53181-99-0Relevant academic research and scientific papers
Catechol pendant polystyrene for solid-phase synthesis
Yang, Wenqian,Gao, Xingming,Springsteen, Greg,Wang, Binghe
, p. 6339 - 6342 (2002)
A catechol pendant polystyrene polymer was prepared from the Merrifield resin via a convenient procedure with high-density loading. Due to the high affinity binding between catechol and boronic acid, the polymer resin readily captures boronic acid compounds. The feasibility of using immobilized catechol to capture boronic acid products for purification and solid-phase transformation was demonstrated. Moreover, the immobilized catechol was also used for the preparation of resin-bound catecholborane, which can be used as a solid-phase amidation reagent.
Volatiles from the Psychrotolerant Bacterium Chryseobacterium polytrichastri
Lauterbach, Lukas,Dickschat, Jeroen S.
, p. 3608 - 3617 (2020/09/22)
The flavobacterium Chryseobacterium polytrichastri was investigated for its volatile profile by use of a closed-loop stripping apparatus (CLSA) and subsequent GC-MS analysis. The analyses revealed a rich headspace extract with 71 identified compounds. Compound identification was based on a comparison to library mass spectra for known compounds and on a synthesis of authentic standards for unknowns. Important classes were phenylethyl amides and a series of corresponding imines and pyrroles.
Antagonism of quorum sensing phenotypes by analogs of the marine bacterial secondary metabolite 3-methyl-N-(20-phenylethyl)-butyramide
Meschwitz, Susan M.,Teasdale, Margaret E.,Mozzer, Ann,Martin, Nicole,Liu, Jiayuan,Forschner-Dancause, Stephanie,Rowley, David C.
, (2019/07/15)
Quorum sensing (QS) antagonists have been proposed as novel therapeutic agents to combat bacterial infections. We previously reported that the secondary metabolite 3-methyl-N-(20-phenylethyl)-butyramide, produced by a marine bacterium identifie
Biocatalytic N-Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis
Contente, Martina Letizia,Pinto, Andrea,Molinari, Francesco,Paradisi, Francesca
, p. 4814 - 4819 (2018/11/10)
A straightforward one-step biocatalyzed synthesis of different N-acyl amides in water was accomplished using the versatile and chemoselective acyltransferase from Mycobacterium smegmatis (MsAcT). Acetylation of primary arylalkyl amines was achieved with a range of acetyl donors in biphasic systems within 1 hour and at room temperature. Vinyl acetate was the best donor which could be employed in the N-acetylation of a large range of primary amines in excellent yields (85–99%) after just 20 minutes. Other acyl donors (including formyl-, propionyl-, and butyryl-donors) were also efficiently employed in the biocatalytic N-acylation. Finally, the biocatalyst was tested in transamidation reactions using acetamide as acetyl donor in aqueous medium, reaching yields of 60–70%. This work expands the toolbox of preparative methods for the formation of N-acyl amides, describing a biocatalytic approach easy to accomplish under mild conditions in water. (Figure presented.).
Facile direct synthesis of amides from trichloroethyl esters using catalytic DBU
La, Minh Thanh,Kim, Hee-Kwon
, p. 1135 - 1141 (2018/11/25)
A practical method for the direct synthesis of amide compounds is described. Using small quantities of DBU as a catalyst, the direct conversion of 2,2,2-trichloroethyl esters to their corresponding amides was readily achieved. Based on this protocol, various amide compounds were successfully synthesized in high yield, suggesting a promising approach for the practical one-pot aminolysis from 2,2,2-trichloroethyl protected esters.
