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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.]

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Research speed reading in 2021. Application of 7025-19-6, Modeling chemical reactions helps engineers virtually understand the chemistry, optimal size and design of the system, and how it interacts with other physics that may come into play. In a document type is Patent, and a compound is mentioned, 7025-19-6, 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, introducing its new discovery.

The present invention provides a carbazole derivative, its preparation method and in anti-tumor applications, carbazole derivatives having formula I structure, R1 And R2 Independently selected from hydrogen, halogen, alkoxy, C1 – C4 alkyl, halogenated alkyl, nitro and nitrile in the one or more; R3 Selected from carboxyl, methyl, phenyl or cyano; X is CH2 Or carbonyl; m=0 – 3; n=0 – 3. The derivatives inhibit topoisomerase II activity; it is non-built-in type of Topo II catalytic inhibitors, can be used for preparing topoisomerase II as the target of the anti-tumor drug; it can inhibit the multi-tumor cell strain proliferation, can be used for the preparation of anticancer drugs. Carbazole derivatives in 2.5 – 20mumol/L under the topoisomerase II have a strong inhibiting effect; the sub-cervical cancer cells, lung cancer cells, human leukemia cells and human prostate cancer cell has strong inhibiting effect. (by machine translation)

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Breaking up the crowd: The pathological aggregation of tau protein correlates closely with the progression of Alzheimer’s disease. Rhodanine-based inhibitors of tau aggregation (e.g. 1) have been identified, and it has been shown that tau aggregation in a cell model is reversible and can be inhibited by small molecules at nanomolar concentrations (see SEM images). (Chemical Equation Presented)

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A series of rhodanine incorporated quinoline derivatives were efficiently synthesized using reusable DBU acetate as ionic liquid and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Ra (MTB) (ATCC 25177) and Mycobacterium bovis BCG (ATCC 35743) both in active and dormant state. Compounds 3e, 3f, 3g, 3h and 3i exhibited very good antitubercular activity. The active compounds were studied for cytotoxicity against HUVEC, THP-1, macrophages, A549, PANC-1 and HeLa cell lines using modified MTT assay and were found to be noncytotoxic. Inactivity of all these compounds against Gram positive and Gram negative bacteria indicates their specificity towards the MTB. Further, the synthesized compounds have been screened for their in vitro antifungal activity. In addition, the molecular docking studies revealed the binding modes of these compounds in active site of Zmp1 enzyme, which in turn helped to establish a structural basis of inhibition of mycobacteria. The results of present study clearly indicate the identification of some novel, selective and specific inhibitors against MTB that can be explored further for potential antitubercular drug.

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Disclosed are an organic dye having a specific structure, a photoelectric conversion material containing the dye, a semiconductor electrode formed of a substrate having an electrically conductive surface, a semiconductor layer coated on the electrically conductive surface and the above dye adsorbed on the surface, and a photoelectric conversion device to which the above dye is applied.The present invention uses the above dye and can therefore provide a photoelectric conversion device excellent in photoelectric conversion efficiency, and the photoelectric conversion device is suitable for use in a solar cell or the like.

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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.

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The pantothenate biosynthetic pathway is essential for the persistent growth and virulence of Mycobacterium tuberculosis (Mtb) and one of the enzymes in the pathway, pantothenate synthetase (PS, EC: 6.3.2.1), encoded by the panC gene, has become an appropriate target for new therapeutics to treat tuberculosis. Herein, we report nanomolar thiazolidine inhibitors of Mtb PS developed by a rational inhibitor design approach. The thiazolidine compounds were discovered by using energy-based pharmacophore modelling and subsequent in vitro screening, which resulted in compounds with a half maximal inhibitory concentration (IC50) value of (1.12±0.12) muM. These compounds were subsequently optimised by a combination of modelling and synthetic chemistry. Hit expansion of the lead by chemical synthesis led to an improved inhibitor with an IC50 value of 350 nM and an Mtb minimum inhibitory concentration (MIC) of 1.55 muM. Some of these compounds also showed good activity against dormant Mtb cells. Let sleeping cells lie: Mycobacterium tuberculosis pantothenate synthetase (Mtb PS) has become a target for new therapeutics to treat tuberculosis. Nanomolar thiazolidine inhibitors of Mtb PS were developed by rational inhibitor design involving modelling, in vitro screening and optimisation. Hit expansion of the lead by synthesis led to an improved inhibitor with an IC50 value of 350 nM and an Mtb MIC value of 1.55 muM. Some of these compounds also showed good activity against dormant Mtb cells.

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Six focused rhodanine-based libraries, 60 compounds in total, were synthesized and evaluated as potential dynamin I GTPase inhibitors. Twenty-six were more potent than the lead compound with 13 returning IC50 values ?10 muM, making the Rhodadyn series among the most active dynamin inhibitors reported. Two analogues were highly effective at blocking receptor-mediated endocytosis: C10 and D10 with IC50(RME) = 7.0 ± 2.2 and 5.9 ± 1.0 muM, respectively. These compounds are equipotent with the best reported in-cell dynamin inhibitors.

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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 hexanoic acid side chain at the 3-position was discovered independently via high-throughput screening and virtual ligand screening. Data mining and analogue synthesis established a structure-activity relationship for the side chain region that is consistent with the docked structure.

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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 muM) 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.

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Reference:
Quinuclidine – Wikipedia,
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