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New phenolic Mannich bases with piperazines and their bioactivities
Halise Inci Gul1, Mehtap Tugrak1, Mustafa Gul2
1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey.
Bioorganic Chemistry
|June 22, 2019
Summary
New Mannich bases were synthesized and evaluated for anticancer and carbonic anhydrase (CA) inhibitory effects. Compounds 2 and 8 showed high potency selectivity expression, while compounds 3 and 5 exhibited significant CA inhibition, indicating potential as lead compounds.
Area of Science:
- Medicinal Chemistry
- Organic Synthesis
- Biochemistry
Background:
- Mannich bases are versatile scaffolds in drug discovery.
- Carbonic anhydrase (CA) enzymes are implicated in various diseases, making them therapeutic targets.
- Indanone derivatives have shown promising biological activities.
Purpose of the Study:
- To synthesize novel Mannich bases derived from a vanillin-based chalcone.
- To evaluate the synthesized compounds for cytotoxic/anticancer and carbonic anhydrase inhibitory activities.
- To identify potential lead compounds for further drug development.
Main Methods:
- Synthesis of Mannich bases via the reaction of a vanillin-derived chalcone, paraformaldehyde, and various substituted piperazine amines.
- Evaluation of cytotoxic/anticancer activity.
- Inhibition assays against human carbonic anhydrase I (hCA I) and human carbonic anhydrase II (hCA II).
Main Results:
- Eight novel Mannich bases were successfully synthesized and characterized.
- Compounds 2 and 8 demonstrated the highest potency selectivity expression (PSE) values.
- Compounds 3 and 5 exhibited the lowest inhibition constants (Ki) against hCA I and hCA II, respectively.
Conclusions:
- Compounds 2 and 8 possess significant cytotoxic/anticancer activity.
- Compounds 3 and 5 show potent inhibitory effects against hCA I and hCA II, respectively.
- These compounds represent promising starting points for the development of new therapeutic agents.
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