Synthesis and Biological Evaluation of 1,3,4-Thiadiazole Linked Phthalimide Derivatives as Anticancer Agents

Rezaei, Zahra; Moghimi, Setareh; Javaheri, Rezvan; Asadi, Mehdi; Mahdavi, Mohammad; Shabani, Shabnam; Edraki, Najmeh; Firuzi, Omidreza; Safavi, Maliheh; Amini, Mohsen; Asadipour, Ali; Zeinalzadeh, Elnaz; Firoozpour, Loghman; Foroumadi, Alireza

doi:10.2174/1570180814666170127164759

Cited by 17 publications

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“…Rezaei and co-workers described synthesis and biological investigations of 1,3,4-thiadiazole-linked phthalimide derivatives (2017). The compounds were evaluated for their anticancer activity against human colon cancer HT-29 and human breast cancer MCF-7 cell lines, by MTT assay; the compound containing a 4-nitrobenzoyl moiety ( 62) ( Figure 32 ) has shown the best anticancer activity, with IC 50 = 23.83 and 27.21 μM, respectively [ 41 ].…”

Section: Derivatives Of 25-disubstituted-134-thiadiazolementioning

confidence: 99%

Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review

2020

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Section: Derivatives Of 25-disubstituted-134-thiadiazolementioning

confidence: 99%

Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review

2020

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“…Some of them have been shown to have promising anticancer activity, exceeding the reference drugs in tests. Many studies have demonstrated the activity of compounds from this group against breast cancer cell lines ( Figure 1 ) [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. Therefore, we assumed that the search for cytotoxic compounds in the group of simple 2,5-disubstituted 1,3,4-thiadiazole derivatives is a promising direction of research.…”

Section: Introductionmentioning

confidence: 99%

New 1,3,4-Thiadiazole Derivatives with Anticancer Activity

et al. 2022

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We designed and synthesized the 1,3,4-thiadiazole derivatives differing in the structure of the substituents in C2 and C5 positions. The cytotoxic activity of the obtained compounds was then determined in biological studies using MCF-7 and MDA-MB-231 breast cancer cells and normal cell line (fibroblasts). The results showed that in both breast cancer cell lines, the strongest anti-proliferative activity was exerted by 2-(2-trifluorometylophenylamino)-5-(3-methoxyphenyl)-1,3,4-thiadiazole. The IC50 values of this compound against MCF-7 and MDA-MB-231 breast cancer cells were 49.6 µM and 53.4 µM, respectively. Importantly, all new compounds had weaker cytotoxic activity on normal cell line than on breast cancer cell lines. In silico studies demonstrated a possible multitarget mode of action for the synthesized compounds. The most likely mechanism of action for the new compounds is connected with the activities of Caspase 3 and Caspase 8 and activation of BAX proteins.

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“…On the other hand, phthalimides, have exhibited remarkable pharmacological effects, including anti-inflammatory, antimycobacterial, analgesic, anticonvulsant, and anticancer activities ( 20 21 22 23 ). Some derivatives of thiadiazole and triazole containing phthalimide pharmacophore were reported as anticancer agents ( 24 25 26 ). The synthesis of some derivatives of naphthalimide substituted triazole with a high affinity towards DNA has been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxic activity evaluation of some new 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4- triazole derivatives attached to phthalimide

et al. 2021

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Background and purpose: In the last few decades, nitrogen-rich heterocyclic compounds such as 1, 3, 4-thiadiazoles, 1, 2, 4-triazoles and 1, 3, 4-oxadiazoles have received considerable attention because of their notable biological properties, especially cytotoxic effects. The small molecules of mentioned azole derivatives revealed very intensive antitumor activity. In addition, phthalimide-thiadiazole and naphthalimide-triazole hybrid derivatives have shown remarkable cytotoxic effects. According to these observations, some of the hybrid derivatives containing the phthalimide-five-membered azoles were prepared in three steps in this research. Experimental approach: The thiol group of azoles was treated with ethyl chloroacetate which was followed by a reaction with hydrazine hydrate to provide acid hydrazide derivatives. Subsequently, the corresponding acid hydrazides were utilized to prepare the final derivatives through the reaction with phthalic anhydride. Cytotoxic activity of final compounds was evaluated against MCF-7 and HeLa cell lines using MTT assay. Findings/Results: Compound 3d containing two phthalimide moieties in its structure showed a significant improvement in cytotoxic activity with an IC 50 value of 29 μM against HeLa cell line. Compounds 3a-3c showed less cytotoxic effects against both cell lines. Conclusion and implications: The combination of the thiadiazole nucleus with two phthalimide structures increased the cytotoxic activity against the HeLa cell line. This increase in cytotoxic activity is probably due to its being more lipophilic characteristic and interaction of this derivative with the biological targets of two directions.

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Synthesis and Biological Evaluation of 1,3,4-Thiadiazole Linked Phthalimide Derivatives as Anticancer Agents

Cited by 17 publications

References 0 publications

Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review

Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review

New 1,3,4-Thiadiazole Derivatives with Anticancer Activity

Synthesis and cytotoxic activity evaluation of some new 1, 3, 4-oxadiazole, 1, 3, 4-thiadiazole and 1, 2, 4- triazole derivatives attached to phthalimide

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