142-26-7Relevant academic research and scientific papers
Safe synthesis of alkylhydroxy and alkylamino nitramines
Antonsen, Simen,Aursnes, Marius,Gallantree-Smith, Harrison,Dye, Christian,Stenstr?m, Yngve
, (2016)
Three different protocols for the syntheses of hydroxyalkylnitramines are presented and compared. Safety issues regarding the synthesis of nitramines are also discussed.
Synthesis and properties of hypericins substituted with acidic and basic residues: Hypericin tetrasulfonic acid - A water soluble hypericin derivative
Falk, Heinz,Sarhan, Abd-El-Wareth A. O.,Tran, Huyen T. N.,Altmann, Robert
, p. 309 - 318 (1998)
Sulfonation of hypericin leads to its di-, tri-, and tetrasulfonic acid derivatives. The latter is soluble in water up to millimolar solutions. Homoaggregate formation (J-aggregates) was observed only above 5 · 10-4 mol/1. In water solutions, the tetrasulfonic acid hypericin derivative was found to be present as its bay-phenolate with most of the sulphonic acids dissociated. Thus, the first water soluble hypericin derivative, which in contrast to hypericin is not prone to homoassociation, is presented. Hypericin tetrtasulfonic acid forms heteroassociates with serum albumin, DNA, and γ-cyclodextrin. Hypericin derivatives with primary and tertiary amino group appendages at the hypericin methyl groups were synthesized. However, upon salt formation or quaternization these derivatives became virtually insoluble in all common solvents including water.
Switching Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine
Sayama, Misa,Uwamizu, Akiharu,Ikubo, Masaya,Chen, Luying,Yan, Ge,Otani, Yuko,Inoue, Asuka,Aoki, Junken,Ohwada, Tomohiko
, p. 10059 - 10101 (2021/07/28)
Three human G protein-coupled receptors (GPCRs)—GPR34/LPS1, P2Y10/LPS2, and GPR174/LPS3—are activated specifically by lysophosphatidylserine (LysoPS), an endogenous hydrolysis product of a cell membrane component, phosphatidylserine (PS). LysoPS consists of-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages. We previously generated potent and selective GPCR agonists by modification of the three modules and the ester linkage. Here, we show that a novel modification of the hydrophilic serine moiety, that is, N-acylations of the serine amine, converted a GPR174 agonist to potent GPR174 antagonists. Structural exploration of the amide functionality provided access to a range of activities from agonist to partial agonist to antagonist. The present study would provide a new strategy for the development of lysophospholipid receptor antagonists.
Preparation method of N-vinyl alkylamide
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Paragraph 0067-0068; 0073-0074, (2020/12/29)
The invention relates to the technical field of vinyl compound production, in particular to a preparation method of Nvinyl alkyl amide. The preparation method comprises the following steps: A) under the action of a composite basic catalyst, reacting acetaldehyde with alkylamide to obtain Nhydroxyethyl alkylamide, and carrying out esterification reaction on the obtained Nhydroxyethyl alkylamide andacid anhydride to obtain an ester compound; wherein the composite basic catalyst comprises an inorganic base and an amine compound; and B) carrying out medium-temperature cracking on the ester compound, and carrying out vacuum distillation to obtain the Nvinyl alkylamide. Research finds that inorganic base and amine compounds are adopted as catalysts at the same time, so that the dosage of a basic catalyst required by reaction of Nhydroxyethyl alkylamide and anhydride can be remarkably reduced, the temperature required by subsequent cracking reaction is reduced, a reaction system tends to bemilder, and the reaction yield is improved. The yield and the purity of a reaction product can be remarkably improved while the energy consumption is reduced.
Formation of carbon–nitrogen bonds in carbon monoxide electrolysis
Jouny, Matthew,Lv, Jing-Jing,Cheng, Tao,Ko, Byung Hee,Zhu, Jun-Jie,Goddard, William A.,Jiao, Feng
, p. 846 - 851 (2019/09/03)
The electroreduction of CO2 is a promising technology for carbon utilization. Although electrolysis of CO2 or CO2-derived CO can generate important industrial multicarbon feedstocks such as ethylene, ethanol, n-propanol and acetate, most efforts have been devoted to promoting C–C bond formation. Here, we demonstrate that C–N bonds can be formed through co-electrolysis of CO and NH3 with acetamide selectivity of nearly 40% at industrially relevant reaction rates. Full-solvent quantum mechanical calculations show that acetamide forms through nucleophilic addition of NH3 to a surface-bound ketene intermediate, a step that is in competition with OH– addition, which leads to acetate. The C–N formation mechanism was successfully extended to a series of amide products through amine nucleophilic attack on the ketene intermediate. This strategy enables us to form carbon–heteroatom bonds through the electroreduction of CO, expanding the scope of products available from CO2 reduction.
