111-36-4Relevant academic research and scientific papers
Comparing hydrazine-derived reactive groups as inhibitors of quinone-dependent amine oxidases
Burke, Ashley A.,Severson, Elizabeth S.,Mool, Shreya,Solares Bucaro, Maria J.,Greenaway, Frederick T.,Jakobsche, Charles E.
, p. 496 - 503 (2017)
Lysyl oxidase has emerged as an important enzyme in cancer metastasis. Its activity has been reported to become upregulated in several types of cancer, and blocking its activity has been shown to limit the metastatic potential of various cancers. The small-molecules phenylhydrazine and β-aminopropionitrile are known to inhibit lysyl oxidase; however, issues of stability, toxicity, and poorly defined mechanisms limit their potential use in medical applications. The experiments presented herein evaluate three other families of hydrazine-derived compounds–hydrazides, alkyl hydrazines, and semicarbazides–as irreversible inhibitors of lysyl oxidase including determining the kinetic parameters and comparing the inhibition selectivities for lysyl oxidase against the topaquinone-containing diamine oxidase from lentil seedlings. The results suggest that the hydrazide group may be a useful core functionality that can be developed into potent and selective inhibitors of lysyl oxidase and eventually find application in cancer metastasis research.
A Mitsunobu-based procedure for the preparation of alkyl and hindered aryl isocyanates from primary amines and carbon dioxide under mild conditions
Horvath,Saylik,Elmes,Jackson,Lovel,Moody
, p. 363 - 366 (1999)
A Mitsunobu-based procedure for the preparation of alkyl and hindered aryl isocyanates in excellent yields from primary amines and carbon dioxide under very mild conditions is described.
Trifluoroacetic anhydride-catalyzed oxidation of isonitriles by DMSO: A rapid, convenient synthesis of isocyanates
Le, Hoang V.,Ganem, Bruce
, p. 2584 - 2585 (2011)
A smooth and efficient oxidation of isonitriles to isocyanates by sulfoxides is catalyzed by trifluoroacetic anhydride. With use of DMSO as the oxidant and 5 mol·% TFAA (dichloromethane, -60 to 0 °C), the process is complete in a few minutes, forming dimethyl sulfide as the only byproduct. The newly formed isocyanates may be used directly or isolated in high purity by solvent evaporation.
METHOD FOR PRODUCING CARBON DIOXIDE DERIVATIVE
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Paragraph 0033-0034; 0037, (2021/06/25)
PROBLEM TO BE SOLVED: To provide a method for producing a useful carbon dioxide derivative from carbon dioxide with low energy. SOLUTION: An amine is caused to absorb carbon dioxide, and without separating the carbon dioxide, it is then reacted with an acid catalyst and an olefin, thereby producing a carbon dioxide derivative, which serves as a raw material for polyurethane. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions
Hong, Wan Pyo,Tran, Van Hieu,Kim, Hee-Kwon
, p. 15890 - 15895 (2021/05/19)
A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.
Synthetic method for n-butyl isocyanate
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Paragraph 0030-0033, (2019/10/01)
The invention discloses a synthetic method for n-butyl isocyanate. The method comprises the following steps: selecting n-butylcarbamyl chloride, performing a reaction in an organic solvent for 8-15 hunder catalysis of a catalyst at a temperature of 80-160 DEG C, and performing thermal decomposition to obtain the n-butyl isocyanate, wherein the reaction equation is shown in the description. According to the synthetic method for the n-butyl isocyanate provided by the invention, the n-butylcarbamyl chloride is directly subjected to the reaction in the inert solvent to obtain the n-butyl isocyanate, and the chemical synthesis method eliminates safety hazards from a process source, and is a preparation method having a reasonable process, safe production, a high reaction yield, low production costs and substantially no three waste (waste water, waste gas and industrial residue) for the n-butyl isocyanate; and the method has an advanced technological route, avoids highly toxic phosgene and diphosgene, and has simple and safe operation, a high reaction yield, low production costs, less three waste (waste water, waste gas and industrial residue), larger implementation values and social andeconomic benefits.
