Synthesis and Cytotoxic Evaluation of Novel Spirohydantoin Derivatives of the Dihydrothieno[2,3-b]naphtho-4,9-dione System

Abstract

The synthesis and cytotoxic evaluation of 3-(alkyl)(alkyl-substituted)spiro[(dihydroimidazo-2,4-dione)-5,3'-(2',3'-dihydrothieno[2,3-b]naphtho-4',9'-dione)]derivatives are described. Evaluation of these analogues against the MCF-7 human breast carcinoma and SW 620 human colon carcinoma cell lines uncovered for most of the compounds a cytotoxic potency comparable to or greater than that of doxorubicin. Compound 15 exhibited remarkable cytotoxic activity against several other human solid tumor cell lines. Interestingly, only a partial cross-resistance to compound 15 in selected tumor cell sublines known to be resistant to doxorubicin (MCF-7/Dx and A2780/Dx) was observed, whereas a total absence of cross-resistance in a tumor cell subline selected for resistance to cisplatin was found (A2780/DDP).

Synthesis and in vitro cytotoxic evaluation of novel diazaspiro bicyclo hydantoin derivatives in human leukemia cells: A SAR study

“…In particular, spirohydantoin derivatives represent a potential starting point in discovering new and potent antitumoral agents with cytotoxic activity on ovarian and breast cancer [4]. Hydantoin derivatives also exhibit antidepressant, antiviral, antithrombotic activities as well as inhibitory activity against some enzymes (human aldose reductase and human leucocyte elastase) [5].…”

Dihydrithieno[2,3-b]naphto-4,9-dione analogues as anticancer agents: Synthesis and in cell pharmacological studies

“…To this aim, we first verified the effect of the stereochemistry of the chiral centre at C-3 on the activity of 14. The two enantiomerically pure compounds, 14(þR) and 14(¡S) were prepared as reported elsewhere [21,24]. Treatment of LN299 cells with 0.6 mM of 14, 14(þ) and 14(À) induced a cytotoxic effect resulting in 50, 48, 50% cell death, respectively (see supporting information).…”

Synthesis and characterization of novel anti-inflammatory poly(spiro thiazolidinone)s

“…[9][10][11] Thiazolidinone derivatives have been shown to have high activity in vitro against mycobacterium tuberculosis and as drugs to treat HIV and cancer. [11][12][13] The combination of nitrogen or sulfur atoms in five-or six-membered heterocyclic ring caused diverse biological effects, [14][15][16][17][18][19][20][21][22][23][24] this increase the importance of thiazolidinone as a class of N and S including heterocyclic compounds, which are broadly used as key building blocks in the field of pharmaceutical agents and drugs. [25] According to our best of knowledge, there are no reported examples in the literature for such spirothiazolidinone polymers or polyspiro macromolecules.…”