Synthesis of 5-arylated N-arylthiazole-2-amines as potential skeletal muscle cell differentiation promoters

Schnürch, Michael; Waldner, Birgit J.; Hilber, Karlheinz; Mihovilovic, Marko D.

doi:10.1016/j.bmcl.2011.01.123

Cited by 23 publications

(16 citation statements)

References 66 publications

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“…One such approach is the inclusion of drugs into cyclodextrins, macromolecules that can form inclusion complexes (ICs) modifying the physical, chemical, and/or biological properties of the included drug [ 3 – 6 ]. The most commonly used is the βcyclodextrin (βCD), which has applications in pharmaceuticals, food stuffs, and environmental protection, among many others [ 7 – 10 ]. Specifically, βCD is a water soluble, nontoxic cyclic oligosaccharide conformed of 7 glucopyranose units ( Fig 1A ) observable as a three-dimensional bucket-like shape, with primary hydroxyl groups in the narrowest extreme and secondary hydroxyls groups in the widest extreme.…”

Section: Introductionmentioning

confidence: 99%

Gold nanoparticles stabilized with βcyclodextrin-2-amino-4-(4-chlorophenyl)thiazole complex: A novel system for drug transport

et al. 2017

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While 2-amino-4-(4-chlorophenyl)thiazole (AT) drug and thiazole derivatives have several biological applications, these compounds present some drawbacks, such as low aqueous solubility and instability. A new complex of βCD-AT has been synthesized to increase AT solubility and has been used as a substrate for the deposit of solid-state AuNPs via magnetron sputtering, thus forming the βCD-AT-AuNPs ternary system, which is stable in solution. Complex formation has been confirmed through powder X-ray diffraction and 1D and 2D nuclear magnetic resonance. Importantly, the amine and sulfide groups of AT remained exposed and can interact with the surfaces of the AuNPs. The complex association constant (970 M-1) has been determined using phase solubility analysis. AuNPs formation (32 nm average diameter) has been studied by UV-Visible spectroscopy, transmission/scanning electron microscopy and energy-dispersive X-ray analysis. The in vitro permeability assays show that effective permeability of AT increased using βCD. In contrast, the ternary system did not have the capacity to diffuse through the membrane. Nevertheless, the antibacterial assays have demonstrated that AT is transferred from βCD-AT-AuNPs, being available to exert its antibacterial activity. In conclusion, this novel βCD-AT-AuNPs ternary system is a promising alternative to improve the delivery of AT drugs in therapy.

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Section: Introductionmentioning

confidence: 99%

Gold nanoparticles stabilized with βcyclodextrin-2-amino-4-(4-chlorophenyl)thiazole complex: A novel system for drug transport

et al. 2017

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“…We started our investigations by using the reaction conditions that we recently introduced for the successful C-5 arylation of N -protected thiazoleamines. [ 18 ] There we used palladium acetate [Pd(OAc) 2 ] as catalyst without an additional ligand, potassium acetate (KOAc) as base and N , N -dimethylacetamide (DMAc) as solvent at 140 °C for 24 h. In the case of the arylation of thiazole, aryl iodides served as the aryl source, whereas for the arylation of benzo[ b ]furan we wanted to focus on cheaper and more readily available bromides. As a model reaction we investigated the coupling of 4-bromoanisole with benzo[ b ]furan.…”

Section: Resultsmentioning

confidence: 99%

Direct Arylation of Benzo[b]furan and Other Benzo‐Fused Heterocycles

et al. 2014

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The direct arylation of benzo[b]furan, benzo[b]thiophene, and indole has been studied by using aromatic bromides as the aryl source. The protocol employing common reagents and a Pd catalyst has led to the regioselective arylation of these heterocycles at the 2-position. A range of functional groups were tolerated, providing quick access to a variety of arylated benzo-fused heterocycles that would be accessible more elaborately using classical synthetic strategies. This is the first systematic study of the direct arylation of benzo[b]furan.

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“…Direct arylation of thiazole-2-amines towards cell differentiation accelerators. 44 Besides method development in C-H activation chemistry we also aim to apply these methods in the synthesis of functional molecules. We had identified a compound class which showed interesting activity in the field of cell differentiation modulators.…”

Section: Methodsmentioning

confidence: 99%

Exploiting the C-H bond in metal catalyzed C-C bond forming reactions

Schnürch¹

2015

Arkivoc

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This account summarizes our work in the field of direct C-H bond functionalization. We have explored methods in the area of directing group assisted C(sp 2 )-H and C(sp 3 )-H activation and investigated arylation as well as deuteration reactions. In these transformations either ruthenium or palladium catalysts were applied. In case of C(sp 2 )-H activation, we developed a protocol for the synthesis of ortho arylated anilines and disclosed the first method for a direct arylation in a continuous flow reactor. Additionally, we applied a direct arylation in the synthesis of compounds which can accelerate cell differentiation. In the field of C(sp 3 )-H activation we developed a protocol for the selective mono-arylation of piperidine and three different arylation protocols for acyclic amines employing either aryl chlorides, aryl bromides, aryl iodides, or arylboronic acid esters as the aryl donor.

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Synthesis of 5-arylated N-arylthiazole-2-amines as potential skeletal muscle cell differentiation promoters

Cited by 23 publications

References 66 publications

Gold nanoparticles stabilized with βcyclodextrin-2-amino-4-(4-chlorophenyl)thiazole complex: A novel system for drug transport

Gold nanoparticles stabilized with βcyclodextrin-2-amino-4-(4-chlorophenyl)thiazole complex: A novel system for drug transport

Direct Arylation of Benzo[b]furan and Other Benzo‐Fused Heterocycles

Exploiting the C-H bond in metal catalyzed C-C bond forming reactions

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