30369-87-0

Usage

InChI:InChI=1/C10H8Cl2N4O/c1-17-7-5-3-2-4-6(7)13-10-15-8(11)14-9(12)16-10/h2-5H,1H3,(H,13,14,15,16)

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 90-04-0 2-methoxy-phenylamine 
• 754207-98-2 2,4-dichloro-6-[N-(4'-ethoxyphenyl)dithiocarbamoyl]-s-triazine 

Downstream Products

• 117488-28-5 2-(2'-methoxyanilino)-4-(benzamido-2'-yloxy)-6-chloro-s-triazine 
• 117488-29-6 2-(2'-methoxyanilino)-4-(benzamido-2'-yloxy)-6-(phenylureido)-s-triazine 
• 841281-90-1 2-chloro-4-(4-tert-butoxycarbonylpiperazin-1-yl)-6-(2-methoxyphenylamino)-1,3,5-triazine 
• 1084910-34-8 C₂₆H₂₄N₆OS₄ 
• 1356492-57-3 4-[4-ethylamino-6-(2-methoxy-phenylamino)-[1,3,5]triazin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester 
• 1356536-66-7 6-[4-(2-dimethylamino-ethyl)-piperazin-1-yl]-N-ethyl-N'-(2-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine 
• 1356536-67-8 6-[4-(2-dimethylamino-ethyl)-piperazin-1-yl]-N-isopropyl-N'-(2-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine 
• 1356492-50-6 6-chloro-N-isopropyl-N'-(2-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine 

Relevant academic research and scientific papers

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

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.

Heterocyclic compounds as well as preparation method and application thereof

The invention belongs to the field of medicines and particularly relates to heterocyclic compounds with the structural characteristics shown in formula (I) or pharmaceutically acceptable salts, a preparation method and an application of the heterocyclic compounds as a nucleotide oxidative damage repairase MTH1 inhibitor. Pharmacological experiment results indicate that the compounds have significant inhabitation effects on the activity of MTH1 and can be used for preventing and treating clinical diseases related to MTH1.

Docking, synthesis and antimalarial activity of novel 4-anilinoquinoline derivatives

A series of 4-anilinoquinoline triazine derivatives were designed, synthesized and screened for in vivo antimalarial activity against a chloroquine-sensitive strain of Plasmodium berghei. The compounds were further subjected to in vitro antimalarial activity against chloroquine-resistant W2 strain of Plasmodium falciparum and β-haematin inhibition studies. All the compounds exhibited in vivo antimalarial activity better than that shown by the standard drug, chloroquine. Twelve out of fifteen compounds showed better inhibition than that of chloroquine against chloroquine-resistant W2 strain of Plasmodium falciparum. Ten compounds showed β-haematin inhibition, better than that of chloroquine, with IC50 values in the range of 18–25?μM. One compound, 3k, was found to be better than artemisinin against W2 strain of Plasmodium falciparum and also displayed the best β-haematin inhibitory activity, thereby becoming eligible to be explored as a potential lead for antimalarial chemotherapy.

Triazine compound as well as preparation method and application thereof

The invention provides a triazine compound shown as a chemical formula (I) and a preparation method thereof as well as an application of the triazine compound in preparing drugs for treating central nervous system diseases. In the formula, R1 is selected

Design, synthesis, and cytotoxicity of novel 2,4,6-trisubstituted 1,3,5-triazines bearing aryl hydrazone moiety as potent antitumor agent

A novel series of 2,4,6-trisubstituted 1,3,5-triazine derivatives bearing aryl hydrazone moiety were designed and synthesized under the guidance of scaffold hopping and bioisosterism from the autophagy inhibitor VLX600. The target compounds were evaluated for cytotoxicity against HT-29 by MTT assay with VLX600 as positive control. Then, ten potent target compounds (5c-5f, 5i-5r, 5s, 5t) were further evaluated against two cancer cell lines H460 and A549 and one normal cell line WI-38. Most of them exhibited significant cytotoxicity against one or more cell lines. Particularly, a promising compound 5f was identified, which exhibited the most potent cytotoxicity against HT-29, H460 and A549 cancer cell lines with IC50 values of 0.047 μM, 0.071 μM and 0.071 μM, respectively, which was 10-to 62-folds more potent than VLX600 (IC50 = 0.47 μM, 4.1 μM, 4.4 μM). The preliminary structure-activity relationships (SARs) of the compounds were also discussed.

Synthesis and structure-activity relationship study of triazine-based inhibitors of the DNA binding of NF-κB

Nuclear transcription factor nuclear factor-kappa B (NF-κB) has diverse pathophysiological functions, and NF-κ B inhibitors are considered to be candidates for multiple therapeutic applications. We previously reported a novel triazine-based NF-κB inhibitor, 2-anilino-4,6-dichloro-1,3,5- triazine (NI241), that directly inhibits DNA binding of NF-κB. Here, we report synthesis of a series of triazine derivatives and evaluation of their structure-activity relationships for NF-κB inhibition. We found that 2-amino-4,6-dichloro-1,3,5-triazine substructure is essential for the inhibitory activity of the lead compound NI241, and modification of NI241 by introduction of an m-methoxy substituent on the phenyl ring afforded the more potent derivative 28. The structure-activity relationships identified in this study suggested a possible mechanism of irreversible NF-κB inhibition by NI241, and should be helpful in the design of other NF-κB inhibitors.

