinolones and isosteric to coumarins. The compounds that have 2-quinolone moiety are associated with interesting biologic activities such as antibacterial, anticancer, antiviral, cardiotonic, and N-methyl-D-aspartate receptor inhibitor functions, among others. In the current study, based on the rational approach, lead molecules of the 2-quinolone skeleton were designed for binding to the bacterial DNA gyrase subunit A. Docking simulations and quantitative structure activity relationship (QSAR) analysis were performed using the Molegro Virtual Docker and Sarchitech softwares. Based on these studies, the 7-amino-4-methylquinolin-2(1H)-one parent compound and its carboxamides (JST 1-15) were synthesized using Conrad Limpach synthesis. The synthesized test compounds then were characterized by thin-layer chromatography and melting point determination, as well as by ultraviolet, infrared (IR), 1H-NMR, and MS studies. All synthesized and purified compounds were tested for antioxidant and antibacterial activity.

Original languageEnglish
Pages (from-to)193-209
Number of pages17
JournalMedicinal Chemistry Research
Volume19
Issue number2
DOIs
Publication statusPublished - 03-2010

Fingerprint

Antioxidants
4-Quinolones
DNA Gyrase
Cardiotonic Agents
Coumarins
Thin layer chromatography
Bacterial DNA
Quantitative Structure-Activity Relationship
Thin Layer Chromatography
N-Methyl-D-Aspartate Receptors
Skeleton
Freezing
Antiviral Agents
Melting point
Software
Nuclear magnetic resonance
Infrared radiation
Molecules
carbostyril
4-amino-2-methylquinoline

All Science Journal Classification (ASJC) codes

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

Cite this

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title = "Design and synthesis of 2-quinolones as antioxidants and antimicrobials: A rational approach",
abstract = "As an important class of compounds, 2-quinolones are isomeric to 4-quinolones and isosteric to coumarins. The compounds that have 2-quinolone moiety are associated with interesting biologic activities such as antibacterial, anticancer, antiviral, cardiotonic, and N-methyl-D-aspartate receptor inhibitor functions, among others. In the current study, based on the rational approach, lead molecules of the 2-quinolone skeleton were designed for binding to the bacterial DNA gyrase subunit A. Docking simulations and quantitative structure activity relationship (QSAR) analysis were performed using the Molegro Virtual Docker and Sarchitech softwares. Based on these studies, the 7-amino-4-methylquinolin-2(1H)-one parent compound and its carboxamides (JST 1-15) were synthesized using Conrad Limpach synthesis. The synthesized test compounds then were characterized by thin-layer chromatography and melting point determination, as well as by ultraviolet, infrared (IR), 1H-NMR, and MS studies. All synthesized and purified compounds were tested for antioxidant and antibacterial activity.",
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Design and synthesis of 2-quinolones as antioxidants and antimicrobials : A rational approach. / Jayashree, B. S.; Thomas, Seeja; Nayak, Yogendra.

In: Medicinal Chemistry Research, Vol. 19, No. 2, 03.2010, p. 193-209.

Research output: Contribution to journalArticle

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T1 - Design and synthesis of 2-quinolones as antioxidants and antimicrobials

T2 - A rational approach

AU - Jayashree, B. S.

AU - Thomas, Seeja

AU - Nayak, Yogendra

PY - 2010/3

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