Design, synthesis and characterization of fluoro substituted novel pyrazolylpyrazolines scaffold and their pharmacological screening

A novel series of fluoro substituted pyrazolylpyrazolines 7a–l was synthesized in good to excellent yield (77–88%) from pyrazole chalcones 5a–d and substituted phenyl hydrazine hydrochlorides 6a–c under microwave irradiation. The newly synthesized compounds were screened for their preliminary in vit...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2014-09, Vol.84, p.51-58
Main Authors: Karad, Sharad C., Purohit, Vishal B., Raval, Dipak K.
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Antimalarial activity
Antimalarials - chemical synthesis
Antimalarials - chemistry
Antimalarials - pharmacology
Antimicrobial activity
Antituberculosis activity
Bacteria - drug effects
Dose-Response Relationship, Drug
Drug Design
Fungi - drug effects
Microbial Sensitivity Tests
Microwave irradiation
Molecular Structure
Parasitic Sensitivity Tests
Plasmodium falciparum - drug effects
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Pyrazoles - pharmacology
Pyrazolylpyrazolines
Structure-Activity Relationship
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Summary:A novel series of fluoro substituted pyrazolylpyrazolines 7a–l was synthesized in good to excellent yield (77–88%) from pyrazole chalcones 5a–d and substituted phenyl hydrazine hydrochlorides 6a–c under microwave irradiation. The newly synthesized compounds were screened for their preliminary in vitro antibacterial activity against a panel of pathogenic stains of bacteria and fungi, antituberculosis activity against Mycobacterium tuberculosis H37Rv and antimalarial activity against Plasmodium falciparum. Compounds 7a, 7b, 7g, 7h, 7j and 7k displayed excellent activity against P. falciparum stain as compared to quinine IC50 0.268. Good antitubercular activity was exhibited by compounds 7a, 7e, 7h and 7k. Some of them also exhibited superior antibacterial activity as compared to the first line drugs. [Display omitted] •Microwave promoted synthesis of fluorinated pyrazolylpyrazolines is illustrated.•Biological screening of the title compounds has been performed.•SAR study of fluorinated pyrazolylpyrazolines has been discussed.•Compounds 7a, 7b, 7g, 7h, 7j and 7k exhibited superior antimalarial potency.•Compound 7h exhibited interesting dual antimalarial and antituberculosis profile.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2014.07.008