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Updated: Jan 16, 2026
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
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Isoniazid-Derived Hydrazones Featuring Piperazine/Piperidine Rings: Design, Synthesis, and Investigation of
Esma Özcan1, Siva Krishna Vagolu2,3, Rasoul Tamhaev4,5
1Department of Basic Sciences, Faculty of Pharmacy, Erciyes University, 38039 Kayseri, Turkey.
Biomolecules
|September 27, 2025
Summary
Researchers chemically modified isoniazid (INH) to combat drug-resistant tuberculosis (TB). New INH-based hydrazones showed promising antimycobacterial activity and low toxicity, with compound IP11 being the most effective against resistant Mycobacterium tuberculosis strains.
Area of Science:
- Medicinal Chemistry
- Microbiology
- Drug Discovery
Background:
- Tuberculosis (TB) remains a leading infectious disease globally.
- Emergence of isoniazid (INH)-resistant Mycobacterium tuberculosis (Mtb) strains compromises TB treatment efficacy.
Purpose of the Study:
- To chemically modify INH to overcome INH resistance in Mtb.
- To synthesize and evaluate novel INH-based hydrazones for antimycobacterial activity and safety.
Main Methods:
- Synthesis of INH-based hydrazones (IP1-IP13) via reaction of INH with substituted benzaldehydes.
- Antimycobacterial activity assessed using Microplate Alamar Blue Assay (MABA) against Mtb H37Rv and resistant clinical isolates.
- Cytotoxicity evaluation and InhA inhibition assays performed.
Main Results:
- Compounds IP7-IP13, with increased lipophilicity, demonstrated promising antitubercular activity and low cytotoxicity.
- IP11 exhibited the lowest minimum inhibitory concentration (MIC) values against all tested Mtb strains.
- While IP11 showed some InhA inhibition, it was not the primary mechanism of action.
Conclusions:
- Novel INH-based hydrazones represent a promising strategy to combat drug-resistant TB.
- Compound IP11 is a potential lead candidate for further development against resistant Mtb.
- Further investigation into the mechanism of action beyond direct InhA inhibition is warranted.
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