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Synthesis, Anticancer, and Antibacterial Studies of Benzylidene Bearing 5-substituted and 3,5-disubstituted-2,4-Thiazolidinedione Derivatives


Navjot Singh Sethi, Deo Nandan Prasad and Rajesh K. Singh*   Pages 1 - 12 ( 12 )


Aim: To develop novel compounds having potent anticancer and antibacterial activities.

Background: Several studies have proved that benzylidene analogues of clinical 2,4-TZDs such as troglitazone and ciglitazone have more potent antiproliferative activity than their parent compounds. Literature studies also revealed that attachment of more heterocyclic rings containing nitrogen on 5th position of 2,4-TZD can enhance the antimicrobial activity. Hence, attachment of various moieties on benzylidene ring may produce safe and effective compounds in future.

Objective: The objective of the present study is to synthesize a set of novel benzylidene ring containing 5- and 3- substituted-2,4-thiazolidinedione derivatives and evaluated for their anticancer and antibacterial activity.

Method: The synthesized compounds were characterized by IR, NMR, mass and elemental studies. The in vitro cytotoxicity studies were performed for human breast cancer (MCF-7) and human lung cancer (A549) cells and HepG2 cell-line and compared to standard drug doxorubicin by MTT assay. Antimicrobial activity of the synthesized 2,4-thiazolidinediones derivatives was carried out using the cup plate method with slight modification.

Result: The results obtained showed that TZ-5 and TZ-13 exhibited good antiproliferative activity against A549 cancer cell-line whereas TZ-10 exhibited moderate antiproliferative activity against HepG2 cell-line when compared to standard drug doxorubicin. TZ-5 also exhibited reasonable activity against MCF-7 cell-line against doxorubicin as standard. TZ-4, TZ-5, TZ-6, TZ-7 and TZ-16 exhibited remarkable antibacterial activity against Gram +ive and moderate activity against Gram –ive bacteria against standard drug ciprofloxacin.

Conclusion: Attachment of heterocyclic rings containing nitrogen as the hetero atom improves the anticancer and antimicrobial potential. Attachment of electronegative element like halogens can also enhance the antimicrobial activity. Further structure modifications may lead to the development of more potent 2,4-TZD leads that can be evaluated for further advanced studies.


2, 4-Thiazolidinedione, Anticancer, Antibacterial, Structure-activity relationship, MTT assay


School of Pharmacy, Maharaja Agrasen University, Atal Shiksha Kunj, Kalujhanda, Dist. Solan, 174103, Himachal Pradesh, Department of Pharmaceutical Chemistry, Shivalik College of Pharmacy, Nangal, Dist. Rupnagar, 140126, Punjab, Department of Pharmaceutical Chemistry, Shivalik College of Pharmacy, Nangal, Dist. Rupnagar, 140126, Punjab

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