ChemInform Abstract: Synthesis and Biological Activities of New Hydroxy‐3‐pyrazolyl‐4H‐chromen‐4‐ones and Their O‐Glucosides.

Hatzade, K. M.; Taile, V. S.; Gaidhane, P. K.; Haldar, Animeshchandra G. M.; Ingle, V. N.

doi:10.1002/chin.200849194

Cited by 9 publications

(14 citation statements)

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“…The results of synthetic work have revealed that maximum yield of compounds (12a-h) was obtained in the cases where chromone nucleus was bearing electron-withdrawing groups at C-6 or C-7. All the synthesized compounds were evaluated by spectral analysis, that is, 1 H-NMR, 13 C-NMR, and Mass spectroscopy. The spectral data of the synthesized compounds 12a-h are given below:…”

Section: Resultsmentioning

confidence: 99%

“…The obtained compounds, that is, substituted 2-(Phenylamino)-3-(1Htetrazol-5-yl)-4H-chromen-4-one derivatives (12a-h) were evaluated for their in vitro antimicrobial activities against different strains of bacteria (S. aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli) and fungi (Aspergillus niger and Candida albicans) as per the reported methods [13,27].…”

Section: Pharmacological Activitymentioning

confidence: 99%

“…Chromones are very prone to chemical transformations such as photocycloaddition, photodimerization, photoisomerization, photorearrangement, photo-oxidation reduction, and photocyclization which involve both n→π* and π→π* transitions [12,13]. Further, chromones and bischromones (especially their 3-alkoxy derivatives) have also proven themselves as interesting substrates to study the mechanism of photochemical reactions [14].…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, Molecular Docking, and Evaluation of Chromone Based Tetrazole Derivatives

Chopra¹,

Singh²,

Vk³

et al. 2019

Asian J Pharm Clin Res

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Objectives: The objective of this research work was to design, synthesize, study the molecular docking, and evaluate the antimicrobial activity of some novel substituted 2-(Phenylamino)-3-(1H-tetrazol-5-yl)-4H-chromen-4-one derivatives (12a-h). Methods: In the present work, 3-Formylchromones were transformed into pharmacologically active substituted 2-(Phenylamino)-3-(1H-tetrazol-5- yl)-4H-chromen-4-one derivatives (12a-h) through a multistep reaction. Initially, synthesis of the substituted 4-Oxo-2-(phenylamino)-4H-chromone-3- carbaldehydes (9a-h) was carried out using substituted acetophenones (6a-h) as starting material and by employing an earlier reported method (1,3-dipolar cycloaddition reaction). Then, these synthesized compounds were converted into respective oximes (10a-h).The obtained oximes (10a-h) were further converted into nitriles (11a-h) which were finally subjected to concerted cycloaddition through stepwise addition of neutral or anionic azide species to furnish final substituted 2-(Phenylamino)-3-(1H-tetrazol-5-yl)-4H-chromen-4-one derivatives (12a-h). All the newly synthesized compounds (12a-h) and a reference compound (ciprofloxacin) were docked into the active site of TyrRS (PDB: 1JIK) by means of the BioPredicta module of VLife MDS. The synthesized compounds (12a-h) were also evaluated in vitro for their antibacterial (against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli bacterial stains) and antifungal activities (against Aspergillus niger and Candida albicans fungal strains) using Zone of Inhibition method. Results: The formation of substituted 2-(Phenylamino)-3-(1H-tetrazol-5-yl)-4H-chromen-4-one derivatives (12a-h) was confirmed through their spectral analysis, that is, 1H-NMR, 13C-NMR, and Mass spectroscopy. During docking study, the recorded molecular binding interactions revealed that all the newly synthesized compounds (12a-h) interacted well with binding site of the enzyme. The synthesized compounds were also evaluated in vitro for their antibacterial (against S. aureus, B. subtilis, P. aeruginosa, and E. coli bacterial stains) and antifungal activities (against A. niger and C. albicans fungal strains). All the synthesized compounds exhibited moderate-to-potent antimicrobial activities. Conclusions: All the synthesized compounds exhibited moderate-to-potent antimicrobial activity.

