Spirochromone-chalcone conjugates as antitubercular agents: synthesis, bio evaluation and molecular modeling studies

Mujahid, Mohammad; Yogeeswari, Perumal; Sriram, Dharmarajan; Basavanag, Unnamatla M. V.; Díaz-Cervantes, Erik; Córdoba-Bahena, Luis; Robles, Juvencio; Gonnade, Rajesh G.; Karthikeyan, Muthukumarasamy; Vyas, Renu; Muthukrishnan, M.

doi:10.1039/c5ra21737g

Cited by 37 publications

(12 citation statements)

References 32 publications

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“…All the docked conformations for the synthesized compounds were found with the most favorable docking poses by means of a maximum number of The preface SAR of the chalcone annulated pyrazoline conjugates reveals that compounds are possessing electron-withdrawing groups such as halogen, nitro atoms in its aromatic ring favor better activity (P1, P2, & P5). This is maybe due to its high electronegativity and the presence of a lone pair of an electron with this substitution (Mujahid et al, 2015).…”

Section: Results Of the Docking Simulation Studymentioning

confidence: 99%

Dual evaluation of some novel chalcone annulated pyrazolines as anti-inflammatory and antimicrobial agents via in-silico target study on cyclooxygenase-2

Prabha¹,

Selvaraj

Selvamani³

et al. 2019

ijrps

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A novel series of chalcone bearing pyrazoline moieties were (P1 to P7) synthesized and characterized by various analytical techniques. The anti-inflammatory studies showed the compounds P1, P2, P5, and P6 have produced the noteworthy inhibition on protein denaturation (81.39 - 96.57 %) when compared to standard 98.17% whereas, the antiproteinase activity was in the range of 84.55- 90.44 % when compared to the standard, 95.95 %. The compounds, P1, P2, P5 (2-Cl, 4- Cl & -NO2 substituent) bearing electron-withdrawing groups and the compounds P3 & P6 (4-N(CH3)2 & -OH substituent) possessing electron-donating group in its phenyl ring system exhibited the prominent activity. Further, to explore the molecular mechanism, the in-silico docking study against COX-2 enzyme was performed. The compounds were also screened for their antibacterial activities. Among them, the compounds P1, P2, P3, P5 and P6 showed the significant antibacterial activity against both gram-positive and gram-negative pathogen such as, Bacillus cereus, Staphylococcus aureus, Serratia marcescens and Staphylococcus typhi with maximum zone of inhibition within the range of 12-14 mm and 19-25 mm for 100 and 200 µg/ml concentrations respectively when compared to that of standard drug Gentamycin, whose ranges between 15-18 mm and 25-28 mm correspondingly.

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Section: Results Of the Docking Simulation Studymentioning

confidence: 99%

Dual evaluation of some novel chalcone annulated pyrazolines as anti-inflammatory and antimicrobial agents via in-silico target study on cyclooxygenase-2

Prabha¹,

Selvaraj

Selvamani³

et al. 2019

ijrps

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“…Spirochromone annulated chalcone conjugates (43) were documented for antitubercular activity against Mycobacterium tuberculosis H37Rv strain. Molecular docking studies performed against the receptors revealed MTB phosphotyrosine phosphatase B protein as the most probable target based on the high bindingaffinity scores [44].…”

Section: Antitubercular Chalconesmentioning

confidence: 99%

Biological Role of Chalcones in Medicinal Chemistry

Tekale¹,

Mashele²,

Pooe³

et al. 2020

Vector-Borne Diseases - Recent Developments in Epidemiology and Control

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Chalcones are promising synthons and bioactive scaffolds of great medicinal interest due to their numerous pharmacological and biological activities. They are well recognized to possess antimicrobial, anticancer, antitubercular, antioxidant, anti-inflammatory, antileishmanial, and other significant biological activities. This chapter highlights recent updates and applications of chalcones as biologically, pharmacologically, and medicinally important entities.

