18623-60-4Relevant academic research and scientific papers
Synthesis and Primary Antitumor Screening of 4-[5-(1H-Indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides
Horishny, V. Ya.,Matiychuk, V. S.
, p. 1146 - 1152 (2020)
Abstract: A preparative procedure was developed for the synthesis of 4-[5-(1-R-1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acids which were converted to acid chlorides, and the latter reacted with aromatic and heterocycli
A novel class of inhibitors of peptide deformylase discovered through high-throughput screening and virtual ligand screening
Howard, Michael H.,Cenizal, Teodorica,Gutteridge, Steven,Hanna, Wayne S.,Tao, Yong,Totrov, Maxim,Wittenbach, Vernon A.,Zheng, Ya-Jun
, p. 6669 - 6672 (2004)
Peptide deformylase (PDF) has been identified as a promising antibacterial and herbicide target. A structurally novel class of inhibitors containing a 2-thioxo-thiazolidin-4-one heterocycle substituted by an arylidene group at the 5-position and a hexanoi
The Crystal Structures of Three Rhodanine-3-Carboxylic Acids
Tejchman, Waldemar,Skórska-Stania, Agnieszka,?es?awska, Ewa
, p. 181 - 187 (2016)
Abstract: The rhodanine derivatives show various pharmacological activities. Rhodanine-3-carboxylic acids can be used as the substrates in various synthesis of compounds containing rhodanine-3-carboxyalkyl moiety. In this paper new crystal structures of rhodanine-3-acetic acid and its two homologues, i.e. rhodanine-3-propionic acid and rhodanine-3-butyric acid, are reported. The relationship between the length of the alkyl chain and the geometry of these molecules was studied. The crystal network is dominated by strong hydrogen bonds O–H···O formed by the carboxyl groups. Additionally, weak C–H···O and C–H···S contacts are observed. Graphical Abstract: To study the difference in intermolecular interactions of rhodanine-3-carboxylic acid, three crystal structures were determined by X-ray diffraction method. The crystal network in all studied structures is built of homosynthons and stabilized by weak C–H···O and C–H···S contacts.[Figure not available: see fulltext.]
Spectral Characteristic and Preliminary Anticancer Activity in vitro of Selected Rhodanine-3-carboxylic Acids Derivatives
Stawoska, Iwona,Tejchman, Waldemar,Mazuryk, Olga,Ly?ka, Antonín,Nowak-Sliwinska, Patrycja,?es?awska, Ewa,Nitek, Wojciech,Kania, Agnieszka
, p. 2889 - 2897 (2017)
Selected rhodanine-3-carboxylic acids derivatives were synthesized to determine the influence of the structure and the length of the linker between the carboxyl group and the nitrogen atom (N-3) in the 2-thioxo-4-thiazolidinone ring on their activity, monitored via interactions with human serum albumin. Based on fluorescence studies, we concluded that the length of the linker has a limited impact on these interactions. Additionally, we proposed the static mechanism of quenching for all the tested compounds. These derivatives seem to possess an anticancer activity in the nanomolar range with 3 as the most potent compound in both A2780 and A2780cisR cell lines.
5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)alkancarboxylic Acids as Antimicrobial Agents: Synthesis, biological evaluation, and molecular docking studies
Ciric, Ana,Geronikaki, Athina,Glamoclija, Jasmina,Horishny, Volodymyr,Kartsev, Victor,Matiychuk, Vasyl,Petrou, Anthi,Sokovic, Marina
, (2020/04/29)
Background: Infectious diseases symbolize a global consequential strain on public health security and impact on the socio-economic stability all over the world. The increasing resistance to the current antimicrobial treatment has resulted in crucial need for the discovery and development of novel entity for the infectious treatment with different modes of action that could target both sensitive and resistant strains. Methods: Compounds were synthesized using classical methods of organic synthesis. Results: All 20 synthesized compounds showed antibacterial activity against eight Gram-positive and Gram-negative bacterial species. It should be mentioned that all compounds exhibited better antibacterial potency than ampicillin against all bacteria tested. Furthermore, 18 compounds appeared to be more potent than streptomycin against Staphylococcus aureus, Enterobacter cloacae, Pseudomonas aeruginosa, Listeria monocytogenes, and Escherichia coli. Three the most active compounds 4h, 5b, and 5g appeared to be more potent against MRSA than ampicillin, while streptomycin did not show any bactericidal activity. All three compounds displayed better activity also against resistant strains P. aeruginosa and E. coli than ampicillin. Furthermore, all compounds were able to inhibit biofilm formation 2- to 4-times more than both reference drugs. Compounds were evaluated also for their antifungal activity against eight species. The evaluation revealed that all compounds exhibited antifungal activity better than the reference drugs bifonazole and ketoconazole. Molecular docking studies on antibacterial and antifungal targets were performed in order to elucidate the mechanism of antibacterial activity of synthesized compounds. Conclusion: All tested compounds showed good antibacterial and antifungal activity better than that of reference drugs and three the most active compounds could consider as lead compounds for the development of new more potent agents.
Discovery of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors
Sun, Liangpeng,Wang, Peipei,Xu, Lili,Gao, Lixin,Li, Jia,Piao, Huri
, p. 1187 - 1193 (2019/03/26)
Two series of 1,3-diphenyl-1H-pyrazole derivatives containing rhodanine-3-alkanoic acid groups were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, IIIv was found to have the best in vitro inhibition activity against PTP1B (IC50 = 0.67 ± 0.09 μM) and the best selectivity (9-fold) between PTP1B and T-cell protein tyrosine phosphatase (TCPTP). Molecular docking studies demonstrated that compounds IIIm, IIIv and IVg could occupy simultaneously at both the catalytic site and the adjacent pTyr binding site. These results provide novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs.
Antibacterial properties of 5-substituted derivatives of rhodanine-3-carboxyalkyl acids
Tejchman, Waldemar,Korona-Glowniak, Izabela,Malm, Anna,Zylewski, Marek,Suder, Piotr
, p. 1316 - 1324 (2017/05/04)
A series of rhodanine 3-carboxyalkanoic acid derivatives possessing 4′-(N,N-dialkyl-amino or diphenylamino)-benzylidene moiety as a substituent at the C-5 position were synthesised and their antibacterial activity was screened. All the rhodanine derivatives showed bacteriostatic or bactericidal activity to the reference gram-positive bacterial strains, but lack of activity to the reference Gram-negative bacterial strains and yeast strains was observed.
2-THIOXOTHIAZOLIDIN-4-ONE DERIVATIVES ACTIVE AS TRANSTHYRETIN LIGANDS AND USES THEREOF
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Paragraph 00318; 00319, (2016/06/15)
Compounds of formula (II) are provided for stabilizing protein transthyretin (TTR) and inhibiting amyloid fibril formation, for example, transthyretin-mediated amyloid fibril formation, and for treating, preventing, or ameliorating one or more symptoms of amyloid diseases, for example, transthyretin-related amyloidosis (ATTR).
