57913-41-4Relevant articles and documents
Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation
Chang, Sukbok,Jung, Hoimin,Keum, Hyeyun,Kweon, Jeonguk
supporting information, p. 5811 - 5818 (2020/04/10)
Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.
Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions
Chang, Sukbok,Jung, Hoimin,Kim, Dongwook,Lee, Jeonghyo,Lee, Jia,Park, Juhyeon
supporting information, p. 12324 - 12332 (2020/08/06)
Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.
Specificity of extended O-aryloxycarbonyl hydroxamates as inhibitors of a class C β-lactamase
Malico, Alexandra A.,Dave,Adediran,Pratt
, p. 1430 - 1436 (2019/02/24)
Class C β-lactamases have previously been shown to be efficiently inactivated by O-aryloxycarbonyl hydroxamates. O-Phenoxycarbonyl-N-benzyloxycarbonylhydroxylamine (1) and O-phenoxycarbonyl-N-(R)-[(4-amino-4-carboxy-1-butyl)oxycarbonyl]hydroxylamine (2),
Design and Comparative Evaluation of the Anticonvulsant Profile, Carbonic-Anhydrate Inhibition and Teratogenicity of Novel Carbamate Derivatives of Branched Aliphatic Carboxylic Acids with 4-Aminobenzensulfonamide
Bibi, David,Mawasi, Hafiz,Nocentini, Alessio,Supuran, Claudiu T.,Wlodarczyk, Bogdan,Finnell, Richard H.,Bialer, Meir
, p. 1972 - 1982 (2017/07/17)
Epilepsy is one of the most common neurological diseases, with between 34 and 76 per 100,000 people developing epilepsy annually. Epilepsy therapy for the past 100+ years is based on the use of antiepileptic drugs (AEDs). Despite the availability of more than twenty old and new AEDs, approximately 30% of patients with epilepsy are not seizure-free with the existing medications. In addition, the clinical use of the existing AEDs is restricted by their side-effects, including the teratogenicity associated with valproic acid that restricts its use in women of child-bearing age. Thus, there is an unmet clinical need to develop new, effective AEDs. In the present study, a novel class of carbamates incorporating phenethyl or branched aliphatic chains with 6–9 carbons in their side-chain, and 4-benzenesulfonamide-carbamate moieties were synthesized and evaluated for their anticonvulsant activity, teratogenicity and carbonic anhydrase (CA) inhibition. Three of the ten newly synthesized carbamates showed anticonvulsant activity in the maximal-electroshock (MES) and 6?Hz tests in rodents. In mice, 3-methyl-2-propylpentyl(4-sulfamoylphenyl)carbamate(1), 3-methyl-pentan-2-yl-(4-sulfamoylphenyl)carbamate (9) and 3-methylpentyl, (4-sulfamoylphenyl)carbamate (10) had ED50 values of 136, 31 and 14?mg/kg (MES) and 74, 53, and 80?mg/kg (6?Hz), respectively. Compound (10) had rat-MES-ED50 = 13?mg/kg and ED50 of 59?mg/kg at the mouse-corneal-kindling test. These potent carbamates (1,9,10) induced neural tube defects only at doses markedly exceeding their anticonvuslnat-ED50 values. None of these compounds were potent inhibitors of CA IV, but inhibited CA isoforms I, II and VII. The anticonvulsant properties of these compounds and particularly compound 10 make them potential candidates for further evaluation and development as new AEDs.
The grunwald-winstein relationship in the solvolysis of β-substituted chloroformate ester derivatives: The solvolysis of 2-phenylethyl and 2,2-diphenylethyl chloroformates
Park, Kyoung-Ho,Yang, Gi-Hoon,Kyong, Jin Burm
, p. 2263 - 2270 (2014/12/10)
Solvolysis rate constants of 2-phenylethyl-(2-PhCH2CH 2OCOCl, 1) and 2,2-diphenylethyl chloroformate (2,2- Ph2CHCH 2OCOCl, 2), together with the previously studied solvolyses of α- and β-substituted chloroformate ester der
Exploration of the P2-P3 SAR of aldehyde cathepsin K inhibitors
Boros, Eric E.,Deaton, David N.,Hassell, Anne M.,McFadyen, Robert B.,Miller, Aaron B.,Miller, Larry R.,Paulick, Margot G.,Shewchuk, Lisa M.,Thompson, James B.,Willard Jr., Derril H.,Wright, Lois L.
, p. 3425 - 3429 (2007/10/03)
The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S2 and S3 subsites with a series of carbamate derivatized norleucine aldehydes substituted at the P2 and P3 positions afforded analogs with cathepsin K IC50s between 600nM and 130pM.