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“…Due to the wide range of biological and medicinal activities the synthesis of spiro compounds has become a significant target over the past decade. 1 H ‐indole‐2,3‐diones (isatins) are important core structures, able to form a large number of both naturally occurring and synthetic spiroheterocycles and know to exhibit several biological activities like antiinflammatory, and laxative agents, antibacterial, antimicrobial, antimalaria, antitumor, antitubercular, and anti‐HIV …”

Section: Introductionmentioning

confidence: 99%

TiO₂ Nanoparticles Immobilized on Carbon Nanotubes: An Efficient Heterogeneous Catalyst in Cyclocondensation Reaction of Isatins with Malononitrile and 4‐Hydroxycoumarin or 3,4‐Methylenedioxyphenol under Mild Reaction Conditions

Abdolmohammadi

Nasrabadi

Dabiri

et al. 2020

Applied Organom Chemis

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TiO2 nanoparticles supported on carbon nanotubes (TiO2‐CNTs) as an efficient heterogeneous catalyst was used for the synthesis of spiro[3,4′]1,3‐dihydro‐2H‐indol‐2‐one‐2′‐amino‐5′‐oxo‐4'H,5'H‐pyrano[3′,2′‐c]chromen‐3′‐yl cyanides and spiro[3,8′]1,3‐dihydro‐2H‐indol‐2‐one‐6′‐amino‐8'H‐[1′,3′]dioxolo[4′,5′‐g]chromen‐7′‐yl cyanides via the cyclocondensation reaction of isatins with malononitrile and 4‐hydroxycoumarin or 3,4‐methylenedioxyphenol in aqueous media at room temperature. This reaction offers several sustainable and economic benefits such as high yields of products, convenient operation, and use of non‐toxic catalyst in water media.

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Spirochromone-chalcone conjugates as antitubercular agents: synthesis, bio evaluation and molecular modeling studies

Abstract: We report new spiro chromone scaffold derived molecules possessing in vitro anti-tubercular activities. QSAR based molecular modeling studies correlated the bioactivities with the frontier molecular orbital energies.

Cited by 37 publications

References 32 publications

Dual evaluation of some novel chalcone annulated pyrazolines as anti-inflammatory and antimicrobial agents via in-silico target study on cyclooxygenase-2

Dual evaluation of some novel chalcone annulated pyrazolines as anti-inflammatory and antimicrobial agents via in-silico target study on cyclooxygenase-2

Biological Role of Chalcones in Medicinal Chemistry

TiO₂ Nanoparticles Immobilized on Carbon Nanotubes: An Efficient Heterogeneous Catalyst in Cyclocondensation Reaction of Isatins with Malononitrile and 4‐Hydroxycoumarin or 3,4‐Methylenedioxyphenol under Mild Reaction Conditions

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Spirochromone-chalcone conjugates as antitubercular agents: synthesis, bio evaluation and molecular modeling studies

Abstract: We report new spiro chromone scaffold derived molecules possessing in vitro anti-tubercular activities. QSAR based molecular modeling studies correlated the bioactivities with the frontier molecular orbital energies.

Cited by 37 publications

References 32 publications

Dual evaluation of some novel chalcone annulated pyrazolines as anti-inflammatory and antimicrobial agents via in-silico target study on cyclooxygenase-2

Dual evaluation of some novel chalcone annulated pyrazolines as anti-inflammatory and antimicrobial agents via in-silico target study on cyclooxygenase-2

Biological Role of Chalcones in Medicinal Chemistry

TiO2 Nanoparticles Immobilized on Carbon Nanotubes: An Efficient Heterogeneous Catalyst in Cyclocondensation Reaction of Isatins with Malononitrile and 4‐Hydroxycoumarin or 3,4‐Methylenedioxyphenol under Mild Reaction Conditions

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TiO₂ Nanoparticles Immobilized on Carbon Nanotubes: An Efficient Heterogeneous Catalyst in Cyclocondensation Reaction of Isatins with Malononitrile and 4‐Hydroxycoumarin or 3,4‐Methylenedioxyphenol under Mild Reaction Conditions