- P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids
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An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.
- Meng, Haiwen,Sun, Kunhui,Xu, Zhimin,Tian, Lifang,Wang, Yahui
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supporting information
p. 1768 - 1772
(2021/03/26)
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- An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives
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An operationally simple, and cost efficient conversion of carboxylic acids into hydroxamic acid derivatives via a high-energy mechanochemical activation is presented. This ball milling methodology was applied to a wide variety of carboxylic acids dramatically improving purification issues associated with this class of molecules, which still remain one of the main bottlenecks of classical methodologies. (Figure presented.).
- Mocci, Rita,De Luca, Lidia,Delogu, Francesco,Porcheddu, Andrea
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supporting information
p. 3135 - 3144
(2016/10/09)
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- One-pot synthesis of primary amines from carboxylic acids through rearrangement of in situ generated hydroxamic acid derivatives
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A one-pot synthesis of primary amines from carboxylic acids through a Lossen rearrangement of hydroxamic acid derivatives, which were in situ generated by the reaction of carboxylic acids with O-trimethylsilylhydroxylamine (NH2OTMS) and carbonyl diimidazole (CDI, 1.5 equiv) in dimethyl sulfoxide at room temperature, has been achieved. This one-pot method could be applied to various carboxylic acids such as aromatic, heteroaromatic, aliphatic, and optically active substrates.
- Hoshino, Yujiro,Ohtsuka, Naoya,Okada, Takuya,Honda, Kiyoshi
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supporting information
p. 5304 - 5307
(2016/11/16)
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- N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement
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An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.
- Yoganathan, Sabesan,Miller, Scott J.
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supporting information
p. 602 - 605
(2013/04/11)
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- Carbonyldiimidazole-mediated lossen rearrangement
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[Chemical Equation Presented] Carbonyldiimidazole (CDI) was found to mediate the Lossen rearrangement of various hydroxamic acids to isocyanates. This process is experimentally simple and mild, with imidazole and CO 2 being the sole stoichiometric byproduct. Significant for large-scale application, the method avoids the use of hazardous reagents and thus represents a green alternative to standard processing conditions for the Curtius and Hofmann rearrangements.
- Dube, Pascal,Fine Nathel, Noah F.,Vetelino, Michael,Couturier, Michel,Aboussafy, Claude Larrivee,Pichette, Simon,Jorgensen, Matthew L.,Hardink, Mark
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supporting information; body text
p. 5622 - 5625
(2010/03/02)
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- INHIBITORS OF HISTONE DEACETYLASE
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This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula compounds of the Formula (I) and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof, and racemic and scalemic mixtures, diastereomers and enantiomers thereof, wherein groups L, M, X and Y are as defined herein.
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Page/Page column 56
(2008/12/04)
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- INHIBITORS FOR HDAC8
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INHIBITORS FOR HDAC8 ABSTRACT OF THE DISCLOSURE This invention discloses a new HDAC inhibitor scaffold designed to exploit a unique sub-pocket of the HDAC8 active site. These compounds are based on inspection of HDAC8 crystal structures bound to various inhibitors, which showed that the HDAC8 active site is surprisingly malleable and can accommodate inhibitor structures that are distinct from the canonical "zinc-binding group-linker-cap group" structures of SAHA, TSA and similar HDAC inhibitors. Some of the new inhibitors based on this new scaffold are >100 fold selective for HDAC8 over other class I and class II HDACs with IC50 values 1μM against HDAC8. The present invention provides a new type of "linkerless" HDAC8 inhibitors and methods of treating a pathological condition using the same. Treatment of human cells with the new inhibitors of the present invention show a unique pattern of hyperacetylated proteins compared with the broad spectrum HDAC inhibitor TSA.
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Page/Page column 81
(2008/12/08)
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- Design and evaluation of 'Linkerless' hydroxamic acids as selective HDAC8 inhibitors
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In this report, we describe new HDAC inhibitors designed to exploit a unique sub-pocket in the HDAC8 active site. These compounds were based on inspection of the available HDAC8 crystal structures bound to various inhibitors, which collectively show that the HDAC8 active site is unusually malleable and can accommodate inhibitor structures that are distinct from the canonical 'zinc binding group-linker-cap group' structures of SAHA, TSA, and similar HDAC inhibitors. Some inhibitors based on this new scaffold are >100-fold selective for HDAC8 over other class I and class II HDACs with IC50 values 1 μM against HDAC8. Furthermore, treatment of human cells with the inhibitors described here shows a unique pattern of hyperacetylated proteins compared with the broad-spectrum HDAC inhibitor TSA.
- KrennHrubec, Keris,Marshall, Brett L.,Hedglin, Mark,Verdin, Eric,Ulrich, Scott M.
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p. 2874 - 2878
(2008/02/03)
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- Identification of a potent botulinum neurotoxin A protease inhibitor using in situ lead identification chemistry
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Botulinum neurotoxins (BoNTs), etiological agents of the deadly food poisoning disease botulism, are the most toxic proteins currently known. By using in situ lead identification chemistry, we have uncovered the first class of inhibitors that displays nanomolar potency. From a 15 μM lead compound, structure-activity relationship studies were performed granting the most potent BoNT/A inhibitor reported to date that displays an inhibition constant of 300 nM.
- Boldt, Grant E.,Kennedy, Jack P.,Janda, Kim D.
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p. 1729 - 1732
(2007/10/03)
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- A FACILE PREPARATION OF ALIPHATIC HYDROXAMIC ACID FROM N,N,O-TRIS(TRIMETHYLSILYL)HYDROXYLAMINE AND ACID CHLORIDE
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N,N,O-Tris(trimethylsilyl)hydroxylamine reacts readily with various aliphatic acid chlorides under mild conditions to afford the corresponding hydroxamic acids in good yields.
- Ando, Wataru,Tsumaki, Hidetoshi
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p. 1053 - 1056
(2007/10/02)
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- Potentiometric Determination of Formation Constants of Metal Chelates Involving Some Rare Earth Metal Ions and 2,2'-Diphenylacetohydroxamic Acid
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Metal-ligand stability constants of complexes of Dy(III), Sm(III), Nd(III), Pr(III) and Gd(III) with 2,2'-diphenylacetohydroxamic acid have been determined potentiometrically at different temperatures (μ = 0.1 M KNO3) and at different ionic strengths (tem
- Subba Reddy, V. V.,Sethuram, B.,Navaneeth Rao, T.
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p. 1140 - 1142
(2007/10/02)
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