- Di-tert-butyl peroxide (DTBP)-mediated synthesis of symmetrical N,N′-disubstituted urea/thiourea motifs from isothiocyanates in water
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ABATRACT: A direct approach to N,N′-disubstituted urea/thiourea from the self-condensation reactions of isothiocyanates in water has been developed. This access tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to N,N′-disubstituted urea/thiourea in moderate to excellent yields from safe and easily available starting materials. A plausible mechanism of the desulfurization self-condensation reaction for urea was also proposed and the role of di-tert-butyl peroxide (DTBP) and copper catalyst in the present strategy was demonstrated with the help of ESI mass spectrometry of intermediate studies.
- Chen, Ling,Dong, Yibo,Wu, Yangjie,Yang, Jinchen,Zhang, Jinli
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supporting information
(2021/12/01)
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- Identification of organophosphorus simulants for the development of next-generation detection technologies
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Organophosphorus (OP) chemical warfare agents (CWAs) represent an ongoing threat but the understandable widespread prohibition of their use places limitations on the development of technologies to counter the effects of any OP CWA release. Herein, we describe new, accessible methods for the identification of appropriate molecular simulants to mimic the hydrogen bond accepting capacity of the PO moiety, common to every member of this class of CWAs. Using the predictive methodologies developed herein, we have identified OP CWA hydrogen bond acceptor simulants for soman and sarin. It is hoped that the effective use of these physical property specific simulants will aid future countermeasure developments.
- Ellaby, Rebecca J.,Clark, Ewan R.,Allen, Nyasha,Taylor, Faith R.,Ng, Kendrick K. L.,Dimitrovski, Milan,Chu, Dominique F.,Mulvihill, Daniel P.,Hiscock, Jennifer R.
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p. 2008 - 2014
(2021/03/16)
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- Design, synthesis, and biological evaluation of novel substituted thiourea derivatives as potential anticancer agents for NSCLC by blocking K-Ras protein-effectors interactions
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Mutation of the proto-oncogene K-Ras is one of the most common molecular mechanisms in non-small cell lung cancer. Many drugs for treating lung cancer have been developed, however, due to clinical observed K-Ras mutations, corresponding chemotherapy and targeted therapy for such mutation are not efficient enough. In this study, on the basis of the crystal structure of K-Ras, 21 analogues (TKR01–TKR21) containing urea or thiourea were rationally designed, which can effectively inhibit the lung cancer cell A549 growth. The designing of these compounds was based on the structure of K-Ras protein, and the related groups were replaced by bioisosteres to improve the affinity and selectivity. Biological testing revealed that compound TKR15 could significantly inhibit the proliferation of A549 cell with IC50 of 0.21 μM. Docking analysis showed that the TKR15 can effectively bind to the hydrophobic cavity and form a hydrogen bond with the Glu37. In addition, through flow apoptosis assay and immunofluorescence staining assay, it confirmed that this compound can inhibit A549 cell proliferation with the mechanism of blocking K-RasG12V protein and effector proteins interactions through the apoptotic pathway. In conclusion, our studies in finding novel potent compound (TKR15) with confirmed mechanism showed great potential for further optimisation and other medicinal chemistry relevant studies.
- Cheng, Minghui,Meng, Xin,Tang, Haikang,Xu, Wenqing,Yang, Fujun,Zhang, Yuan
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p. 344 - 353
(2019/12/30)
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- Compound comprising urea and thiourea structures and synthesis method and application of compound
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The invention relates to an organic small molecular compound comprising urea and thiourea structures in a formula I and a synthesis method and application of the compound. According to in-vitro antitumor activity tests, the compound has high antitumor act
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- Nickle Catalysis Enables Access to Thiazolidines from Thioureas via Oxidative Double Isocyanide Insertion Reactions
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An efficient synthesis of thiazolidine-2,4,5-triimine derivatives was developed via Ni-catalyzed oxidative double isocyanide insertion to thioureas under air conditions, in which thioureas play three roles as a substrate, a ligand, and overcoming isocyanide polymerization. The reaction is featured by employing a low-cost and low loading Ni(acac)2 catalyst, without any additives, and high atom economy. This is the first example to directly apply a Ni(II) catalyst in oxidative double isocyanide insertion reactions.
- Yuan, Wen-Kui,Liu, Yan Fang,Lan, Zhenggang,Wen, Li-Rong,Li, Ming
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supporting information
p. 7158 - 7162
(2018/11/25)
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- CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.
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Paragraph 000703; 000704; 000901; 000902
(2018/01/17)
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- Squaramides as potent transmembrane anion transporters
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Square peg in a round ball: Squaramides are shown to be potent transmembrane anion transporters for both chloride and bicarbonate, performing better than the thiourea and urea analogues. Studies into the nature of this transport point to a mobile carrier mechanism, where the squaramide delivers the anion cargo across the lipid bilayer (see scheme, green sphere=anion). These drug-like molecules provide a platform for the development of a new generation of anion-transport systems. Copyright
- Busschaert, Nathalie,Kirby, Isabelle L.,Young, Sarah,Coles, Simon J.,Horton, Peter N.,Light, Mark E.,Gale, Philip A.
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supporting information; experimental part
p. 4426 - 4430
(2012/06/04)
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- Desulfurization strategy in the construction of azoles possessing additional nitrogen, oxygen or sulfur using a copper(I) catalyst
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A tandem and convergent approach to various N-, O-, or S-containing azoles has been developed by exploiting the thiophilic property of copper( I) iodide used in a catalytic quantity. The present protocol gives access to amino-substituted tetrazoles, triazoles, oxadiazoles and thiadiazoles via oxidative desulfurization of their respective precursors followed by inter- or intramolecular attack of suitable nucleophiles. For aminotetrazoles and triazoles an excellent regioselectivity has been achieved through proper tuning of the pKa values of the parent amines attached to unsymmetrical thioureas. The method represents an autocatalytic process in which copper( I) iodide gets converted to copper(II) sulfide which in turn transforms to active copper(II) oxide that effectively carries forward the catalytic cycle. The fate of the copper catalyst has also been studied using scanning electron microscopic (SEM) and energy-dispersive X-ray spectroscopic (EDS) analyses which give an insight into the mechanism for this catalytic process.
- Guin, Srimanta,Rout, Saroj Kumar,Gogoi, Anupal,Nandi, Shyamapada,Ghara, Krishna Kanta,Patel, Bhisma K.
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p. 2757 - 2770
(2013/01/15)
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