17823-28-8Relevant academic research and scientific papers
Heterocyclic tautomerism: Reassignment of two crystal structures of 2-amino-1,3-thia-zolidin-4-one derivatives
Gzella, Andrzej K.,Kowiel, Marcin,Suse?, Aneta,Wojtyra, Magdalena N.,Lesyk, Roman
, p. 812 - 816 (2014)
The structures of 5-(2-hy-droxy-ethyl)-2-[(pyridin-2-yl)amino]-1,3-thia- zolidin-4-one, C10H11N3O2S, (I), and ethyl 4-[(4-oxo-1,3-thia-zolidin-2-yl) amino]-benzoate, C12H12N2O3S, (II), which are identical to the entries with refcodes GACXOZ [Váňa et al. (2009). J. Heterocycl. Chem. 46, 635-639] and HEGLUC [Behbehani & Ibrahim (2012). Mol-ecules, 17, 6362-6385], respectively, in the Cambridge Structural Database [Allen (2002). Acta Cryst. B58, 380-388], have been redetermined at 130 K. This structural study shows that both investigated compounds exist in their crystal structures as the tautomer with the carbonyl-imine group in the five-membered heterocyclic ring and an exocyclic amine N atom, rather than the previously reported tautomer with a secondary amide group and an exocyclic imine N atom. The physico-chemical and spectroscopic data of the two investigated compounds are the same as those of GACXOZ and HEGLUC, respectively. In the thia-zolidin-4-one system of (I), the S and chiral C atoms, along with the hy-droxy-ethyl group, are disordered. The thia-zolidin-4-one fragment takes up two alternative locations in the crystal structure, which allows the mol-ecule to adopt R and S configurations. The occupancy factors of the disordered atoms are 0.883 (2) (for the R configuration) and 0.117 (2) (for the S configuration). In (I), the main factor that determines the crystal packing is a system of hydrogen bonds, involving both strong N - H?N and O - H?O and weak C - H?O hydrogen bonds, linking the mol-ecules into a three-dimensional hydrogen-bond network. On the other hand, in (II), the mol-ecules are linked via N - H?O hydrogen bonds into chains.
4-Thiazolidinones in heterocyclic synthesis: Synthesis of novel enaminones, azolopyrimidines and 2-arylimino-5-arylidene-4-thiazolidinones
Behbehani, Haider,Ibrahim, Hamada Mohamed
experimental part, p. 6362 - 6385 (2012/08/28)
The 4-thiazolidinones 3a-d were used as a key intermediates for the synthesis of 2-arylimino-5-arylidene-4-thiazolidinones derivatives 7a-p via nucleophilic addition reactions with the arylidene malononitrile. Moreover the 4-thiazolidinones 3a and 3c condensed with the DMF-DMA to form the corresponding enamines 8 and 9 depending on the reaction conditions. Otherwise the 4-thiazolidinone 3b reacts regioselectively with DMF-DMA to afford the enaminones 10 and 11, respectively. The latter reacts with many heterocyclic amines affording polyfunctionally substituted fused pyrimidine derivatives 13-18. The enamine 8b was also reacted with the 3-amino-1,2,4-triazole to afford the acyclic product 19, which could not be further cyclized to the corresponding tricyclic system 20. Moreover the 4-thiazolidinone 3c reacted with the benzenediazonium chloride to afford the arylhydrazones 12. The X-ray single crystal technique was employed in this study for structure elucidation and Z/E potential isomerism configuration determination. The X-ray crystallographic analyses of eight products could be obtained, thus establishing with certainty the structures proposed in this work.
Design, synthesis, cytoselective toxicity, structure-activity relationships, and pharmacophore of thiazolidinone derivatives targeting drug-resistant lung cancer cells
Zhou, Hongyu,Wu, Shuhong,Zhai, Shumei,Liu, Aifeng,Sun, Ying,Li, Rongshi,Zhang, Ying,Ekins, Sean,Swaan, Peter W.,Fang, Bingliang,Zhang, Bin,Yan, Bing
, p. 1242 - 1251 (2008/12/23)
Ten cytoselective compounds have been identified from 372 thiazolidinone analogues by applying iterative library approaches. These compounds selectively killed both non-small cell lung cancer cell line H460 and its paclitaxel-resistant variant H460taxR at an IC50 between 0.21 and 2.93 μM while showing much less toxicity to normal human fibroblasts at concentrations up to 195 μM. Structure-activity relationship studies revealed that (1) the nitrogen atom on the 4-thiazolidinone ring (ring B in Figure 1) cannot be substituted, (2) several substitutions on ring A are tolerated at various positions, and (3) the substitution on ring C is restricted to the -NMe2 group at the 4-position. A pharmacophore derived from active molecules suggested that two hydrogen bond acceptors and three hydrophobic regions were common features. Activities against P-gp-overexpressing and paclitaxel-resistant cell line H460taxR and modeling using a previously validated P-gp substrate pharmacophore suggested that active compounds were not likely P-gp substrates.
