Prospective study directed to the synthesis of unsymmetrical linked bis-5-arylidene rhodanine derivatives via “one-pot two steps” reactions under microwave irradiation with their antitumor activity

Abstract

International audienceWe here report on the synthesis of new unsymmetrical linked bis-5-arylidene rhodanine derivatives with stereocontrolled Z-configuration. The 6 steps synthesis was achieved and the key steps are the construction of the two 5-arylidene rhodanine moieties using an “one-pot two-steps” method under microwave dielectric heating in a closed reactor. The intermediates 6, 7 and desired unsymmetrical compounds 9 have been also evaluated for their in vitro inhibition of cell proliferation (Huh7 D12, Caco2, MDA-MB 231, HCT116, and NCI-H727 tumoral cell lines). Two of all compounds have shown potent activity against Huh7 D12, Caco2, and MDA-MB 231

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

“…2-N,N 0 -Disubstituted diamines bearing 5-arylidene-4thiazolidinone moiety 136 (Scheme 69) had shown nanomolar inhibition potency (IC 50 40 nM) towards tyrosine phosphorylationregulated kinases 1A [333]. This result prompted to explore the symmetric 1,2-diamino-linker grafted on N-3 position of two different 5-arylidenerhodanine platforms in order to modulate potential biological activity and led to the synthesis of unsymmetrical linked bis-5-arylidenerhodanine derivatives with anticancer effects [334].…”

Unexpected Synthesis of Novel 3-Allyl-5-(arylidene)-2-thioxo-thiazolidin-4-ones in Reactions of 3-Allylrhodanine with 2-Arylidene-4-methyl-5-oxopyrazolidinium Ylides

“…The 5-arylidene-2-thioxo-1,3-thiazolidinine-4-ones or 5-arylidene rhodanines are considered as ''privileged scaffolds'' in the medicinal chemistry community because they presented a bioactivity in a large range of derivatives [1][2][3][4][5] . For example, these small molecules have been known to possesses a wide range of biological properties such as potent and selective inhibitors of the ''atypical'' dual-specificity phosphatase (DSP)…”

Spectral Characteristic and Preliminary Anticancer Activity in vitro of Selected Rhodanine‐3‐carboxylic Acids Derivatives

“…2‐Thioxo‐4‐thiazolidinone, commonly known as “rhodanine,” as well as its derivatives possesses a broad spectrum of biological activity. Their antidiabetic, antifungal, antimicrobial, pesticidal, antiapoptotic, and anticancer activities are widely reported . The rhodanine moiety, possessing a variously substituted benzylidene group at C‐5, shows a moderate anticancer activity .…”