Elaborate ligand-based modeling and subsequent synthetic exploration unveil new nanomolar Ca2+/calmodulin-dependent protein kinase II inhibitory leads

Ca2+/calmodulin-dependent protein kinase II (CaMKII) has been recently implicated in cardiovascular diseases and hypertension prompting several attempts to discover and optimize new CaMKIIδ inhibitors. Towards this end we explored the pharmacophoric space of 88 CaMKIIδ inhibitors using nine diverse sets of inhibitors to identify high quality pharmacophores. Subsequently, genetic algorithm and multiple linear regression analysis were employed to select an optimal combination of pharmacophoric models and 2D physicochemical descriptors capable of accessing self-consistent quantitative structure-activity relationship (QSAR) of optimal predictive potential (r722=0.70, F = 18.19, rLOO2=0.71, rPRESS2 against 16 external test inhibitors = 0.60). Three orthogonal pharmacophores emerged in the QSAR equation suggesting the existence of at least three binding modes accessible to ligands within CaMKIIδ binding pocket. Receiver operating characteristic (ROC) curves analysis established the validity of QSAR-selected pharmacophores. We employed the pharmacophoric models and associated QSAR equation to screen the national cancer institute (NCI) list of compounds. In silico screening identified nanomolar and low micromolar inhibitors. The most potent hits exhibited IC 50 values of 20 and 82 nM. The best pharmacophoric model (Hypo8/31) was employed to guide the synthesis of novel triazine-based CaMKIIδ inhibitors, of which the most potent illustrated an IC50 value of 154 nM against CaMKIIδ.

Simple and efficient synthetic routes to bioactive s-triazinyl dithiocarbamate derivatives

Series of 2,4-diarylamino-6-[N-(3′-methylphenyl)dithiocarbamoyl]-s- triazines (4a-l) and 2,4-bis[N-(3′-methylphenyl)dithiocarbamoyl]-6- arylamino-s-triazines (7a-l) were synthesized by two different synthetic routes. In the first route (A), 2,4,6-tricholoro-s-triazine (1) was condensed with N-(3-methylphenyl)ammoniumdithiocarbamate to afford compounds 3 or 6, which on reaction with different aryl amines afforded compounds 4a-l or 7a-l. In the second route (B), condensation of 1 with different aryl amines yielded compounds 2a-l or 5a-l. On further treatment with N-(3-methylphenyl) ammoniumdithiocarbamate these afforded compounds 4a-l or 7a-l. The newly synthesized compounds 4a-l and 7a-l were characterized by elemental analyses, infrared (IR), and 1H nuclear magnetic resonance (NMR) spectroscopic investigation. All the products were evaluated for their antibacterial and antifungal activity.

N4-Phenyl modifications of N2-(2-hydroxyl)ethyl-6-(pyrrolidin-1-yl)-1,3,5-triazine-2,4-d iamines enhance glucocerebrosidase inhibition by small molecules with potential as chemical chaperones for Gaucher disease

A series of 1,3,5-triazine-2,4,6-triamines were prepared and analyzed as inhibitors of glucocerebrosidase. Synthesis, structure activity relationships and the selectivity of chosen analogues against related sugar hydrolases enzymes are described.

2-CYANO-1,3,5-TRIAZINE-4,6-DIAMINE DERIVATIVES

The invention relates to the use of a 2-cyano-1,3,5-triazine -4,6-diamine derivative having general formula (I), wherein R1 is (C1-6)alkyl, (C3-8)cycloalkyl, aryl, aryl(C1-4)alkyl, aryloxy(C1-4)alkyl, heteroaryl or heteroaryloxy(C1-4)alkyl; R2 is H or (C1-4)alkyl; or R1 and R2 together with the nitrogen to which they are bound form a 4-8 membered heterocyclic ring, optionally further comprising 1 or more heteroatoms selected from O, S or NR5, which ring may be substituted with (C1-4)alkyl, (C3-8)cycloalkyl, aryl, aryl(C1-4)alkyl or NR6R7,and which ring may be fused to a benzene ring; R3 is (C1-6)alkyl, (C3-8) cycloalkyl (optionally comprising 1 or more heteroatoms selected from O, S or NR8), aryl, aryl(C1-4)alkyl or heteroaryl; R4 is H or (C1-4)alkyl; or R3 and R4 together with the nitrogen to which they are bound form a 4-8 membered heterocyclic ring, optionally further comprising 1 or more heteroatoms selected from O, S or NR9; R5, R8 and R9 are independently H, (C1-4)alkyl, (C3-8) cycloalkyl, aryl or aryl(C1-4)alkyl; R6 and R7 are independently H or (C1-4)alkyl; or R6 and R7 form together with the nitrogen to which they are bound a 4-8 membered heterocyclic ring; or a pharmaceutically acceptable salt thereof, for the preparation of a medicament for the treatment of osteoporosis and atherosclerosis.