A new practical method for the synthesis of unsymmetrical ureas via high-pressure-promoted condensation of 2,2,2-trichloroethyl carbamates (Troc-carbamates) with amines

Azad, Saleha; Kumamoto, Koji; Uegaki, Kaoru; Ichikawa, Yoshiyasu; Kotsuki, Hiyoshizo

doi:10.1016/j.tetlet.2005.11.045

Cited by 25 publications

(13 citation statements)

References 30 publications

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“…This suggests that the mechanism for this reaction is that methylamine nucleophilic attacks the isothiocyanate intermediate (yielded by the well-known base-promoted elimination of trichloroethanol) to produce the corresponding urea compounds (Azad et al, 2006). Review of previous literature, we found that the occurrence of this reaction required high pressure (Azad et al, 2006), high temperature (Jeong et al, 2016), or catalyst (Simard et al, 2009; Kono et al, 2013; Jang and Kim, 2017; Zhang et al, 2018) conditions. Accordingly, a new and more practical approach for the synthesis of ureido glycosides at room temperature and normal pressure without catalyst is reported here.…”

Section: Resultsmentioning

confidence: 99%

Design and Optimization of Thioglycosyl–naphthalimides as Efficient Inhibitors Against Human O-GlcNAcase

et al. 2019

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β-N-acetylhexosaminidases represent an important class of exoglycosidases and have emerged as the promising targets for drug and pesticide discovery. Among these, human O-GlcNAcase (hOGA) has been reported to be closely linked to several diseases such as Alzheimer's disease, diabetes, and cancer. Potent hOGA inhibitors with high selectivity are therefore of great significance for the regulation of the corresponding physiological processes. In this study, several classes of novel and readily available thioglycosyl-naphthalimides bearing the amide linker were designed and synthesized. To investigate their potency and selectivity, the inhibitory efficiencies toward hOGA and human β-N-acetylhexosaminidase B (HsHexB) were assayed. Especially, compounds 10a ( K i = 0.61 μM) and 16l ( K i = 0.72 μM) exhibited excellent inhibitory potency against hOGA and high selectivity (HsHexB, K i > 100 μM). In addition, during the preparation of these thioglycosyl–naphthalimides, a new practical method was developed for the synthesis of ureido glycosides from trichloroethyl carbamates at room temperature and normal pressure without catalyst. Furthermore, the possible binding modes of hOGA with 10a , 10d , and 16j were studied using molecular docking and molecular dynamics simulations to explore the molecular basis for the potency of these thioglycosides. This work present here provides useful clues for the further structural optimization toward hOGA.

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Section: Resultsmentioning

confidence: 99%

Design and Optimization of Thioglycosyl–naphthalimides as Efficient Inhibitors Against Human O-GlcNAcase

et al. 2019

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“…Less reactive carbamates require other means of activation. Urea synthesis from 2,2,2-trichloroethyl carbamates, for example, is achieved under high-pressure conditions, [70] and alkyl carbamates and amines yield ureas in the presence of 10 mol% zirconium(IV) tertbutoxide and 20 mol% 4-methyl-2-hydroxyquinoline. [71] Thermodynamic investigations addressing the reversibility of urea synthesis from 2,2,2-trifluoroethyl carbamates (see Section 18.8.22.1.1.7) reveal that the maximum expected yield for this reaction is 89%.…”

Section: Acyclic Unfunctionalized Ureasmentioning

confidence: 99%

Acyclic and Cyclic Ureas (Update 2013)

Banert¹,

Dobbs²,

Hall³

et al. 2013

Knowledge Updates 2013/3

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“…11) [45]. Sugar-derived ureas may also be formed by condensing amines with 2,2,2-trichloroethyl carbamates [46].…”

Section: N-glycosyl Ureas and Thioureasmentioning

confidence: 99%

Pyranose N-Glycosyl Amines: Emerging Targets With Diverse Biological Potential

Norris¹

2008

CTMC

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Interest in the chemistry and biological properties of non-nucleoside N-glycosidic compounds has gathered pace over the past several years; the occurrence of the N-glycoside moiety in glycoproteins and a range of active natural products has prompted the synthesis of a diverse spectrum of related materials with promising potential in medicinal chemistry. Particularly prominent has been the synthesis of novel N-glycosyl amides, 1,2,3-triazoles, and progress in the construction and diversification of natural products such as the mannopeptimycins and indolocarbazoles, each of which are discussed in this article.

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A new practical method for the synthesis of unsymmetrical ureas via high-pressure-promoted condensation of 2,2,2-trichloroethyl carbamates (Troc-carbamates) with amines

Cited by 25 publications

References 30 publications

Design and Optimization of Thioglycosyl–naphthalimides as Efficient Inhibitors Against Human O-GlcNAcase

Design and Optimization of Thioglycosyl–naphthalimides as Efficient Inhibitors Against Human O-GlcNAcase

Acyclic and Cyclic Ureas (Update 2013)

Pyranose N-Glycosyl Amines: Emerging Targets With Diverse Biological Potential

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