Facile Synthesis and Antibacterial, Antitubercular, and Anticancer Activities of Novel 1,4-Dihydropyridines

A series of twenty new 4‐substituted‐2,6‐dimethyl‐3,5‐bis‐N‐(heteroaryl)‐carbamoyl‐1,4‐dihydropyridines have been prepared from a three‐component one‐pot condensation reaction of N‐heteroaryl acetoacetamide, an aromatic/heteroaromatic aldehyde, and ammonium acetate under four different experimental...

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Bibliographic Details
Published in:Archiv der Pharmazie (Weinheim) 2010-06, Vol.343 (6), p.342-352
Main Authors: Sirisha, Kalam, Achaiah, Garlapati, Reddy, Vanga Malla
Format: Article
Language:English
Subjects:
1,4‐Dihydropyridines
4-Dihydropyridines
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Anticancer activity
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antitubercular activity
Antitubercular Agents - chemical synthesis
Antitubercular Agents - chemistry
Antitubercular Agents - pharmacology
Cell Line, Tumor
Cell Proliferation - drug effects
Dihydropyridines - chemical synthesis
Dihydropyridines - chemistry
Dihydropyridines - pharmacology
Drug Resistance, Bacterial - drug effects
Gram-Negative Bacteria - drug effects
Gram-Positive Bacteria - drug effects
Humans
Microbial Sensitivity Tests
Microwave irradiation
Molecular Structure
Mycobacterium tuberculosis - drug effects
N-Heteroaryl acetoacetamide
Structure-Activity Relationship
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Summary:A series of twenty new 4‐substituted‐2,6‐dimethyl‐3,5‐bis‐N‐(heteroaryl)‐carbamoyl‐1,4‐dihydropyridines have been prepared from a three‐component one‐pot condensation reaction of N‐heteroaryl acetoacetamide, an aromatic/heteroaromatic aldehyde, and ammonium acetate under four different experimental conditions. Except for the conventional method, all the experimental conditions were simple, eco‐friendly, economical, and the reactions were rapid and high‐yielding. The methods employed have been compared in terms of yields, cost, and simplicity. The synthesized compounds were characterized by different spectroscopic techniques and evaluated for their in‐vitro anticancer, antibacterial, and antitubercular activities. Amongst the compounds tested, compound 25 exhibited the highest anticancer activity while compounds 14 and 18 exhibited significant antibacterial and antitubercular activities.
ISSN:0365-6233
1521-4184
DOI:10.1002/ardp.200900243