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Section: Resultsmentioning

confidence: 99%

Section: Pharmacological Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, Molecular Docking, and Evaluation of Chromone Based Tetrazole Derivatives

Chopra¹,

Singh²,

Vk³

et al. 2019

Asian J Pharm Clin Res

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“…are known phytochemical natural products have different pharmacological activities including anticancer, anti-HIV, antimicrobial, antiinflammatory [3,4]. Chalcones are a significant part of plants belonging to the flavonoids family [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structure-activity relationship study: Anticancer chalcones derived from 4'-morpholinoacetophenone

Kurşun‐Aktar¹,

Oruç‐Emre²,

Karaküçük‐İyidoğan³

et al. 2017

mpj

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The aim of this research was to synthesize chalcone derivatives containing morpholine ring and to investigate their antiproliferative activity. The 3-aryl-1-[4-(morpholin-4-yl)phenyl]prop-2-en-1-one derivatives were synthesized and evaluated for their in vitro antiproliferative activities on C6 cells (Rat glioma cell line) and HeLa cells (Human cervix adenocarcinoma), using the BrdU ELISA assay. The calculation of ADME properties of new chalcone derivatives was used by topological polar surface area (TPSA), absorption (ABS%) and Lipinski's rules. Most of the compounds exhibited significantly antiproliferative activity on two cell lines. Among the screened compounds, compound 7, 10, 11 and 12 revealed higher antiproliferative activity than cisplatin which was used as reference drug. Compound 11 on HeLa cell and compound 10 on C6 cell line are the most effective compared with cisplatin. Keywords

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“…So, continuation of our work [32][33][34][35][36][37][38] and keeping view of the various biological activities, it was proposed to synthesize new molecules containing thiazole, azomethine, O-glucoside, and sulfonamide moiety in one frame-work.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐(sulfamoylphenyl)‐4′‐(iminoaryl/hetroaryl)‐4‐(4′′‐hydroxyphenyl)‐thiazoles and their O‐glucosides

Taile

Hatzade

Ingle

2011

Journal of Heterocyclic Chem

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In continuation of our work, we synthesized 2‐(sulfamoylphenyl)‐4′‐amino‐4‐(4″‐hydroxyphenyl)‐thiazole (3a), which were reacted with various (aryl/hetroaryl) aldehyde to form 2‐(sulfamoylphenyl)‐4′‐(iminoaryl/hetroaryl)‐4‐(4″‐hydroxyphenyl)‐thiazoles (4a, 4b, 4c, 4d, 4e, 4f). Glucosylation of compounds (4a, 4b, 4c, 4d, 4e, 4f) have been done by using acetobromoglucose as a glucosyl donor to afford 2‐(sulfamoylphenyl)‐4′‐(iminoaryl/hetroaryl)‐4‐(2,3,4,6‐tetra‐O‐acetyl‐4″‐O‐β‐D‐glucosidoxyphenyl)‐thiazoles (5a, 5b, 5c, 5d, 5e, 5f), further on deacetylation to produce 2‐(sulfamoylphenyl)‐4′‐(iminoaryl/hetroaryl)‐4‐(4″‐O‐β‐D‐glucosidoxyphenyl)‐thiazoles (6a, 6b, 6c, 6d, 6e, 6f). The compounds are confirmed by FTIR, 1H‐NMR, 13C‐NMR, and ES‐Mass spectral analysis. J. Heterocyclic Chem., (2011).

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ChemInform Abstract: Synthesis and Biological Activities of New Hydroxy‐3‐pyrazolyl‐4H‐chromen‐4‐ones and Their O‐Glucosides.

Cited by 9 publications

References 0 publications

Design, Synthesis, Molecular Docking, and Evaluation of Chromone Based Tetrazole Derivatives

Design, Synthesis, Molecular Docking, and Evaluation of Chromone Based Tetrazole Derivatives

Synthesis and structure-activity relationship study: Anticancer chalcones derived from 4'-morpholinoacetophenone

Synthesis of 2‐(sulfamoylphenyl)‐4′‐(iminoaryl/hetroaryl)‐4‐(4′′‐hydroxyphenyl)‐thiazoles and their O‐glucosides

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