Plant Archives Volume 20 No. 2, 2020 pp. 6275-6287 e-ISSN:2581-6063 (online), ISSN:0972-5210 SYNTHESIS, CHARACTERIZATION AND IN VITRO ANTICANCER EVALUATION OF 4-(5-(2-(SUBSTITUTED)-4-OXOTHIAZOLIDIN-3-YL)- 1,3,4-THIADIAZOL-2-YL)-PHENYL-ACETATE DERIVED FROM PHENOLIC ALDEHYDE Sandeep Jain 1 , Neetu Chopra 1 * and Sanjeev Kalra 2 1* Department of Pharmaceutical Chemistry, Guru Jambheshwar University of Science & Technology, Hissar (Haryana), India. 2 Rajendra Institute of Technology and Sciences, Sirsa (Haryana), India. Abstract A novel series of 4-(5-(2-(substituted)-4-oxothiazolidin-3-yl)-1, 3, 4-thiadiazol-2-yl) -phenyl-acetate from salicaldehyde was (10a-y) synthesized, Characterized and evaluated against In vitro five bacterial, two fungal, breast cancer (MCF-7) and cervical carcinoma (HeLa) cell line. Among the entire tested analogs, thiazolidinone ring substituted at 2- position with Methoxy pyrazole (10g), trimethoxy benzaldehyde (10h), P- OH (10s), exhibited promising anticancer results against Human breast cell line (MCF-7) with the value of IC 50 7.19 ± 0.16, 8.24 ± 1.36, 9.18 ± 0.24nM as compared to the standard drug doxorubicin (IC 50 2.63 ± 0.17) and against gram positive strain B. subtilis (MIC~4.28 ± 0.26 - 4.25 ± 0.16 µg/ml), S. aureus (3.81 ± 0.12- 3.56 ± 0.26 µg/ml) as compared to Ciprofloxacin(MIC~3.47 ± 0.12 µg/ml). While the compound 10k, 10r and 10w having substitution of ethylated indole, p- N, N Dimethyl, 2, 3, 5 Trimethoxy on Thiazolidinone Skelton exhibited significant result of IC 50 value of 3.61 ± 0.12, 6.12 ± 0.17, 6.29 ± 0.14 µM against Human cervical cancer (HeLa) and against fungal strain C. albicans with MIC value (3.49 ± 0.28µg/ml), 3.64 ± 0.14µg/ml and (MIC~4.13 ± 0.39 µg/ml) as compared to standard Fluconazole drug (3.44 ± 0.28µg/ml) The remaining compounds have shown good to moderate activity against the tested cell lines. Based on results achieved for antimicrobial and anticancer activity, structure activity relationship (SAR) of targeted analogs are discussed. Key words: 4- Thiazolidinone, Thiadiazole, Salicylaldehyde, Synthesis, Cytotoxic activity, antimicrobial evaluation Introduction Cancer is becoming a major cause of human health concerns with increasing the number of patients worldwide. Cervical cancer and breast cancer is the most identified cancer in the female population (Felix et al., 2016). Despite off many types of chemotherapeutic drugs were used for the treatment, although still, there is a challenge to identify safe and effective drug for the cancers. Drug resistance is the major concern observed during treatment. (Abrahamn, et al., 2002). The design and development of new anticancer agents with increased efficiency, less side effective, cost effective, and time concern for the treatment were the major challenges for present researchers. Considering these facts, the development of new chemotherapeutic targets with selective action has to be identified, as many classes of heterocyclic scaffolds were used for the different types of cancers. 4-Thiazolidine derivatives are an important class of heterocyclic compounds having nitrogen and sulfur heteroatom known for their potential pharmaceutical applications. Recently, this framework containing compounds were effective against antimicrobial (Young et al., 2004) antischistosomal activity (Taha et al., 2007) antifungal (Asati et al., 2005), antiinflammatory (Jain et al.,2006), antimalarial (Kristina et al., 2009), herbicidal (Sanemitsu, et al., 2006), antiviral (Eiichi, et al., 2007), antidiabetic (Murugan et al., 2009) and antioxidant activities (Shih et al., 2004), 4-thiazolidinones substituted on 2, 3 position possesses the same spectrum of biological activity including anticancer activity (Gududuru, et al., 2004). Fig. 1. 1, 3, 4-Thiadiazoles have been reported to have *Author for correspondence : E-mail : neetushine.chopra@gmail.com