Synthesis, Antimicrobial and Antitubercular Activities of Some Novel Trihydroxy Benzamido Azetidin-2-one Derivatives

doi:10.4314/TJPR.V10I2.66567

Paper

Synthesis, Antimicrobial and Antitubercular Activities of Some Novel Trihydroxy Benzamido Azetidin-2-one Derivatives

Published May 25, 2011 · K. Ilango, S. Arunkumar

Tropical Journal of Pharmaceutical Research

Q3 SJR score

21

Citations

1

Influential Citations

Full textSemantic Scholar

Abstract

Purpose: To synthesize and characterize novel trihydroxy benzamido azetidin-2-one derivatives and screen them for antimicrobial and antitubercular activities. Methods: A series of novel 4-aryl-3-chloro-N-(3,4,5-trihydroxy benzamido)-2-azetidinones, 3a-o, were synthesized by reacting various Schiff bases of galloyl hydrazide, 2a-o, with chloroacetyl chloride in the presence of dioxan and triethylamine. Schiff bases of galloyl hydrazide, 2a-o, were synthesized from galloyl hydrazide. The newly synthesized compounds were characterized by infrared spectroscopy (IR), mass spectroscopy (MS) and proton nuclear magnetic spectroscopy ( 1 H NMR) and elemental analysis; they were also screened for in vitro antibacterial, antifungal and antitubercular activities. Ciprofloxacin and ketoconazole were used as reference standards for antibacterial and antifungal activities, respectively, while isoniazid was used as reference standard for antitubercular activity. Results: Compounds 3f, 3g and 3o with chlorophenyl group and compound 3k with 4-dimethyl amino phenyl group exhibited good antimicrobial activity. Also, compounds 3f, 3g, 3k and 3o showed antitubercular activity with minimum inhibitory concentration (MIC) values equivalent to the standard drug (isoniazid). MIC values of 3f, 3g, 3k and 3o were 0.76, 0.57.0.62 and 0.83 µg/ml, respectively, while the MIC of isoniazid was 0.56. Conclusion: We report the successful synthesis, spectral characterization, as well as in vitro antimicrobial and antitubercular evaluation of a series of novel trihydroxy benzamido azetidin-2-one derivatives. The work shows the emergence of new antimicrobial and antitubercular compounds.

In Vitro Study

Study Snapshot

Novel trihydroxy benzamido azetidin-2-one derivatives show promising antimicrobial and antitubercular activities, with MIC values equivalent to standard drugs.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Synthesis, Antimicrobial and Antitubercular Activities of Some Novel Trihydroxy Benzamido Azetidin-2-one Derivatives

Sign up to use Study Snapshot

References

Identification of phenolic compounds and appraisal of antioxidant and antityrosinase activities from litchi (Litchi sinensis Sonn.) seeds

Litchi seeds, particularly 50% ethanol extract, show high antioxidant capacity and antitryrosinase activity, making them a potential source of natural antioxidants.

Synthesis and Pharmacological Evaluation of Azetidin-2-ones and Thiazolidin-4-ones Encompassing Benzothiazole

Synthesis and pharmacological evaluation of various 7-chloro-6-fluoro-2-arylidenylaminobenzo(1,3)thiazole compounds show potential for antiinflammatory, analgesic, CNS depressant, and skeletal muscle relaxant activities.

Direct and indirect antimicrobial effects and antioxidant activity of Cordia gilletii De Wild (Boraginaceae).

Cordia gilletii De Wild root bark exhibits antimicrobial and antioxidant properties, supporting its traditional use in treating infectious diseases and wounds.

β-Lactams in synthesis: short syntheses of cobactin analogs

A new method for synthesizing cobactin analogs, with potential anti-TB activity, is presented, involving single-step coupling reactions between amines and cyanide-activated -lactams.

Synthesis and in vitro and in vivo antimycobacterial activity of isonicotinoyl hydrazones.

Isonicotinoyl hydrazones show potential as new antimycobacterial agents, with compound 8 showing the most activity against M. tuberculosis strain H(37)R(v) and being as effective as isoniazid.

Citations

The application of hydrazones and hydrazide-hydrazones in the synthesis of bioactive azetidin-2-one derivatives: A mini review.

Hydrazones and hydrazide-hydrazones are useful intermediates in the synthesis of bioactive azetidin-2-one derivatives, which show antibacterial, antitubercular, and antifungal properties, as well as anti-inflammatory, antioxidant, and anticonvulsant properties

Exploring Azatidinone Moiety: An Insight into its Anti-tubercular Potency

Azatidinones show potent antitubercular activity, potentially offering a new treatment for multi-drug resistant tuberculosis.

Evaluation and Docking Study of Pyrazine Containing 1, 3, 4-Oxadiazoles Clubbed with Substituted Azetidin-2-one: A New Class of Potential Antimicrobial and Antitubercular

Synthesized oxadiazole derivatives show potential antibacterial, antifungal, and antitubercular activity against various microorganisms, with 7b and 7g showing the highest activity.

Synthesis, Characterization and in vitro Antimicrobial Screening of Some Novel Series of 2-Azetidinone Derivatives Integrated with Quinoline, Pyrazole and Benzofuran Moieties

Novel 2-azetidinone derivatives synthesized with Quinoline, Pyrazole, and Benzofuran moieties show promising in vitro antibacterial activity against pathogenic bacteria like S. aureus and E. coli.

Accurate conventional and microwave-assisted synthesis of galloyl hydrazide

This research presents a new one-pot solventless greener microwave-assisted method and a traditional conventional heating method for synthesis of galloyl hydrazide, providing accurate identification and characterization data for pharmaceutical chemistry.

Synthesis and biological evaluation of 2,4,5-trisubstituted thiazoles as antituberculosis agents effective against drug-resistant tuberculosis.

Trisubstituted thiazoles, 13h and 13p, show potential as effective antituberculosis agents against drug-resistant tuberculosis, with 13p showing activity against multidrug-resistant isolates.

Chemoenzymatic Approach toward the Synthesis of 3-O-(α/β)-Glucosylated 3-Hydroxy-β-lactams

Enzymatic glycosylation of -lactam alcohols enables efficient preparation of 3-O-(/)-glucosylated 3-Hydroxy--lactams, contributing to sustainable green chemistry processes.

New structural classes of antituberculosis agents

New structural classes of anti-TB agents have been discovered, potentially reducing resistance development and improving potency and specificity in combating TB.

Biological potential of thiazolidinedione derivatives of synthetic origin

Thiazolidinedione derivatives show potential as anti-malarial, antimicrobial, anti-mycobacterium, anticonvulsant, antiviral, anticancer, anti-inflammatory, antioxidant, and antitubercular agents.