Virtual screening for novel Atg5-Atg16 complex inhibitors for autophagy modulation
Robinson, Elizabeth,Leung, Euphemia,Matuszek, Anna M.,Krogsgaard-Larsen, Niels,Furkert, Daniel P.,Brimble, Margaret A.,Richardson, Alan,Reynisson, Jhannes
supporting information, p. 239 - 246 (2015/02/02)
Two hit compounds (14 and 62) were identified using virtual high throughput screening (vHTS) inhibiting the autophagy process in A2780 ovarian cancer cells. The expression levels of the LC3-II and p62 autophagy marker proteins were monitored using Western blotting. Preliminary structure activity relationship (SAR) study of close structural analogues revealed another active compound 38. The three active compounds were tested in the MCF-7 human breast cancer cells and severe reduction of autophagosomes formation was observed confirming the activity of the inhibitors. The docking scaffold used for the vHTS was a lipophilic cleft on the Atg5 protein, which is occupied by a phenylalanine residue in the Atg16 polypeptide. To the best of our knowledge this is the first report on inhibitors that specifically modulate autophagy by directly inhibiting autophagy specific proteins, which is significant due the role autophagy plays in a number of morbid diseases such as cancer. This journal is
Inhibition of the production of the Pseudomonas aeruginosa virulence factor pyocyanin in wild-type cells by quorum sensing autoinducer-mimics
Morkunas, Bernardas,Galloway, Warren R. J. D.,Wright, Megan,Ibbeson, Brett M.,Hodgkinson, James T.,O'Connell, Kieron M. G.,Bartolucci, Noemi,Valle, Martina Della,Welch, Martin,Spring, David R.
, p. 8452 - 8464 (2013/01/15)
Pseudomonas aeruginosa is a notorious human pathogen associated with a range of life-threatening nosocomial infections. There is an increasing problem of antibiotic resistance in P. aeruginosa, highlighted by the emergence of multi-drug resistant strains.
Amidation of aldehydes and alcohols through α-iminonitriles and a sequential oxidative three-component strecker reaction/thio-michael addition/alumina-promoted hydrolysis process to access β-mercaptoamides from aldehydes, amines, and thiols
Gualtierotti, Jean-Baptiste,Schumacher, Xavier,Fontaine, Patrice,Masson, Géraldine,Wang, Qian,Zhu, Jieping
, p. 14812 - 14819 (2013/01/15)
Mild and general alumina-promoted hydrolysis conditions for converting α-iminonitriles into carboxamides have been developed. In combination with the oxidative three-component Strecker reaction, the one-pot direct amidation of aldehydes and alcohols is reported. Subsequently, an Yb(OTf) 3-catalyzed Michael addition of thiols to α,β-unsaturated α-iminonitriles is reported for the synthesis of β-mercapto-α- iminonitriles. The successful integration of an oxidative Strecker reaction, thio-Michael addition, and neutral-alumina-promoted hydrolysis of β-mercapto-α-iminonitriles into a three-component one-pot process allowed us to develop the direct conversion of amines, aldehydes, and thiols into β-mercaptoamides. All of these procedures were applicable to aromatic and aliphatic amines and aldehydes. First direct: The direct amidation reactions of aldehydes and alcohols were performed in combination with the oxidative three-component synthesis of α-iminonitriles. In addition, β-mercaptoamides were readily accessed from α,β-unsaturated aldehydes, amines, and thiols by a sequential process that involved a three-component Strecker reaction, Yb(OTf)3-catalyzed thio-Michael addition, and hydrolysis of the resulting β-mercapto-α-iminonitriles (see scheme). Copyright
Phencyclidine-like Effects of Tetrahydroisoquinolines and Related Compounds
Gray, Nancy M.,Cheng, Brian K.,Mick, Stephen J.,Lair, Cecelia M.,Contreras, Patricia C.
, p. 1242 - 1248 (2007/10/02)
A series of 1,2,3,4-tetrahydroisoquinolines, tetrahydrothienopyridines, and related compounds were evaluated for their ability to inhibit binding of -1--N-allylnormetazocine to phencyclidine (PCP) and ? receptors, respectively.A representative series of compounds was evaluated in behavioral assays to determine the ability of the compounds to induce PCP-like stereotyped behavior and ataxia.All of the compounds caused stereotyped behavior and ataxia, indicating their agonist actions at the PCP site.