Dipeptidyl aspartyl fluoromethylketones as potent caspase inhibitors: SAR of the N-protecting group
Cai, Sui Xiong,Guan, Lufeng,Jia, Shaojuan,Wang, Yan,Yang, Wu,Tseng, Ben,Drewe, John
, p. 5295 - 5300 (2007/10/03)
The synthesis and biological evaluation of a group of N-protected Val-Asp-fmk as caspase inhibitors is reported. This article describes the synthesis and biological evaluation of a group of N-protected Val-Asp-fmk as caspase inhibitors. The protecting group was found to contribute to caspase-3 inhibiting activity, and compounds with a large group such as Cbz are more active than compounds with a small group such as Ac. Compounds with more hydrophobic protecting groups were found to be more active in cell apoptosis protection assays, probably due to increased cell permeability. MX1122, 2,4-di-Cl-Cbz-Val-Asp-fmk, is identified as a potent broad-spectrum caspase inhibitor and is selective for caspases versus other proteases, with good activity in the cell apoptosis protection assays as well as good efficacy in the mouse liver apoptosis model.
Functionalization of single-walled carbon nanotubes with (R-)oxycarbonyl nitrenes
Holzinger, Michael,Abraham, Juergen,Whelan, Paul,Graupner, Ralf,Ley, Lothar,Hennrich, Frank,Kappes, Manfred,Hirsch, Andreas
, p. 8566 - 8580 (2007/10/03)
Sidewall functionalization of single-walled carbon nanotubes (SWCNTs) via the addition of (R-)-oxycarbonyl nitrenes allows for the covalent binding of a variety of different groups such as alkyl chains, aromatic groups, dendrimers, crown ethers, and oligoethylene glycol units. Such additions lead to a considerable increase in the solubility in organic solvents such as 1,1,2,2-tetrachloroethane (TCE), dimethyl sulfoxide (DMSO), and 1,2-dichlorobenzene (ODCB). The highest solubilities of 1.2 mg/mL were found for SWCNT adducts with nitrenes containing crown ether of oligoethylene glycol moieties in DMSO and TCE, respectively. The presence of chelating donor groups within the addends allowed for the complexation of Cu2+ and Cd2+. Atomic force microscopy (AFM) and transmission electron microscopy (TEM) revealed that the functionalized tubes form thin bundles with typical diameters of 10 nm. The presence of thin bundles in solution is supported by 1H NMR spectroscopy. The elemental composition of the functionalized SWCNT was determined by X-ray photoelectron spectroscopy (XPS). The use of Raman and electron absorption spectroscopy (UV/Vis-nIR) showed that the electronic properties of the SWCNTs are mostly retained after functionalization, indicating a low degree of addition within this series of SWCNT derivatives.
Synthesis, hydrolysis, biochemical and theoretical evaluation of 1,4-bis(alkoxycarbonyl)azetidin-2-ones as potential elastase inhibitors
Gérard, Stéphane,Dive, Georges,Clamot, Brigitte,Touillaux, Roland,Marchand-Brynaert, Jacqueline
, p. 2423 - 2433 (2007/10/03)
A series of 1,4-bis(alkoxycarbonyl)azetidin-2-ones, designed as potential suicide-inhibitors of serine proteases, has been synthesized and evaluated against porcine pancreatic elastase (PPE). The most active compound (Ki～10 μM; reversible inhibitor) was equipped with phenethyloxycarbonyl and benzyloxycarbonyl side-chains at positions N1 and C4, respectively, with the (S)-configuration. 1H NMR spectroscopic analysis of the reaction mixtures showed that the ester function is preferentially hydrolyzed, in both chemical and enzyme-catalyzed reactions, with regard to the azetidinone and urethane functions. Considering the three potentially sensitive carbonyl functions and the two stereoisomers, ab initio calculations were performed to determine the energetic barriers required to reach the transition state structures of hydrolysis in a model of the enzyme pocket.
Synthesis of 5-membered ring-type compounds as potential cholecystokinin receptor ligands
Pentassuglia,Luca Araldi,Donati,Feriani,Oliosi,Pasquarello,Ursini
, p. 573 - 581 (2007/10/03)
Imidazolidine-2,4-diones and 1,5-diphenyl tetrainic acid derivatives were selected in order to evaluate some 5-membered heterocyclic ring compounds as potential templates for the synthesis of CCK receptor ligands. All the compounds were evaluated in vitro towards both CCK-B and CCK-A receptors.
