53731-88-7Relevant academic research and scientific papers
Investigation of the dynamic nature of 1,2-oxazines derived from peralkylcyclopentadiene and nitrosocarbonyl species
Kensy, Victoria K.,Peterson, Gregory I.,Church, Derek C.,Yakelis, Neal A.,Boydston, Andrew J.
, p. 5617 - 5621 (2016)
We have investigated the reversible hetero-Diels-Alder reaction of 1,2-oxazines derived from a peralkylcyclopentadiene and a series of nitrosocarbonyl dienophiles. The nature of the dienophile was found to impart broad tunability to the dynamic character of the oxazine adducts. The reversibility was also observed in polymeric systems. The fidelity of the reaction and tunable sensitivity toward elevated temperature and water signify potential applications in the development of dynamic covalent materials or delivery systems for small molecule payloads.
Photoinduced upregulation of calcitonin gene-related peptide in A549 cells through HNO release from a hydrophilic photocontrollable HNO donor
Matsuo, Kazuya,Nakagawa, Hidehiko,Adachi, Yusuke,Kameda, Eri,Aizawa, Kazuyuki,Tsumoto, Hiroki,Suzuki, Takayoshi,Miyata, Naoki
, p. 1055 - 1062 (2012/09/25)
Nitroxyl (HNO), a one-electron-reduced form of nitric oxide, has various biological activities, including a cardioprotective effect. Here, we first synthesized another, more hydrophilic photocontrollable HNO donor (3), which can release HNO in a spatially and temporally controlled manner, and then examined the properties of our series of compounds as practical HNO donors in a cellular system under photocontrol. We selected compound 2 as the preferred donor, and used it to show that calcitonin gene-related peptide (CGRP) can be upregulated in A549 cells via photocontrolled HNO release. This result demonstrates the suitability of this photocontrollable HNO donor for biological investigations.
Alternative photoinduced release of HNO or NO from an acyl nitroso compound, depending on environmental polarity
Matsuo, Kazuya,Nakagawa, Hidehiko,Adachi, Yusuke,Kameda, Eri,Tsumoto, Hiroki,Suzuki, Takayoshi,Miyata, Naoki
supporting information; experimental part, p. 3788 - 3790 (2010/08/07)
A hydrophilic hetero-Diels-Alder cycloadduct was synthesized as a novel photocontrollable donor of reactive nitrogen species. Production of either nitric oxide (NO) or nitroxyl (HNO) was photoinduced from this compound, depending on the environmental polarity.
One-pot curtius rearrangement processes from carboxylic acids
Leogane, Olivier,Lebel, Helene
scheme or table, p. 1935 - 1940 (2009/12/29)
An efficient and practical synthesis of amine derivatives from carboxylic acids is described using new one-pot Curtius rearrangement processes. The preparation of carbamate-protected amines and anilines, as well as ureas was achieved in good to excellent yields on a multigram scale. Georg Thieme Verlag Stuttgart.
Analogues of N-hydroxy-N′-phenylthiourea and N-hydroxy-N′-phenylurea as inhibitors of tyrosinase and melanin formation
Criton, Marc,Le Mellay-Hamon, Veronique
body text, p. 3607 - 3610 (2009/04/06)
A series of N-hydroxy-N′-phenylthiourea and N-hydroxy-N′-phenylurea analogues were prepared and evaluated as inhibitors of tyrosinase and melanin formation. The most active analogue 1 inhibited mushroom tyrosinase with an IC50 of around 0.29 μM
Photoactivatable HNO-releasing compounds using the retro-Diels-Alder reaction
Adachi, Yusuke,Nakagawa, Hidehiko,Matsuo, Kazuya,Suzuki, Takayoshi,Miyata, Naoki
supporting information; experimental part, p. 5149 - 5151 (2009/03/11)
We synthesized hetero-Diels-Alder cycloadducts from acyl nitroso derivatives and 9,10-dimethylanthracene, to be photo-inducible HNO-releasing agents and found that introduction of conjugated nitroaromatic groups effectively enhanced the responsiveness of HNO release to UV-A irradiation; we confirmed photoinduced HNO formation by EPR and GCMS analysis. The Royal Society of Chemistry.
Curtius rearrangement of aromatic carboxylic acids to access protected anilines and aromatic ureas
Lebel, Helene,Leogane, Olivier
, p. 5717 - 5720 (2007/10/03)
(Diagram presented) The reaction of a chloroformate or di-tert-butyl dicarbonate and sodium azide with an aromatic carboxylic acid produces the corresponding acyl azide, presumably through the formation of an azidoformate. The acyl azide undergoes a Curtius rearrangement to form an isocyanate derivative which is trapped either by an alkoxide or by an amine to form the aromatic carbamate or urea. The reaction conditions are compatible with a variety of functional groups and allow the synthesis of a number of aniline derivatives containing alkyl, halide, nitro, ketone, ether, and thioether substituents.
N-substituted hydroxyureas as urease inhibitors
Uesato, Shinichi,Hashimoto, Yuichiro,Nishino, Masaru,Nagaoka, Yasuo,Kuwajima, Hiroshi
, p. 1280 - 1282 (2007/10/03)
In order to seek a urease inhibitor more potent than hydroxyurea (1), its alkyl- or phenyl-substituted derivatives were synthesized and evaluated for their effect on the jack bean urease. Of 16 compounds tested, m-methyl-(10) and m-methoxy-phenyl substituted hydroxyurea (13) showed the most potent inhibitory activities against the enzyme.
