Heterocyclic Building Blocks-Thiazolidine

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Multi-target compounds acting in cancer progression: Focus on thiosemicarbazone, thiazole and thiazolidinone analogues

Currently, cancer and its progression to metastasis result in a large number of deaths. The lack of new drugs, appropriate clinical trials for metastasis preventive drugs and incomplete understanding of the molecular machinery are the major obstacles in metastasis prevention and treatment. On the other hand, thiosemicarbazones and their bioisosteres, thiazole and thiazolidinone are recurring in a wide range of biologically active compounds that reach different targets within tumor context and represent a promising start point to access potential candidates in metastatic cancer. Therefore, the search for new lead compounds showing highest anticancer potency and less adverse effects is the major challenger in drug discovery. The search was based from 1994 to 2018, focusing on thiosemicarbazone, thiazole and thiazolidinone cores that allowed us to discuss how the three multi-target motifs have been used for the target-based design and development of anticancer agents. In the lasts years, thiosemicarbazone, thiazole, and thiazolidinone cores are recurrent in many approaches for cancer therapy. In our search, it was verified that due to its biodiversity and versatility the anticancer potential of such structures has been assigned to distinct mechanisms reinforcing the value of these cores in the anticancer drug development. The present article aims point out the current application of thiosemicarbazone, thiazole and thiazolidinone cores in the design of anticancer agents within tumor progression, acting via varied targets such as cathepsins, NDRG1 gene and kinases, showing in vitro tests, in vivo tests and clinical trials. In our search it was possible to verify that thiazole is the most studied and the most important of the three structures. Therefore, we hope to provide new insights and valuable inspiration in the research of new drugs and development and contribute to the management of cancer.

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Quinuclidine – Wikipedia,
Quinuclidine | C7H258N | ChemSpider

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Acetonitrile-mediated synthesis of 2,4-dichloroquinoline from 2-ethynylaniline and 2,4-dichloroquinazoline from anthranilonitrile

2,4-Dichloroquinolines and 2,4-dichloroquinazolines were synthesized from 2-ethynylanilines and anthranilonitriles, respectively, using diphosgene in acetonitrile and heating at 130 C or 150 C for 12 hours. This reaction was applied to the synthesis of 4,6-dichloropyrazolo[3,4-d]pyrimidine (dichloro-9H-isopurine). The postulated mechanism is also described. Georg Thieme Verlag Stuttgart.

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Quinuclidine | C7H896N | ChemSpider

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Asymmetric transfer hydrogenation of ketones using Ru(0) nanoparticles modified by Chiral Thiones

The catalytic asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol by Ru(0) nanoparticles (NPs) obtained by the in-situ reduction of Ru (II) half-sandwich complexes of chiral 2-oxazolidinethiones and 2-thiozolidinethiones was examined and compared with the catalytic activity of Ru(0) NPs formed in-situ by the reduction of [Ru(p-cymene)(Cl)2]2 in presence of optically active ligands such as (S)-4-isobutylthiazolidine-2-thione, (S)-4-Isopropyl-2(?2-pyridinyl)-2-oxazoline, (8S, 9R)-(?)-cinchonidine, (S)-leucinol, (S)-phenylalaninol, and (S)-leucine. Three of the best catalytic systems were then examined for ATH of thirteen aromatic ketones with different electronic and steric properties. A maximum of 24% ee was obtained using NPs generated from the Ru (II) half-sandwich complex with (S)-4-isobutylthiazolidine-2-thione in the TH of acetophenone. The NPs were characterized by TEM and DLS measurements. Kinetic studies and poisoning experiments confirmed that the reaction is catalyzed by the chiral NPs formed in-situ. Complete characterization of the complexes, including the X-ray crystallographic characterization of two complexes, was also carried out.

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Quinuclidine | C7H774N | ChemSpider

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Synthesis and quantum chemical studies on the tautomeric structures of new thiazole and thiadiazine derivatives

New series of thiazoles and thiadiazines incorporated with pyrazole ring were synthesized via the reaction of 2-(1-(4-cyano-1,5-diphenyl-1H-pyrazol-3-yl)ethylidene) hydrazine-carbothioamide or 4-imino-7-methyl- 2,3-diphenyl-2H-pyrazolo[3,4-d]pyridazine-5(4H)-carbothiohydrazide with different reagents. The structures of all tautomeric forms of the newly synthesized compounds were confirmed on the basis of spectral data aided with DFT and semi-empirical calculations.

