Synthesis of novel 1,3-thiazin-4-ones by acetylene diester cyclization and their anticancer activities

GRAPHICAL ABSTRACT

ABSTRACT

A novel series of 1,3-thiazin-4-one derivatives containing a piperidyl ring (7–16) were designed and synthesized efficiently by thioamide and acetylene diester cyclization reaction via aminolysis of the ester group and the elimination of an alcohol molecule. The structures of all the novel compounds were established by their FTIR, Mass, ¹H NMR, and ¹³C NMR spectral techniques. The newly synthesized compounds (7–16) were studied for their in vitro anticancer activity against human liver cancer cell lines Hep G2 using MTT assay. The IC₅₀ values of the tested compounds were ranging in between 7.48 ± 0.71 and 56.57 ± 1.37 µM. Further, the apoptosis evaluation by the mitochondrial membrane potential using JC-1 dye was carried out and the results are in good agreement with the cytotoxicity studies.

KEYWORDS:

• 1,3-Thiazin-4-one
• acetylene diesters
• in vitro
• apoptosis
• cytotoxicity

Funding

The authors gratefully acknowledge the funding support from University Grants Commission (UGC) Grant No. 39-689-2010 SR, New Delhi, India.