Method for preparing 3-ketomorpholine
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Paragraph 0062-0064, (2019/03/26)
The invention relates to a method for preparing 3-ketomorpholine. The method comprises the following steps: protecting the amino group of ethanolamine firstly, then carrying out a reaction of amino group protected ethanolamine with alkyl haloacetate, performing deprotection on the prepared product, and performing ring closure so as to obtain 3-ketomorpholine. The method has the advantages of simple practical operation, low equipment requirements, high yield and low three waste, and is suitable for industrial large-scale production.
Metal-Free O-Selective Direct Acylation of Amino Alcohols Through Pseudo-Intramolecular Process
Yokoyama, Soichi,Shibauchi, Hiroshi,Asahara, Haruyasu,Nishiwaki, Nagatoshi
, p. 1125 - 1133 (2019/02/01)
Efficient α-aryl-β-keto ester acylation of amine accompanied by the elimination of ethyl phenylacetate was achieved owing to the pseudo-intramolecular process. The eliminated ethyl phenylacetate could be recycled by conversion into an α-aryl-β-keto ester upon treatment with an acyl chloride in the presence of lithium bis(trimethylsilyl)amide, by which the atom economy considerably increased. Acylation using an α-aryl-β-keto ester is highly sensitive to the bulkiness of the nucleophile, which facilitated the regioselective-acylation of the less hindered amino group in diamine without protecting the other. The transacylation of α-aryl-β-keto ester with N-alkylamino alcohol resulted in chemoselective O-acylation without protecting the amino group because the hydroxy group was attracted to the reaction site of the keto ester by forming an ammonium salt. Transacylation was demonstrated to be a practically useful tool for organic synthesis because this protocol can be conducted under mild conditions with simple manipulations in the absence of any additives such as metal catalyst and base.
Pivotal role of intramolecular catalysis in the selective acetylation of alkyl amines
Nishida, Elvis N.,Vitto, Ramon,Peixoto, R?mulo C.R.,Nome, Faruk,Souza, Bruno S.
, (2018/04/14)
Preparation of amides by the use of esters as the "acyl donor" is less explored because they are less reactive and usually more steric demanding than conventional acid halides and anhydrides. Here, we report that 3-acetoxy-2-naphthoic acid, an aspirin analogue, can be used as a mild amine acetylating agent in ethanol at 25°C. The reaction is sensitive to steric and polar effects of the attacking amine, and the rate constants can be appropriately fitted by the Pavelich-Taft correlation. Density functional theory calculations used to study all reaction steps indicate that the o-carboxy group plays a pivotal role, guiding the attacking amine and accelerating the reaction. The reaction can be conveniently used for the acylation of a variety of primary and secondary amines.
FUMARATE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USE
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Paragraph 0454, (2017/02/24)
Fumarate compounds, pharmaceutical compositions comprising the fumarate compounds, and methods of using fumarate compounds and pharmaceutical compositions for treating neurodegenerative, inflammatory, and autoimmune disorders including multiple sclerosis, psoriasis, irritable bowel disorder, ulcerative colitis, arthritis, chronic obstructive pulmonary disease, asthma, Parkinson's disease, Huntington's disease, and amyotrophic lateral sclerosis are disclosed.
FUMARATE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USE
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Paragraph 0634, (2017/02/24)
Fumarate compounds, pharmaceutical compositions comprising the fumarate compounds, and methods of using fumarate compounds and pharmaceutical compositions for treating neurodegenerative, inflammatory, and autoimmune disorders including multiple sclerosis, psoriasis, irritable bowel disorder, ulcerative colitis, arthritis, chronic obstructive pulmonary disease, asthma, Parkinson's disease, Huntington's disease, and amyotrophic lateral sclerosis are disclosed.
