- Preparation method 3 -amino -5 -alkyl isoxazole
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The invention discloses a preparation method of 3-amino-5-alkyl isoxazole, realizes preparation through two steps and belongs to the technical field of organic chemistry. By starting from easily obtained aldehyde, after the addition with acetonitrile under the existence of metal alkali, an intermediate of hydroxy nitrile is obtained; then, the hydroxy nitrile reacts with hydroxylamine; ring closing reaction is performed under the existence of Lewis acid; after autoxidation, the 3-amino-5-alkyl isoxazole is obtained. The raw materials in the reaction process are very commons; chloroform or tetrachloromethane in a traditional method is avoided; potential industrial amplification prospects are realized.
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Paragraph 0034-0035; 0038; 0039-0040; 0043
(2020/06/05)
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- Drug Discovery against Psoriasis: Identification of a New Potent FMS-like Tyrosine Kinase 3 (FLT3) Inhibitor, 1-(4-((1H-Pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-3-fluorophenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea, That Showed Potent Activity in a Psoriatic Animal Model
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Psoriasis is a chronic T-cell-mediated autoimmune disease, and FMS-like tyrosine kinase 3 (FLT3) has been considered as a potential molecular target for the treatment of psoriasis. In this investigation, structural optimization was performed on a lead compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea (1), which showed a moderate inhibitory activity againt FLT3. A series of pyrazolo[3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship analysis led to the discovery of a number of potent FLT3 inhibitors. One of the most active compounds, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(5-tert-butylisoxazol-3-yl)urea (18b), was then chosen for in-depth antipsoriasis studies because this compound displayed the highest potency in a preliminary antipsoriasis test. Compound 18b exhibited significant antipsoriatic effects in the K14-VEGF transgenic mouse model of psoriasis, and no recurrence was found 15 days later after the last administration. Detailed mechanisms of action of compound 18b were also investigated. Collectively, compound 18b could be a potential drug candidate for psoriasis treatment.
- Li, Guo-Bo,Ma, Shuang,Yang, Ling-Ling,Ji, Sen,Fang, Zhen,Zhang, Guo,Wang, Li-Jiao,Zhong, Jie-Min,Xiong, Yu,Wang, Jiang-Hong,Huang, Shen-Zhen,Li, Lin-Li,Xiang, Rong,Niu, Dawen,Chen, Ying-Chun,Yang, Sheng-Yong
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p. 8293 - 8305
(2016/10/03)
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- THIENO[3,2-D]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES
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Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases.
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Paragraph 0288; 0289; 0290
(2015/01/06)
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- Synthesis and Biological Evaluation of Chromenylurea and Chromanylurea Derivatives as Anti-TNF-a agents that Target the p38 MAPK Pathway
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A series of 1-aryl-3-(2H-chromen-5-yl)urea and 1-aryl-3-(chroman-5-yl)urea derivatives were designed, synthesized and evaluated for their inhibitory activities towards TNF-a production in lipopolysaccharide-stimulated THP-1 cells. The most active compound, 40g, inhibited TNF-a release with an IC50 value of 0.033 μM, which is equipotent to that of BIRB796 (IC50 = 0.032 μM).
- Li, Xingzhou,Zhou, Xinming,Zhang, Jing,Wang, Lili,Long, Long,Zheng, Zhibing,Li, Song,Zhong, Wu
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p. 2004 - 2028
(2014/03/21)
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- THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES
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Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases
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Page/Page column 42; 43
(2013/07/19)
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- The synthesis and properties of highly organosoluble metal(II) complexes with hydrazone ligands derived from pivaloylacetonitrile
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Using pivaloylacetonitrile as starting material and coupling component, a novel hydrazone ligand and four, highly organosoluble metal(II) complexes were synthesized via the procedure of oximation, cyclization, diazotization, coupling and metal chelation. In addition to elemental analysis, the structures of the novel compounds were postulated based on a series of spectroscopic methods. Smooth thin films of these metal(II) complexes on K9 glass substrates were prepared by spin-coating from 2,2,3,3-tetrafluoro-1-propanol solutions. The behaviour and relationships of the absorption bands both in solution and in spin-coated films are discussed; the thermal properties, photostability and the solubility of the metal(II) complexes were investigated. The synthesized Ni(II) complex exhibited a remarkable combination of excellent solubility and photostability, suitable absorption band and desirable thermal properties and, therefore, offers the potential of becoming a recording material for the recordable blu-ray disc system.
