Vicinal diaryl azole-based urea derivatives as potential cholesterol lowering agents acting through inhibition of SOAT enzymes

Pal, Palash; Gandhi, Hardik; Kanhed, Ashish M.; Patel, Nirali R.; Mankadia, Niraj N.; Baldha, Satish N.; Barmade, Mahesh A.; Murumkar, Prashant R.; Yadav, Mange Ram

doi:10.1016/j.ejmech.2017.02.038

Cited by 11 publications

(3 citation statements)

References 60 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Substituted oxadiazoles attract attention because of their wide range of applications in organic synthesis as useful intermediates (Romeo & Chiacchio, 2011;Zlotin et al, 2017) and for drug design (Giorgis et al, 2011;Pal et al, 2017;Stepanov et al, 2015). In addition, molecules with the oxadiazole moiety can be considered for the creation of energetic systems (Zhang et al, 2015) with high thermal stability and mechanical sensitivity.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of poly[(μ₃-4-amino-1,2,5-oxadiazole-3-hydroxamato)thallium(I)]

et al. 2020

View full text Add to dashboard Cite

The title compound represents the thallium(I) salt of a substituted 1,2,5-oxadiazole, [Tl(C3H3N4O3)] n , with amino- and hydroxamate groups in the 4- and 3- positions of the oxadiazole ring, respectively. In the crystal, the deprotonated hydroxamate group represents an intermediate between the keto/enol tautomers and forms a five-membered chelate ring with the thallium(I) cation. The coordination sphere of the cation is augmented to a distorted disphenoid by two monodentately binding O atoms from two adjacent anions, leading to the formation of zigzag chains extending parallel to the b axis. The cohesion within the chains is supported by π–π stacking [centroid–centroid distance = 3.746 (3) Å] and intermolecular N—H...N hydrogen bonds.

show abstract

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of poly[(μ₃-4-amino-1,2,5-oxadiazole-3-hydroxamato)thallium(I)]

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Substituted urea can be exploited in a wide range of applications: as antioxidants in gasoline, agricultural chemicals, − dyes and intermediates, − additives in polymers synthesis, or thanks to their useful biological activities as structural components for drugs, HIV protease inhibitors, heme-regulated inhibitor kinase (HRI), CCK-B receptor, and endothelin antagonists, to name a few. − Moreover, their structures represent the skeleton of polymeric materials such as polyurea (PU) . Although PUs have been known for years in industry for their peculiar properties and high performance, huge efforts have been done in order to find new applications for these compounds.…”

Section: Introductionmentioning

confidence: 99%

Urea and Polyurea Production: An Innovative Solvent- and Catalyst-Free Approach through Catechol Carbonate

Soccio

Mazzoni

Lucarelli

et al. 2020

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

The peculiar reactivity of catechol carbonate (CC) with amines and polyamines in both solvent-and catalyst-free conditions is herein described. In all the tests performed at room temperature, CC conversion reached 100% in a few seconds leading to the selective formation of the corresponding 2hydroxyphenylcarbamate. This compound is further rapidly converted to the disubstituted urea by the consecutive nucleophilic attack of another amine. Noteworthy, the application of this approach can be successfully extended to the one-pot bioaminebased synthesis of polyurea as herein proposed for the first time in the literature. The reaction is of general purpose for primary amines, and catechol can be easily recovered by sublimation as pure crystals ready to be recycled for the synthesis of new CC. An exception is related to the reactivity of secondary amine, which leads to the selective formation of substituted phenolic carbamates (e.g., 2-hydroxyphenyl diethylcarbamate), suitable as intermediates in medicinal chemistry.

show abstract

“…Furazans (1,2,5-oxadiazoles, B , Figure ) constitute an important class of heterocycles that have found a myriad of applications in organic chemistry, in areas as disparate as the production of biologically active molecules and energetic materials . Although numerous methods for the preparation of furazans have been disclosed, the most straightforward approach involves the dehydrative cyclization of vicinal bisoximes ( A , Figure ).…”

mentioning

confidence: 99%

Mild Synthesis of Substituted 1,2,5-Oxadiazoles Using 1,1′-Carbonyldiimidazole as a Dehydrating Agent

Neel

Zhao

2018

Org. Lett.

View full text Add to dashboard Cite

1,1'-Carbonyldiimidazole was found to induce the formation of a variety of 3,4-disubstituted 1,2,5-oxadiazoles (furazans) from the corresponding bisoximes at ambient temperature. This method enables these inherently energetic compounds to be prepared at temperatures well below their decomposition points and with improved functional group compatibility relative to prior methods. Conditions were developed that allowed for the first high-yielding synthesis of chlorofurazans from their amino counterparts, enabling the mild synthetic manipulation of these heterocycles.

show abstract

Vicinal diaryl azole-based urea derivatives as potential cholesterol lowering agents acting through inhibition of SOAT enzymes

Cited by 11 publications

References 60 publications

Crystal structure of poly[(μ₃-4-amino-1,2,5-oxadiazole-3-hydroxamato)thallium(I)]

Crystal structure of poly[(μ₃-4-amino-1,2,5-oxadiazole-3-hydroxamato)thallium(I)]

Urea and Polyurea Production: An Innovative Solvent- and Catalyst-Free Approach through Catechol Carbonate

Mild Synthesis of Substituted 1,2,5-Oxadiazoles Using 1,1′-Carbonyldiimidazole as a Dehydrating Agent

Contact Info

Product

Resources

About

Vicinal diaryl azole-based urea derivatives as potential cholesterol lowering agents acting through inhibition of SOAT enzymes

Cited by 11 publications

References 60 publications

Crystal structure of poly[(μ3-4-amino-1,2,5-oxadiazole-3-hydroxamato)thallium(I)]

Crystal structure of poly[(μ3-4-amino-1,2,5-oxadiazole-3-hydroxamato)thallium(I)]

Urea and Polyurea Production: An Innovative Solvent- and Catalyst-Free Approach through Catechol Carbonate

Mild Synthesis of Substituted 1,2,5-Oxadiazoles Using 1,1′-Carbonyldiimidazole as a Dehydrating Agent

Contact Info

Product

Resources

About

Crystal structure of poly[(μ₃-4-amino-1,2,5-oxadiazole-3-hydroxamato)thallium(I)]

Crystal structure of poly[(μ₃-4-amino-1,2,5-oxadiazole-3-hydroxamato)thallium(I)]