- Synthesis, characterization, and antimicrobial screening of s-triazines linked with piperazine or aniline scaffolds
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Two series of s-triazines linked with piperazine or aniline scaffolds (4a-i and 5a-j) were synthesized and evaluated for their in vitro biological efficacy against Gram positive and Gram negative bacteria (Klebsiella pneumoniae MTCC 109, Pseudomonas aerug
- Lakum, Harshad P.,Desai, Dhara V.,Chikhalia, Kishor H.
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- Preparation method of 2,4-dichloro-6-(4-methoxyphenyl)-1,3,5-triazine
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The invention discloses a preparation method of 2,4-dichloro-6-(4-methoxyphenyl)-1,3,5-triazine. According to the preparation method, p-methoxyphenylboronic acid and cyanuric chloride are taken as raw materials and a magnetic silicon dioxide supported palladium complex is taken as a catalyst, an alkali and a solvent are added, Suzuki coupling reaction is conducted, a catalyst phase is separated out after the reaction, the solvent is recovered from a product phase, and finally, recrystallizing and drying are conducted to obtain a pure product 2,4-dichloro-6-(4-methoxyphenyl)-1,3,5-triazine. The catalyst can be separated, recovered and recycled through an external magnetic field, the magnetic catalyst is high in activity, high in catalytic efficiency and high in reaction selectivity, the product purity is high, operation is simple, reaction conditions are mild, the reaciton process is clean and friendly, and the method provided by the invention is a novel green and efficient preparation method.
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Paragraph 0030-0057
(2021/04/07)
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- Manufacturing method of triazine-based compound and derivative thereof
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The present invention relates to a triazine-based compound and a process for producing the same. The triazine compound according to an embodiment of the present invention may be prepared by reacting cyanuric acid (Cyanuric Chloride), anisole (anisole) and resorcinol (Resorcinol) to produce a triazine-based compound represented by Formula 1. Chemical Formula 1.
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Paragraph 0124-0148
(2021/05/25)
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- TRIAZINE UV ABSORBERS AND A PROCESS FOR THE PREPARATION THEREOF
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The presently claimed invention relates to novel, highly efficient triazine UV absorbers and a general process for the preparation UV absorber compounds from natural precursors.
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Page/Page column 58
(2021/07/02)
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- Polymerizable UV absorbers for the UV stabilization of polyesters. I. Design, synthesis and polymerization of a library of UV absorbing monomers
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UV stabilizers, such as Tinuvin 1577, are organic additives that are used in the polymer industry to suppress polymer photodegradation, however leaching of the stabilizers from polymers is a significant practical issue which limits the effectiveness of the stabilizers and restricts polymer lifetimes. Novel, polymerizable UV stabilizers were synthesised and copolymerized with bis(2-hydroxyethyl) isophthalate to yield poly(ethylene isophthalate) copolymers where the UV stabilizers are bound covalently into the polymer chains. This strategy prevents leaching of stabilizers from polymers over time, and is expected to lead to enhanced UV protection of polymers compared to the admixing of polymers with UV stabilizers of low molar mass.
- Cormack, Peter A.G.,Erdemli, Omer C.,Sankey, Stephen W.
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- A new class of 1,3,5-triazine-based selective estrogen receptor degraders (SERDs): Lead optimization, molecular docking and dynamic simulation
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Selective estrogen receptor degrader (SERD) that acts as not only ER antagonist, but also ER degrader, would be useful for the treatment for drug-resistance ER+ breast cancer. However, most of currently available SERD candidates involve very limited molecular scaffolds and are still in clinical trials. In this study, we introduced a 1,3,5-triazine ring into a homobibenzyl motif extracted from amounts of ER ligands and synthesized sixteen SERDs bearing acrylic acid or acrylic amide side chains that possess both ERα antagonism and degradation properties. And all compounds were screened for their anti-proliferative activity against ER+ MCF-7 and Ishikawa cell lines. Among them, compound XHA1614 displayed potent growth inhibition activity against MCF-7 and Ishikawa cells with IC50 values of 3.15 μM and 3.11 μM, respectively. Moreover, XHA1614 could dramatically degrade ER level at 1 nM in a Western blotting assay and afforded an outstanding antagonistic activity via suppressing the expression of progesterone receptor messenger RNA in MCF-7 cells in a RT-PCR assay. Further molecular docking and dynamic simulation on properly selected derivative furnished insights into its binding profile within ERα. Our findings suggest that the 1,3,5-triazine core was a feasible alternative to currently reported SERD scaffold, and provide information that will be useful for further development of promising SERDs candidates for breast cancer therapies.
