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Demonic axe-like conjugated alkynes in combating microbes
Jayaram Reddy Komsani1, Satish Koppireddi, Sreenivas Avula
1Fluoroorganics Division, CSIR-Indian Institute of Chemical Technology (IICT), Tarnaka, Hyderabad 500607, Andhra Pradesh, India.
European Journal of Medicinal Chemistry
|August 27, 2013
Summary
New disubstituted alkynes show potent antimicrobial activity against various bacteria and fungi. These compounds, derived from β-oxo-alkylidenetriphenylphosphoranes, offer potential for novel antimicrobial drug development.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Microbiology
Background:
- β-oxo-alkylidenetriphenylphosphoranes are precursors to various organic compounds.
- Conjugated alkynes and phosphoranes possess diverse biological activities.
- Antimicrobial resistance necessitates the development of new therapeutic agents.
Purpose of the Study:
- To synthesize a new series of disubstituted alkynes.
- To evaluate the in vitro antimicrobial potential of synthesized alkynes and their phosphorane precursors.
- To identify potent antimicrobial agents against a panel of bacteria and fungi.
Main Methods:
- Microwave-induced internal splitting of β-oxo-alkylidenetriphenylphosphoranes to yield disubstituted alkynes.
- In vitro antimicrobial assays against Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis, Staphylococcus epidermidis), Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae), and fungal strains (Aspergillus niger, Candida albicans, Aspergillus flavus, Candida rugosa, Saccharomyces cerevisiae).
Main Results:
- A series of disubstituted alkynes were successfully synthesized.
- The 3-pyridylalkyne derivatives demonstrated high potency against most tested microorganisms.
- Notable activity was observed against Staphylococcus aureus, Bacillus subtilis, Staphylococcus epidermidis, Pseudomonas aeruginosa, Klebsiella pneumoniae, Aspergillus niger, Candida albicans, Aspergillus flavus, Candida rugosa, and Saccharomyces cerevisiae.
- E. coli showed resistance to the tested compounds.
Conclusions:
- The synthesized disubstituted alkynes, particularly 3-pyridylalkyne derivatives, exhibit significant antimicrobial properties.
- These compounds represent promising candidates for further investigation as novel antimicrobial drugs.
- The synthetic methodology provides an efficient route to potentially bioactive alkynes.
Keywords:
Alkyl halopyridylpropynoic acid esterAntimicrobial activityHalopyridylpropynenitrileiso-Propyl bromotriphenylphosphoranylacetic acid esterα-Nicotinoyl-α-(alkoxycarbonyl)methylenetriphenylphosphoranesβ-Oxo-alkylidene-triphenylphosphoranesMore Related Videos
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