- Chen, Zhimin,Wu, Yiqun,Gu, Donghong,Gan, Fuxi
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experimental part
p. 42 - 49
(2010/11/04)
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- PRACTICAL SYNTHESIS OF 3-AMINO-5-tert-BUTYLISOXAZOLE FROM 4,4-DIMETHYL-3-OXOPENTANENITRILE WITH HYDROXYLAMINE
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A good yield of 3-amino-5-tert-butylisoxazole (3) was obtained regioselectively from a reaction of 4,4-dimethyl-3-oxopentanenitrile (1) with hydroxylamine in the aqueous solution of which was adjusted to weak basic, followed by treatment of the resulting
- Takase, Akira,Murabayashi, Akira,Sumimoto, Shinzaburo,Ueda, Shiro,Makisumi, Yasuo
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p. 1153 - 1158
(2007/10/02)
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- Isoxazolotriazindiones and plant growth inhibiting use thereof
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Certain isoxazolotriazinediones, useful for controlling the growth of unwanted plants.
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- Analytical Studies on Isoxazoles. VI. Colorimetric Determination of Some Isoxazole Herbicides with p-Dimethylaminocinnamaldehyde
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Some isoxazole herbicides were determined by a colorimetric method with p-dimethylaminocinnamaldehyde (DACA) as the reagent.The compounds (2, 3 and 4) having various substituents at the 3-position were hydrolyzed to 3-amino-5-tert-butylisoxazole (5).The assay method was based on the coloration of 5 with DACA, which was reported previously.The optimum hydrolysis conditions were determined.Compound 5 was obtained from 2, 3 and 4 with sufficient recoveries under neutral, alkaline and acidic conditions, respectively.The raw materials could thus be evaluated effectively by simple assay methods.Keywords - isoxazole herbicide; 5-tert-butylisoxazole-3-substituted; colorimetric assay method; p-dimethylaminocinnamaldehyde; Schiff base; 3-amino-5-tert-butylisoxazole; hydrolysis condition.
- Kitagawa, Takayasu,Ohsugi, Masako,Hirai, Eizo
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p. 2841 - 2844
(2007/10/02)
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- Analytical Studies on Isoxazoles. V. Colorimetric Determination of Isouron and Its Isomer with p-Dimethylaminocinnamaldehyde
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Isouron (1) and its isomer, 1-(3-tert-butylisoxazol-5-yl)-3,3-dimethylurea (2), were determined by a colorimetric method with p-dimethylaminocinnamaldehyde (DACA) as the reagent.Compounds 1 and 2 were hydrolyzed to give 3-amino-5-tert-butylisoxazole (3) a
- Kitagawa, Takayasu,Iwakura, Kumiko,Ohsugi, Masako,Hirai, Eizo
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p. 2736 - 2744
(2007/10/02)
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- Method for preparing 3-amino-5-(t-butyl)isoxazole
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3-Amino-5-(t-butyl)isoxazole, in optimum yield, is prepared in a stepwise manner by reacting a lower alkyl pivalate and acetonitrile in the presence of a base to yield pivalyl acetonitrile, which in turn is allowed to react with hydroxylamine under controlled conditions of pH to yield the desired compound. The compound is a useful intermediate for the preparation of isoxazole derivatives having utility as herbicides.
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- Process for the production of 3-amino-5-t-butylisoxazole
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3-Amino-5-t-butylisoxazole is prepared by reacting pivaloylacetonitrile with hydroxylamine in aqueous medium under basic conditions and treating the reaction products with an acid. The process is economical and industrial.
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- Process for the production of 3-aminoisoxazoles
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3-Aminoisoxazoles of the formula: STR1 (wherein R is C1 -C6 alkyl, phenyl or halo-phenyl) are prepared by reacting a β-ketonitrile of the formula: (wherein R is as defined above) with a compound of the formula: (wherein Y is C1 -C6 alkoxy or C1 -C6 alkylthio) in the presence of an acid in a solvent to give an iminium salt of the formula: STR2 (wherein X is the residue of said acid; R and Y are each as defined above) and further reacting the iminium salt with hydroxylamine in an inert solvent.
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