- Huang, Ali,Lu, Xiang,Luo, Guoshun,Mao, Jiashun,Sun, Liang,Xiang, Hua,Xiao, Maoxu
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- Method for synthesizing triazine compound by Friedel-Crafts reaction micro-channel method
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The invention discloses a method for synthesizing a triazine compound by a Friedel-Crafts reaction micro-channel method. The method comprises the following steps: carrying out mixing dissolving on cyanuric chloride represented by a formula (I), a compound represented by a formula (II), a Lewis acid as a catalyst and an organic solvent to obtain a reaction solution for later use; replacing and exhausting the air in a micro-channel reactor by using nitrogen, injecting the prepared reaction liquid into the micro-channel reactor through a metering pump, carrying out a Friedel-Crafts reaction, controlling the reaction temperature to be 0-120 DEG C, controlling the reaction retention time to be 10-180 minutes, and carrying out post-treatment on the reaction liquid flowing out of the micro-channel reactor to obtain the triazine compound represented by a formula (III), wherein in the formula (II) and the formula (III), the substituent R1 is hydrogen, methyl, hydroxyl, methoxy or chlorine atom,and the substituent R2 is hydrogen, methyl or hydroxyl. By adopting the micro-channel reactor, the corresponding reaction conditions are optimized, the mass transfer and heat transfer effects of thereaction are good, the reaction time is shortened, side reactions are reduced, and the yield of the target product is high.
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Paragraph 0014-0016; 0023-0032
(2020/05/02)
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- IMPACT OF TRACE ELEMENTS IN THE GRIGNARD REACTION
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The present invention relates to an improved process for preparing 2,4-dichloro-6-(4- methoxyphenyl)-1,3,5-triazine (DICAT) comprising reacting 4-bromoanisole with magnesium, and reacting the resulting Grignard reagent with cyanuric chloride, wherein the magnesium comprises additional metals as impurities in an amount of less than 0.027 % by weight, based on the total weight of the magnesium.
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Page/Page column 8
(2020/10/18)
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- 1,3,5-triazine compound or medicinal salt thereof as well as preparation method and application thereof
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The invention discloses a 1,3,5-triazine compound of a formula (I) or a formula (II) shown in the specification, or a medicinal salt thereof, and furthermore discloses a preparation method and application of the compound or the medicinal salt thereof. The compound or the medicinal salt thereof disclosed by the invention can be adopted to prepare medicines for treating human breast cancer and endometrial cancer.
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Paragraph 0147-0148
(2019/10/04)
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- Preparation method of 2,4-dichloro-6-(4-methoxyphenyl)-1,3,5-triazine
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The invention discloses a preparation method of 2,4-dichloro-6-(4-methoxyphenyl)-1,3,5-triazine. The method uses 1,3,5-triazine and p-methoxyphenylboronic acid as starting materials, a nickel-phosphine complex is taken as a catalyst, and the 2,4-dichloro-6-(4-methoxybenzene)-1,3,5-triazine is prepared in one step. The preparation method is simple in process, convenient to operate and mild in reaction condition, the shortcoming of the poor selectivity of a Friedel-Crafts alkylation method is overcome, the pressure brought by an anhydrous aluminum trichloride catalyst on the treatment of the three wastes is avoided, and the requirements of green environmental protection are met.
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Paragraph 0012-0015
(2019/11/12)
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- An ultraviolet absorbent the day executes S intermediate preparation method
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The invention relates to an ultraviolet absorbent the day executes S intermediate preparation method, in particular to a 2, 4 - double-(2, 4 - dihydroxy-phenyl) - 6 - (methoxyphenyl) - 1, 3, 5 - triazine. The invention in step (1) in the specific catalyst, direct catalytic cyanuric chloride and anisole for carrying out the alkylation reaction, to obtain intermediate 2, 4 - dichloro - 6 - (methoxyphenyl) - 1, 3, 5 - triazine solution, then put in the resorcinol, sulfolane, catalyst, the reaction is carried out, the filter, the filtrate is hydrolyzed, separating solid, filtered and the solid water washing, drying, to obtain 2, 4 - double-(2, 4 - dihydroxy-phenyl) - 6 - (methoxyphenyl) - 1, 3, 5 - triazine. The invention atom economy high, low material cost, the production low safety risk and less environmental pollution.
