- Synthesis of novel 3-substituted-5H-benzo[5,6][1, 4]thiazino[3,2-e][1,2,4]triazines and their 15-lipoxygenase inhibitory activity
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A new group of 3-substituted-5H-benzo[5,6][1,4]thiazino[3,2-e][1,2,4]triazines was designed, synthesized and evaluated as inhibitors of 15-lipoxygenase (15-LO), and the results were compared with those of standard ligand 4-methyl-2-(4-methylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine (4-MMPB). Among the newly designed ligands, compound 9e showed the best IC50 of 15-LO inhibition (IC50?=?38?μM). The docking calculations were performed in MOE software based on the function of force-field scoring, in order to study the interaction of these new compounds and standard ligand with 15-LO. The docking study implied that these ligands have hydrogen bond interaction with the residue of active site of 15-LO.
- Mohammadi, Ali,Eshghi, Hossein,Bakavoli, Mehdi,Hadizadeh, Farzin,Moradi, Hassanali
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- An improved synthesis of the 5-HT1A receptor agonist Eptapirone free base
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Eptapirone free base, F11440,4-methyl-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1,2,4-triazine-3,5(2H,4H)-dione, represents a potent and selective 5-HT1A receptor agonist with high efficacy and the potential to regulate anxiety disorders. Herein, we report a method to retro-synthesize eptapirone free base. The compound consists of heterocyclic aromatic portion and aliphatic portion, and the synthetic route consisted of a total of nine steps with an overall yield of 8.8% starting from the commercially available materials. The key steps in the synthetic method involved: (1) using sodium hydroxide and ethylene glycol as solvent resulted in a better cyclization and yield (61.6%) of 1,2,4-triazine-3,5(2H,4H)-dione; (2) an acceptable yield (63.1%) of 4-tert-butyl(pyrimidin-2-yl)piperazine-1-carboxylate was obtained under an optimized conditions of using triethylamine as a base, ethanol as a solvent, and a reaction temperature of 50?°C for 16?h with non-metal catalysis and less byproducts; (3) the reaction step of eptapirone could get a better yield (49.6%) with an optimized condition of potassium carbonate as a base, acetonitrile as a solvent, NaI as a catalyst, and a reaction temperature of 50?°C for 12?h by nucleophilic substitution reaction. The main advantages of this route were an acceptable product purity, the commercial availability of all starting materials and the absence of high temperature, high pressure and noble metal catalysts, which could result in more feasible commercial applications.
- Peng, Wei,Chen, Jian,Liu, Hui,Li, Xiufang,Deng, Zhiwei,Yuan, Jing,Peng, Yizhou,Yang, Yanjing,Zhong, Shian
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p. 1321 - 1331
(2019/05/06)
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- Full synthesis method of eptapirone
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The invention discloses a full synthesis method of eptapirone. The full synthesis method comprises the following steps: (1) taking aminourea hydrochloride and trichloracetic aldehyde as raw materialsand carrying out a series of reaction to obtain 2-[2-(aminocarbonyl)hydrazono](CD-1); (2) synthesizing 6-azauracil(CD-2) by the 2-[2-(aminocarbonyl)hydrazono] under the action of sodium hydroxide; (3)taking the 6-azauracil and acetic anhydride to react to obtain 2-acetyl-2H-[1,2,4]triazine-3,5(2H,4H)-diketone(CD3); (4) taking the 2-acetyl-2H-[1,2,4]triazine-3,5(2H,4H)-diketone to react to obtain3-methyl-6-azauracil(CD-4); (5) taking the 3-methyl-6-azauracil to react to obtain 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-diketone(CD-5); (6) taking 2-bromopyrimidine, 1-Boc-piperazine and triethylamine to react to obtain 4-(pyrimidine-2-yl)piperazine-1-tert-butyl formate(CD-6); furthermore, reacting to obtain 2-(1-piperazinyl)pyrimidine hydrochloride (1 to 1)(CD-7); (7) taking the 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-diketone in step (5) to react with the 2-(1-piperazinyl)pyrimidine hydrochloride in step (6) to obtain the eptapirone(CD-8). The product disclosed by the invention is high in purity and yield and is suitable for industrialized production.
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Paragraph 0089; 0102; 0103; 0104
(2018/09/12)
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- PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
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The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.
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- Comparative studies for selective deprotection of the N-arylideneamino moiety from heterocyclic amides: kinetic and theoretical studies. Part 2
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4-Benzylideneamino-1,2,4-triazine-3,5(2H,4H)-diones (2-5), 6-styryl-1,2,4-triazine-3,5(2H,4H)-dione (6), and 6-styryl-2,3-dihydro-3-thioxo-1,2,4-triazin-5(4H)-one (7) were synthesized and pyrolyzed in the gas phase. The kinetic effect of changing the substituent on the triazine ring from hydrogen to methyl, phenyl, and styryl was measured. Analyses of the pyrolyzates of 2-5 showed the elimination products to be benzonitrile and the triazine fragment, while the pyrolyzates of 6 and 7 reveal the formation of cis- and trans-cinnamonitriles. Theoretical study of the pyrolysis reactions of 2-5 using an ab initio SCF method was investigated.
- Al-Awadi, Nouria A.,Ibrahim, Yehia A.,Dib, Hicham H.,Ibrahim, Maher R.,George, Boby J.,Abdallah, Mariam R.
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p. 6214 - 6221
(2007/10/03)
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- Substitutes 2-aryl-1,2,4-triazine-3,5-di(thi)one
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The invention relates to novel substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones of the general formula (I), in which Q1, Q2, R1, R2, R3, R4, R5 and R6 are each as defined in the description, and to processes for their preparation and to their use as herbicides.
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