Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates

2-Oxo-2H-chromenylpyrazolecarboxylates (8a–h and 12a–zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a–h and 11a–w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H)-ones (13i–n) were prepared from corresponding phenylhydrazones (7a–h) with...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2013-07, Vol.65, p.389-402
Main Authors: Kumar, J. Ashok, Saidachary, G., Mallesham, G., Sridhar, B., Jain, Nishant, Kalivendi, Shashi Vardhan, Rao, V. Jayathirtha, Raju, B. China
Format: Article
Language:English
Subjects:
2-Oxo-2H-chromenylpyrazolecarboxylates
[3+2] Cycloaddition
Anticancer activity
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Benzopyrans - pharmacology
Cell Line, Tumor
Cell Proliferation - drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
HeLa Cells
Humans
Models, Molecular
Molecular Structure
Phenylchromeno[4,3-c]pyrazol-4(1H)-ones
Photochemical Processes
Structure-Activity Relationship
UV and fluorescence studies
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Summary:2-Oxo-2H-chromenylpyrazolecarboxylates (8a–h and 12a–zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a–h and 11a–w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H)-ones (13i–n) were prepared from corresponding phenylhydrazones (7a–h) with catalytic amount of piperidine in presence of pyridine as a solvent at 100 °C. All the synthesized compounds (8a–h, 12a–zb and 13a–n) were screened for anticancer activity against three human cancer cell lines such as prostate (DU-145), lung adenocarcinoma (A549), and cervical (HeLa) by standard MTT assay method. Further, photophysical properties (UV and fluorescence) for these compounds were discussed. [Display omitted] [3 + 2] Cycloaddition of 2H-chromenophenylhydrazones with diethyl/dimethylbut-2-ynedioates afforded 2H-chromenylpyrazolecarboxylates/phenylchromenopyrazolones. All the compounds were screened for their anticancer activity, among these, compounds 8c and 12g were displayed very good anticancer activity. •A series of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates/phenylchromeno[4,3-c]pyrazol-4(1H)-ones were synthesized.•The anticancer activity was performed on three human cancer cell lines by using standard MTT assay method.•UV and fluorescence properties were discussed.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2013.03.042