- Selective mono- or dialkoxylation of 2,4,6-trichloro-1,3,5-triazine in solid-liquid phase transfer conditions
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In solid-liquid phase transfer conditions, both the primary and the secondary alcohols react cleanly with 2,4, 6-trichloro-1,3,5-triazine to give the corresponding mono or dialkoxy derivatives depending on the reagent molar ratio.
- Menicagli,Malanga,Peluso
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- Design and synthesis of 1,3,5-triazine derivatives as novel inverse agonists of nuclear retinoic acid receptor-related orphan receptor-γ
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1,3,5-Triazine structure is a versatile chemical species for development of functional molecules, including biologically active compounds. We report herein the design, synthesis and biological evaluation of novel inverse agonists of nuclear retinoic acid receptor-related orphan receptor-γ (RORγ), in which the 2-anilino-1,3,5-triazine moiety was used as a scaffold for structural development. Among the synthesized compounds, 13b exhibited potent and selective inverse agonistic activity toward RORγ, being more potent than the lead compound T0901317 (7). The results suggest that the 2-anilino-1,3,5-triazine moiety is a useful scaffold for development of inhibitory ligands of nuclear receptors.
- Kaitoh, Kazuma,Toyama, Hirozumi,Hashimoto, Yuichi,Fujii, Shinya
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- TRIAZINE-2,4-DIONE DERIVATIVE AND MANUFACTURING METHOD THEREFOR
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PROBLEM TO BE SOLVED: To provide a novel triazine-2,4-dione derivative having 2 glycidyl groups as a substituent binding to a nitrogen atom, and further a substituent containing an alkoxy group, and a manufacturing method therefor. SOLUTION: There is provided a triazine-2,4-dione derivative, which is represented by the following formula (1), and is liquid as a state of the material at 25°C, 101.3 kPa. In the formula, R1 represents an alkyl group having 1 to 10 carbon atoms, R2 and R3 represent each independently an alkylene group having 1 to 5 carbon atoms, m and n represent each independently an integer of 0 to 5, and total number of carbon atoms of -(R3O)n(R2O)mR1 group is 1 to 18. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0021
(2019/07/23)
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- Design, Synthesis and Biological Evaluation of Novel Nonsteroidal Progesterone Receptor Antagonists Based on Phenylamino-1,3,5-triazine Scaffold
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We report here the development of phenylamino-1,3,5-triazine derivatives as novel nonsteroidal progesterone receptor (PR) antagonists. PR plays key roles in various physiological systems, including the female reproductive system, and PR antagonists are promising candidates for clinical treatment of multiple diseases. By using the phenylamino-1,3,5-triazine scaffold as a template structure, we designed and synthesized a series of 4-cyanophenylamino-1,3,5-triazine derivatives. The synthesized compounds exhibited PR antagonistic activity, and among them, compound 12n was the most potent (IC50=0.30μM); it also showed significant binding affinity to the PR ligand-binding domain. Docking simulation supported the design rationale of the compounds. Our results suggest that the phenylamino-1,3,5-triazine scaffold is a versatile template for development of nonsteroidal PR antagonists and that the developed compounds are promising lead compounds for further structural development of nonsteroidal PR antagonists.
- Kaitoh, Kazuma,Nakatsu, Aki,Mori, Shuichi,Kagechika, Hiroyuki,Hashimoto, Yuichi,Fujii, Shinya
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p. 566 - 575
(2019/07/22)
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- KINETICS OF FORMATION OF MONOALKOXY-s-TRIAZINES FROM CYANURIC CHLORIDE.
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2-R-alkoxy-4,6-dichloro-s-triazines (I) are used as intermediates for synthesis of herbicides, and are obtained by reactions of 2,4, 6-trichloro-s-triazine (II) (cyanuric chloride) with various alcohols in aqueous-organic mixtures in presence of hydrogen chloride acceptors. The purpose of this work was to study the quantitive relationships of the main reaction of cyanuric chloride alkoxylation and of the competing reactions of hydrolysis and alkoxylation of compound (I), for optimization of production of monoalkoxy-s-triazines. It is found that the reaction temperature has a significant influence on the yield of 2-(2-R-ethoxy)-4, 6-dichloro-s-triazine; decrease of temperature raises the yield of (I) owing to decrease of the contributions of hydrolysis of compounds (I) and (II) and alkoxylation of (I). The asolute values of the rate constants of hydrolysis (k//3, k//4) and alkoxylation (k//2) decrease more rapidly than k//1 with decrease of temperature. This makes it possible to raise the selectivity of the process by raising the alkali concentration and lowering the reaction temperature.
- Marchukov,Koryakov,Lopachenok,V'yunov,Ginak
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p. 574 - 578
(2007/10/02)
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- IMPROVEMENT OF THE SELECTIVITY OF ALKOXYLATION OF CYANURIC CHLORIDE.
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Study of the quantitative relationships of the alkoxylation reaction and optimization of the complex reaction based on a mathematical model show that individual monoalkoxy-s-triazines free from 5-15% of dialkoxy-s-triazines cannot be obtained in aqueous acetone solutions. It is found that if the reaction is conducted in the basic bipolar aprotic solvent dimethylacetamide it proceeds selectively with exclusive formation of monoalkoxy-s-triazines. It can be seen from the data that the nature of the solvent does not affect selectivity of the reaction significantly. It is shown that when cyanuric chloride reacts with amides left bracket dimethylformamide (DMFA), N-methylformamide right bracket hygroscopic hydrolytically unstable products of the salt type are formed. The intermediates react with nucleophiles, such as aniline, to form substituted triazines. The reaction proceeds analogously with alcohols, and the hydrogen chloride evolved is bound irreversibly by dimethylacetamide.
- Koryakov,Koshokov,Nikitin,Marchukov,V'yunov
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p. 1309 - 1310
(2007/10/02)
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- HALOGENATED ETHERS. XXI. EFFECT OF TEMPERATURE AND SUBSTITUENT ON THE KINETIC OF THE FORMATION OF 2-(2-R-ETHOXY)-4,6-DICHLORO-SYM-TRIAZINES
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The effect of temperature on the kinetics of the formation of 2-(2-R-ethoxy)-4,6-dichloro-sym-triazines from 2,4,6-trichloro-sym-triazine and 2-R-ethanol in the presence of alkali was investigated.The low values of the activation energy and the large negative values of the entropy indicate the participation of a stable intermediate in the investigated complex many-stage reaction.The mechanism of the process and the characteristics of the manifestation of isokinetic relationships are discussed.
- Marchukov, V. A.,Nikitin, O. A.,V'yunov, K. A.,Ginak, A. I.
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p. 2282 - 2286
(2007/10/02)
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