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Quinuclidine | C7H298N | ChemSpider

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COMPOUNDS WITH DDX3 INHIBITORY ACTIVITY AND USES THEREOF

The present invention relates to the medical use of the compound of formula 1,2,3 or 4

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Quinuclidine – Wikipedia,
Quinuclidine | C7H799N | ChemSpider

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QUINAZOLINE-PYRIDINE DERIVATIVES FOR THE TREATMENT OF CANCER-RELATED DISORDERS

Compounds that inhibit at least one of the A2A and A2B adenosine receptors, and compositions containing the compound and methods for synthesizing the compound, are described herein. Also described are the use of such compounds and compositions for the treatment of a diverse array of diseases, disorders, and conditions, including cancer- and immune-related disorders that are mediated, at least in part, by the adenosine A2A receptor and/or the adenosine A2B receptor.

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Quinuclidine | C7H854N | ChemSpider

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Nitroimidazoles: Part XVI – Some 1-Methyl-4-nitro-5-substituted Imidazoles

Treatment of 1-methyl-4-nitro-5-chloroimidazole (3) with 5-membered lactames, e.g. imidazolidinones, oxazolidinone and thiazolidinone affords N-imidazolyl derivatives (4a-d).Reaction of 3 with imidazole yields 4e; amino derivatives (4f-h) are similarly obtained. 2-Hydroxypyrazine, 4-hydroxyquinazoline and 3,4,5-trichlorophenol and 3 react to form O-derivatives (4i-k).Imidazole (11) is formed from 1-methyl-4-chloro-5-nitroimidazole (10).

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Quinuclidine | C7H232N | ChemSpider

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Electrochemical Oxidative C(sp3)?H/N?H Cross-Coupling for N-Mannich Bases with Hydrogen Evolution

N-Mannich bases are an important structure in various functional molecules. A new protocol to synthesize N-Mannich bases was established through electrochemical external-oxidant-free C(sp3)?H/N?H cross-coupling with hydrogen evolution. Various N-methylanilines were explored in this transformation. Moreover, simple amides, heteroatom-containing amides, and succinimides were well tolerated in moderate-to-good yields. In addition, the electrochemical dehydrogenative C(sp3)?H/N?H cross-coupling could be scaled up to 5 mmol. By using triethyl phosphite as trapping agent, the phosphorylation product was detected. At the same time, kinetic isotope effect experiments showed that the cleavage of the C?H bond is the rate-limiting step.

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Quinuclidine | C7H477N | ChemSpider

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Regioselective synthesis and biological evaluation of novel bis(2-chloroquinolines)

Reaction of substituted 2,4-dichloroquinolines with bisphenol A in the presence of K2CO3 leads to novel bis(2-chloroquinolines) with high regioselectivity. All the synthesized compounds were characterized by use of spectral data. Preliminary evaluation of in-vitro antibacterial activity against a variety of Gram-positive and Gram-negative organisms was also conducted.

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Quinuclidine | C7H925N | ChemSpider

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Desulfurilative self-coupling reaction of 1,3-thiazolidine-2-thiones and intramolecular non-bonded S?S interaction in the crystallographic structure of the products

An attempt at an asymmetric Pummerer-type reaction of trans-4-benzyloxythiane-1-oxide (1) with 3-trifluoroacetyl-4S-isopropyl-1,3-thiazolidine-2-thione (2) resulted in failure but an attractive desulfurilative self-coupling reaction of 4S-isopropyl-1,3-thiazolidine-2-thione (6) occurred to give 4S-isopropyl-3-(4S-isopropyl-1,3-thiazolin-2-yl)-1,3-thiazolidine-2-thione (5). The same desulfurilative self-coupling reaction of compound 6 or 11 efficiently proceeded by treatment of diphenyl sulfoxide (7a) or methyl phenyl sulfoxide (7b) with 2 or 3-trifluoroacetyl-1,3-thiazolidine-2-thione (8) to afford each corresponding product 5 or 9. Eventually, we found a practically useful method for the synthesis of 5 and 9 by exploiting TiCl4 and sodium salt 12 or 13 of 1,3-thiazolidine-2-thiones. Interestingly, intramolecular non-bonded S?S interactions were recognized in the crystallographic structures of 5 and 9.

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Quinuclidine | C7H748N | ChemSpider