Ebsulfur as a potent scaffold for inhibition and labelling of New Delhi metallo-β-lactamase-1 in vitro and in vivo
Su, Jianpeng,Liu, Jiayun,Chen, Cheng,Zhang, Yuejuan,Yang, Kewu
supporting information, p. 192 - 201 (2018/12/02)
The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has grown into an emerging threat, labelling and inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. Here, we report a potent covalent scaffold, ebsulfur, for targeting the protein in vitro and in vivo. Enzymatic kinetic study indicated that eighteen ebsulfurs gained except 1a–b and 1f inhibited NDM-1, exhibiting an IC50 value ranging of 0.16–9 μM, and 1g was found to be the best, dose- and time-dependent inhibitor with an IC50 of 0.16 μM. Also, these ebsulfurs effectively restored the antibacterial activity of cefazolin against E. coli expressing NDM-1, and the best effect was observed to be from 1g, 1i and 1n, resulting in an 256-fold reduction in MIC of the antibiotic at a dose of 16 μg/mL. The equilibrium dialysis study implied that the ebsulfur disrupted the coordination of one Zn(II) ion at active site of NDM-1. Labelling of NDM-1 using a constructed fluorescent ebsulfur Ebs-R suggested that the inhibitor covalently bound to the target through SDS-PAGE analysis in vitro. Also, labelling NDM-1 in living E. coli cells with Ebs-R by confocal microscopic imaging showed the real-time distribution change process of intracellular recombinant protein NDM-1. Moreover, the cytotoxicity of these ebsulfurs against L929 mouse fibroblastic cells was tested, and their capability to restore antibacterial activity of antibiotic against clinical strains E. coli EC08 producing NDM-1 was determined. The ebsulfur scaffold proposed here is valuable for development of the covalent irreversible inhibitors of NDM-1, and also for labelling the target in vitro and in vivo.
Amide compound, pharmaceutical composition, preparation method and application thereof
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Paragraph 0099-0102, (2018/09/11)
The invention provides an amide compound, a pharmaceutical composition, a preparation method and application thereof and belongs to the field of medicine. Structure of the amide compound is shown as aformula I. The preparation method includes: in an alkaline condition and in an organic solvent, allowing a compound I and a compound II to be in condensation reaction. The amide compound or pharmaceutically acceptable salt thereof have long-acting sensory and/or motion blocking activity, can be used for preparing long-acting local anesthetic or analgesic and is long in efficacy lasting time, little side effect and high in medication safety.
Method for synthesizing n-butyl isocyanate
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Paragraph 0021, (2016/10/07)
The invention discloses a method for synthesizing n-butyl isocyanate. The method comprises the following steps: weighing n-valeric acid and thionyl chloride according to the mole ratio of 1: 1, putting n-valeric acid and thionyl chloride in a round-bottomed flask, enabling an opening of the round-bottomed flask to be connected to a reflux condensing tube, of which an upper opening is provided with a calcium chloride drying tube, carrying out magnetic stirring, heating the round-bottomed flask to the temperature of 60-70 DEG C in oil bath, and carrying out reaction for 4-5 hours, so as to obtain a n-valeryl chloride crude product; and dissolving the crude product and a catalyst in an anhydrous toluene solvent, heating the solution to the temperature of 60-80 DEG C in a three-necked flask, enabling the three-necked flask to be connected to a thermometer, a reflux condensing tube, of which an upper opening is provided with a calcium chloride drying tube, and a flask cork respectively, carrying out magnetic stirring for 5-8 minutes, then, slowly adding drying sodium azide, of which the mole is equal to that of n-valeric acid, carrying out reaction until no gas is produced, keeping the reaction for 10-15 minutes, then, filtering out insolubles, and carrying out rotary evaporation to remove toluene, thereby obtaining n-butyl isocyanate. The method has the advantages of high yield, mild reaction conditions, simplicity in operation, short reaction time and little environmental pollution.
Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins
Chen, Yu,Su, Li,Yang, Xinying,Pan, Wenyan,Fang, Hao
, p. 9234 - 9239 (2015/11/27)
A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature.
