SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF UNDEC-10-ENOIC ACID DERIVATIVES

Manju Kumari* and Ramandeep Kaur

ABSTRACT

Antimicrobial agents are effective in treatment of many types of infections, but their overuse promotes the spread of resistant microorganisms that refuse to obey conventional treatments and complicate patient care. One way to overcome the problem of antibiotic resistance is by synthesizing new and effective antimicrobial agents. Long chain fatty acid hydrazide derivatives possess antibacterial, antifungal, antimycobacterial and antiviral activities. Undec-10-enoic acid (Undecylenic acid) is an eleven carbon straight chain unsaturated fatty acid. It is a natural fungicide used against fungal skin infections, such as athlete's foot, ringworm and jock itch. Inspired by above facts, in present study a series of undec-10-enoic acid hydrazide derivatives have been synthesized successfully in appreciable yield (50-80%) and characterized by their physicochemical (Mp/Bp and Rf value) and spectral (IR and NMR) data. Synthesized derivatives were evaluated for their in vitro antimicrobial activities against Gram-positive S. aureus, B. subtilis and Gram-negative E. coli and antifungal activity against A. fumigatus and A. niger by tube dilution method. Antimicrobial screening results indicated that compounds having NO2 (4 and 15), alkoxy (9, 11 and 12), hydroxyl (7, 8, 10, 11 and 13) groups and phenyl substituted azetidinone ring (15-17) were more active against tested strains, but none of them have antimicrobial activity comparable to standard drug Ciprofloxacin and Fluconazole. Further, the presence of electron-withdrawing p-fluoro phenyl group in azetidinone moiety (16) improved the growth inhibition potency specifically against tested fungal strains, A. fumigatus and A. niger.

Keywords: Undec-10-enoic acid, Hydrazide derivatives, Antimicrobial activity.