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Paragraph 0016-0033
(2019/07/01)
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- Manufacturing method of triazine-based compound and derivative thereof
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The present invention relates to a triazine-based compound, and a method for manufacturing derivatives thereof. The method for manufacturing the triazine-based compound according to an embodiment of the present invention can manufacture the triazine-based compound represented by chemical formula 1 by conducting a reaction of cyanuric chloride, anisole, and resorcinol. The method for manufacturing the triazine-based compound according to an embodiment of the present invention can simplify a reaction step.COPYRIGHT KIPO 2020
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Page/Page column 13; 14
(2020/03/17)
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- Synthesis, Spectra, and Theoretical Investigations of 1,3,5-Triazines Compounds as Ultraviolet Rays Absorber Based on Time-Dependent Density Functional Calculations and three-Dimensional Quantitative Structure-Property Relationship
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A series of 1,3,5-triazines were synthesized and their UV absorption properties were tested. The computational chemistry methods were used to construct quantitative structure-property relationship (QSPR), which was used to computer aided design of new 1,3,5-triazines ultraviolet rays absorber compounds. The experimental UV absorption data are in good agreement with those predicted data using the Time-dependent density functional theory (TD-DFT) [B3LYP/6–311 + G(d,p)]. A suitable forecasting model (R > 0.8, P 0.0001) was revealed. Predictive three-dimensional quantitative structure-property relationship (3D-QSPR) model was established using multifit molecular alignment rule of Sybyl program, which conclusion is consistent with the TD-DFT calculation. The exceptional photostability mechanism of such ultraviolet rays absorber compounds was studied and confirmed as principally banked upon their ability to undergo excited-state deactivation via an ultrafast excited-state proton transfer (ESIPT). The intramolecular hydrogen bond (IMHB) of 1,3,5-triazines compounds is the basis for the excited state proton transfer, which was explored by IR spectroscopy, UV spectra, structural and energetic aspects of different conformers and frontier molecular orbitals analysis.
- Wang, Xueding,Xu, Yilian,Yang, Lu,Lu, Xiang,Zou, Hao,Yang, Weiqing,Zhang, Yuanyuan,Li, Zicheng,Ma, Menglin
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p. 707 - 723
(2018/05/05)
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- A Sequential Suzuki Coupling Approach to Unsymmetrical Aryl s-Triazines from Cyanuric Chloride
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A practical approach has been developed for efficient synthesis of unsymmetrical aryl s-triazines via highly selective sequential Suzuki coupling of cyanuric chloride (2,4,6-trichlorotriazine) with aryl or vinyl boronic or diarylborinic acids catalysed by 0.1–0.5 mol% Pd(PPh3)2Cl2 under mild conditions. The second and third Suzuki couplings for unsymmetrically trisubstituted aryl s-triazines could be more practically conducted in one-pot procedure. An electron-withdrawing conjugate group at phenyl ring of arylboronic acids was unexpectedly found to completely block the coupling while steric hindrance from an ortho electron-donating substituent could be overcome. (Figure presented.).
- Wang, Chen,Zhang, Jiehui,Tang, Jie,Zou, Gang
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supporting information
p. 2514 - 2519
(2017/07/22)
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- Synthesis, Structure, Photoluminescence, and Electroluminescence of Four Europium Complexes: Fabrication of Pure Red Organic Light-Emitting Diodes from Europium Complexes
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Four new europium complexes were prepared by treating europium(III) trifluoro(thenoyl)acetonate trihydrate with new tridentate ligands, based on dipyrazolyltriazine and utilized as emitting materials in electroluminescent devices. The complexes were characterized by elemental analysis, FTIR spectroscopy, UV/Vis spectrophotometry, and 1H NMR spectroscopy. The coordinated ligands serve as light-harvesting chromophores in the complexes, with absorption maxima in the range 334–402 nm [ε = (8.9–81.4) × 103 m–1 cm–1]. The ligands efficiently sensitize europium luminescence, with maximum quantum-yield (QLEu) and observed lifetime (τobs) values of 34 % and 600 μs in the solid state and 35 % and 528 μs in toluene, respectively. The radiative lifetimes of Eu (5D0) are in the range 1170–1281 μs and the ligand-to-metal energy-transfer efficiency (ηsens) is in the range 71–92 % for those complexes in the solid state and in the range 68–97 % for those in solution. Additionally, organic light-emitting diodes (OLEDs), which exhibited pure red emission, were fabricated with europium(III) complexes. It is shown that by modifying the [Eu(tta)3·3H2O] molecule with ancillary ligands, one can tune and control its electroluminescence spectra, along with its electrical properties, such as the current/voltage characteristics of OLED devices based on [Eu(tta)3(L)]. The best OLED presented a maximum luminance of 3156 cd/m2 and a maximum efficiency of 0.7 cd/A at an applied voltage of 8 V.
