75154-68-6Relevant academic research and scientific papers
Synthesis and Stability of the Cyclic Sulfamidate of N-Trityl-L-Serine Methyl Ester
Pilkington, Melanie,Wallis, John D.
, p. 1857 - 1858 (1993)
The title compound 12, prepared in three steps from L-serine methyl ester, is thermally stable 50 deg C; the formation of the cyclic sulfamidite 9, rather than acyclic products, in the reaction of thionyl chloride with vic-amino alcohol 7 is far more de
Structural Reassignment and Absolute Stereochemistry of Madurastatin C1 (MBJ-0034) and the Related Aziridine Siderophores: Madurastatins A1, B1, and MBJ-0035
Tyler, Andrew R.,Mosaei, Hamed,Morton, Stephanie,Waddell, Paul G.,Wills, Corinne,McFarlane, William,Gray, Joe,Goodfellow, Michael,Errington, Jeff,Allenby, Nick,Zenkin, Nikolay,Hall, Michael J.
, p. 1558 - 1562 (2017)
The madurastatins are pentapeptide siderophores originally described as containing an unusual salicylate-capped N-terminal aziridine ring. Isolation of madurastatin C1 (1) (also designated MBJ-0034), from Actinomadura sp. DEM31376 (itself isolated from a
Straightforward synthesis and antioxidant studies of chalcogenoaziridines
Borges, Rodrigo,Andrade, Floyd C.D.,Schwab, Ricardo S.,Sousa, Fernanda S.S.,de Souza, Maurice Neto,Savegnago, Lucielli,Schneider, Paulo H.
supporting information, p. 3501 - 3504 (2016/07/15)
Herein we reported the synthesis of chalcogenoaziridines through the introduction of the organoselenium moiety in the aziridine framework through the nucleophilic substitution of the OTs leaving group. In addition, the antioxidant activity, as reflected b
NOVEL COMPOUNDS
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, (2016/02/26)
A compound of formula (I) or a pharmaceutically acceptable derivative thereof, (formula 1) wherein R1,R2, R3, R4, R5, X, m and n are defined in the specification; a process for preparing such compounds; a pharmaceutical composition comprising such compounds; and the use of such compounds in medicine.
Total synthesis and activity of the metallo-β-lactamase inhibitor aspergillomarasmine A
Koteva, Kalinka,King, Andrew M.,Capretta, Alfredo,Wright, Gerard D.
supporting information, p. 2210 - 2212 (2016/02/19)
Resistance to β-lactam antibiotics is mediated primarily by enzymes that hydrolytically inactivate the drugs by one of two mechanisms: serine nucleophilic attack or metal-dependent activation of a water molecule. Serine β-lactamases are countered in the c
KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE
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Paragraph 0571; 0572, (2016/09/26)
Disclosed herein are new compounds and compositions and their application as pharmaceuticals for the treatment of diseases. Methods of inhibition of KDM1A, methods of increasing gamma globin gene expression, and methods to induce differentiation of cancer cells in a human or animal subject are also provided for the treatment of diseases such as acute myelogenous leukemia.
Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates
O'Brien, Keith,ó Proinsias, Keith,Kelleher, Fintan
supporting information, p. 5082 - 5092 (2014/07/08)
Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.
Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates
O'Brien, Keith,ó Proinsias, Keith,Kelleher, Fintan
supporting information, p. 5082 - 5092 (2014/12/10)
Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.
Synthesis of 1,2- trans -2-Acetamido-2-deoxyhomoiminosugars
Blriot, Yves,Tran, Anh Tuan,Prencipe, Giuseppe,Jagadeesh, Yerri,Auberger, Nicolas,Zhu, Sha,Gauthier, Charles,Zhang, Yongmin,Dsir, Jrme,Adachi, Isao,Kato, Atsushi,Sollogoub, Matthieu
, p. 5516 - 5519 (2015/02/19)
The first synthesis of 1,2-trans-homoiminosugars devised as mimics of I-d-GlcNAc and I-d-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a I-amino alcohol skeletal rearrangement applied to a polyhydroxylated azep
Proteomic searches comparing two (R)-lacosamide affinity baits: An electrophilic arylisothiocyanate and a photoactivated arylazide group
Park, Ki Duk,Stables, James P.,Liu, Rihe,Kohn, Harold
scheme or table, p. 2803 - 2813 (2010/08/21)
We have advanced a novel strategy to search for lacosamide ((R)-1) targets in the brain proteome where protein binding is expected to be modest. Our approach used lacosamide agents containing "affinity bait" (AB) and "chemical reporter" (CR) units. The affinity bait moiety is designed to irreversibly react with the target, and the CR group permits protein detection and capture. In this study, we report the preparation and evaluation of (R)-N-(4-azido)benzyl 2-acetamido-3-(prop-2-ynyloxy)propionamide ((R)-3) and show that this compound exhibits potent anticonvulsant activities in the MES seizure model in rodents. We compared the utility of (R)-3 with its isostere, (R)-N-(4-isothiocyanato)benzyl 2-acetamido-3-(prop-2-ynyloxy)propionamide ((R)-2), in proteomic studies designed to identify potential (R)-1 targets. We showed that despite the two-fold improved anticonvulsant activity of (R)-3 compared with (R)-2, (R)-2 was superior in revealing potential binding targets in the mouse brain soluble proteome. The difference in these agents' utility has been attributed to the reactivity of the affinity baits (i.e., (R)-2: aryl isothiocyanate moiety; (R)-3: photoactivated aryl azide intermediates) in the irreversible protein modification step, and we conclude that this factor is a critical determinant of successful target detection where ligand (drug) binding is modest. The utility of (R)-2 and (R)-3 in in situ proteome studies is explored.
