Synthesis of New Carbazole–Thiazole Analogues and Evaluating their Anticancer Activity

Abstract

Medicinal research has focused on the discovery and progress of anticancer drugs. Carbazole and thiazole are organic heterocyclic compounds that are the building blocks for synthetic and natural pharmaceutical compounds. Thus, this research article involves the synthesis of nine carbazole linked thiazolidinone derivatives from the Knoevenagel reaction of 9-ethylcarbazole-3-carbaldehyde with several thiazolidine-5-one and thiazolin-4-one derivatives. The structures of these compounds were confirmed by spectroscopic tools such as IR, ¹H and ¹³C NMR, and mass spectrometry. The MTT assay, using Cisplatin as a reference drug, was used to test the cytotoxicity of the synthesized carbazole-thiazole analogous against three different cell lines: breast cancer (MCF-7), hepatocellular carcinoma (HepG-2), and colon carcinoma (HCT-116). The 3b and 5c molecules were the most effective antitumor drugs against the three cell lines. Compound 3b has IC₅₀ values of (0.0304 ± 0.001, 0.058 ± 0.002 and 0.047 ± 0.002 µM) for HepG-2, MCF-7, and HCT-116, respectively. When examined on HepG-2, MCF-7, and HCT-116 cell lines, the IC₅₀ values revealed by component 5c were (0.048 ± 0.002, 0.086 ± 0.0025 and 0.06 ± 0.007 µM), respectively.

Graphical Abstract

Keywords:

• Carbazole
• thiazole
• Knoevenagel reaction
• anticancer activity
• MTT assay

Author contributions

The manuscript was written through contributions of all authors and all authors have given approval to the final version of the manuscript.

Disclosure statement

No potential conflict of interest was reported by the author(s).