- Karimi Behzad, Sara,Amini, Mostafa M.,Ghanbari, Mohammad,Janghouri, Mohammad,Anzenbacher, Pavel,Ng, Seik Weng
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p. 3644 - 3654
(2017/08/23)
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- PROCESS FOR THE PREPARATION OF TRIAZINES
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The invention relates to an improved process for the manufacture of bis-resorcinyl triazines of formula (I) wherein R1 is a C1C18alkyl group or C2-C18alkenyl group as well as the respective alkyl substituted bis-resorcinyl derivatives of formula (II) wherein R1 is a C1-C18alkyl group or C2-C18alkenyl group and R2 and R3 are independently of each other a C1-C18alkyl group or a C2-C18alkenyl group.
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Page/Page column 7-8
(2016/12/12)
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- Oxacalix[2]arene[2]triazine based ion-pair transporters
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Heteracalixaromatics are a new generation of macrocyclic hosts showing a unique structure and versatile recognition properties towards various guests. Amazingly, the application of heteracalixaromatics as membrane transporters or ion channels has never been explored. We reported herein the elaborated design of a series of oxacalix[2]arene[2]triazine-based derivatives 1-10 and their ion transport properties. Among these compounds, 3, 8-10 can mediate the transport of chloride across the lipid bilayer of EYPC with activity (EC50) ranging from 0.43 to 8.23 μM. These compounds serve as ion carriers during the transport process, and the transport activity is both anion- and cation-dependent, suggesting a Cl-/M+ ion-pair transport model. Structure-activity studies indicate that hydrogen bonding, electron deficiency of the triazine rings, lipophilicity and macrocyclic frameworks are essential for ion transport.
- Wang, Xu-Dong,Li, Sen,Ao, Yu-Fei,Wang, Qi-Qiang,Huang, Zhi-Tang,Wang, De-Xian
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supporting information
p. 330 - 334
(2015/12/30)
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- Combinatorial solid-phase synthesis of 4,6-diaryl and 4-aryl, 6-alkyl-1,3,5-triazines and their application to efficient biofuel production
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Herein we report the solid-phase synthesis of a combinatorial aryl, alkyl-triazine library and its application to biofuel production. The combination of Grignard reactions and solid supported Suzuki coupling reactions afforded unique 120 triazine compounds with high purities and minimum purification steps. Through an unbiased phenotypic screening for improved biofuel generation in oleaginous yeast, we found one diaryl triazine derivative (E4) which increased the biolipid production up to 86%.
- Kim, Jaoon Y. H.,Lee, Jae Wook,Lee, Woo Sirl,Ha, Hyung-Ho,Vendrell, Marc,Bork, Jacqueline T.,Lee, Youngsook,Chang, Young-Tae
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scheme or table
p. 395 - 398
(2012/09/05)
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- Novel orthogonal synthesis of a tagged combinatorial triazine library via grignard reaction
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To expand the diversity of 1,3,5-triazine libraries to aryl and alkyl functionalities through the CC bond, we employed a novel orthogonal synthesis via Grignard monoalkylation or monoarylation of cyanuric chloride in solution to prepare aryl- or alkyl-substituted triazine building blocks. These aryl- or alkyl-substituted triazine building blocks were captured by a resin-bound amine, followed by amination and acidic cleavage with high purity. Herein, we demonstrate a novel orthogonal synthesis of a tagged aryl- and alkyl-triazine library on solid support, utilizing building blocks prepared via Grignard reaction in solution. Through incorporation of a triethylene glycol linker at one of the alternate sites on the triazine scaffold we explored an intrinsic tagged library approach. CSIRO 2009.
- Lee, Jae Wook,Bork, Jacqueline T.,Ha, Hyung-Ho,Samanta, Animesh,Chang, Young-Tae
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experimental part
p. 1000 - 1006
(2010/03/01)
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- NOVEL 2,4,6-TRI-SUBSTITUTED HETEROCYCLES AND USES THEREOF
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Compounds of formula (I) and (II); their pharmaceutical compositions and methods of use for the treatment of neurological disorders related to amyloid ? protein production such as Alzheimer's disease.
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- Novel s-triazine compounds bearing at least one para-aminobenzalmalonic salt substituent and photoprotective cosmetic compositions comprised thereof
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Stable, topically applicable cosmetic/dermatological sunscreen compositions, well suited for the UV-photoprotection of human skin/keratinous materials, contain a thus effective amount of at least one novel s-triazine compound bearing at least one para-aminobenzalmalonic salt substituent.
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- Bis(resorcinyl)triazines useful as sunscreens in cosmetic preparations
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There are described bis(resorcinyl)triazines of the formula STR1 The compounds according to the invention are particularly suitable as sunscreens in cosmetic, pharmaceutical and veterinary medicinal preparations.
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