30369-82-5

Usage

Uses

Used in Pharmaceutical Industry:
CHEMBRDG-BB 5106991 is used as a potential therapeutic agent for the treatment of disorders related to dopamine and serotonin neurotransmission. Its interaction with these receptors makes it a candidate for addressing conditions such as mood disorders, psychosis, and movement disorders.
Given the compound's classification and potential applications, further research is essential to elucidate its pharmacological properties and establish its safety and efficacy in medical use. This would involve detailed studies on its mechanism of action, pharmacokinetics, and potential side effects, as well as clinical trials to confirm its therapeutic value in treating the targeted conditions.

InChI:InChI=1/C10H8Cl2N4/c11-8-14-9(12)16-10(15-8)13-6-7-4-2-1-3-5-7/h1-5H,6H2,(H,13,14,15,16)

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 100-46-9 benzylamine 

Downstream Products

• 92297-31-9 benzyl-(bis-aziridin-1-yl-[1,3,5]triazin-2-yl)-amine 
• 189250-15-5 N-benzyl-6-chloro-[1,3,5]triazine-2,4-diamine 
• 868599-64-8 dimethyl 11,11'-{[6-(benzylamino)-1,3,5-triazine-2,4-diyl]diimino}diundecanoate 
• 51304-99-5 C₁₈H₂₄N₆O₂ 
• 1394122-43-0 C₂₆H₃₀F₃N₇O₂S 

Relevant academic research and scientific papers

Trisubstituted 1,3,5-Triazines: The First Ligands of the sY12-Binding Pocket on Chemokine CXCL12

CXCL12, a CXC-type chemokine, binds its receptor CXCR4, and the resulting signaling cascade is essential during development and subsequently in immune function. Pathologically, the CXCL12-CXCR4 signaling axis is involved in many cancers and inflammatory diseases and thus has sparked continued interest in the development of therapeutics. Small molecules targeting CXCR4 have had mixed results in clinical trials. Alternatively, small molecules targeting the chemokine instead of the receptor provide a largely unexplored space for therapeutic development. Here we report that trisubstituted 1,3,5-triazines are competent ligands for the sY12-binding pocket of CXCL12. The initial hit was optimized to be more synthetically tractable. Fifty unique triazines were synthesized, and the structure-activity relationship was probed. Using computational modeling, we suggest key structural interactions that are responsible for ligand-chemokine binding. The lipophilic ligand efficiency was improved, resulting in more soluble, drug-like molecules with chemical handles for future development and structural studies.

Exploring the influence of designer surfactant hydrophobicity in key C–C/C–N bond forming reactions

Designer micellar medium was explored for the transformation of diverse anilines to the corresponding densely substituted biologically relevant skatole derivatives in an aqueous medium via 5-exo-trig cyclization reaction. The scope of the reaction was extended to intermolecular Csp2-Csp2 and Csp2-N bond forming reactions in water. Systematic investigations revealed that altering hydrophobicity of surfactant influences the yield of both C–C and C–N bond forming reactions in water.

Design and synthesis of mono-and di-pyrazolyl-s-triazine derivatives, their anticancer profile in human cancer cell lines, and in vivo toxicity in zebrafish embryos

s-Triazine is considered a privileged structure, as it is found in several FDA-approved drugs. In the framework of our ongoing medicinal chemistry project based on the use of s-triazine as a scaffold, we synthesized a series of mono- and di-pyrazolyl-s-triazine derivatives and tested them against four human cancer cell lines, namely Human breast carcinoma (MCF 7 and MDA-MB-231), hepatocellular carcinoma (HepG2), colorectal carcinoma (LoVo), and leukemia (K562). The cell viability assay revealed that most of the s-triazine compounds induced cytotoxicity in all four types of human cancer cell lines, however, compounds 4a, and 6g, both of them have a piperidine moiety in their structure were most effective. These two compounds affected the cell viability of cancer cells, with IC50 values within the range between 5 to 9 μM. The cell cycle analysis showed that 4a and 6g induced S and G2/M phase cell cycle arrest in K562 cells. This could be the mechanism by which these molecules induced cytotoxicity in tested cancer cells. The prepared compounds were tested in zebrafish embryos to evaluate in vivo and developmental toxicity of the pyrazolyl-s-triazine derivatives in animals. None of the derivatives were lethal in the concentration range tested.

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.

Tailoring the Substitution Pattern on 1,3,5-Triazine for Targeting Cyclooxygenase-2: Discovery and Structure-Activity Relationship of Triazine-4-Aminophenylmorpholin-3-one Hybrids that Reverse Algesia and Inflammation in Swiss Albino Mice

Here, we report analgesic and anti-inflammatory activity of a series of compounds obtained by appending 4-aminophenylmorpholin-3-one and acyclic, cyclic, or heterocyclic moieties on 1,3,5-triazine. The structures of compounds 4b and 6b are optimized for the best inhibition of COX-2 with IC50 values of 0.06 and 0.08 μM, respectively, and selectivity over COX-1 of 166 and >125, respectively. At the dose of 5 mg kg-1, these compounds significantly reduced acetic acid induced writhings, and their ED50 values were found to be 2.2 and 1.9 mg kg-1, respectively. Besides the cell-based and animal-based experiments showing the modes of action of these compounds targeting COX-2, the interaction behavior of 4b with COX-2 was also characterized, with physicochemical experiments including ITC, NMR, UV-vis, and molecular-modeling studies. Characteristically, these compounds interact with R120, Y355, and W385, the residues responsible for holding the substrate and mediating the process of electron transfer during the metabolic phase of the enzyme.

Novel pyrazolyl-s-triazine derivatives, molecular structure and antimicrobial activity

A new series of pyrazole-containing s-triazine derivatives were synthesized by reaction of the corresponding s-triazinyl hydrazine derivatives with acetylacetone in the presence of HClO4 or DMF/TEA. The former method allowed the preparation of the target products with higher yields. All compounds were fully characterized. X-ray single crystal diffraction for two representative compounds (4-(4,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,3,5-triazin-2-yl)morpholine and N-benzyl-4-(3,5-dimethyl-1H-pyrazol-1-yl)-6-(piperidin-1-yl)-1,3,5-triazin-2-amine) was studied and the molecular structures were optimized using the DFT/B3LYP method. The structures were found to be in agreement with X-ray structures. The antimicrobial and antifungal activity of the prepared compounds were tested against the growth of several microorganisms.

Synthesis and Biological Evaluation of Amidinourea and Triazine Congeners as Inhibitors of MDA-MB-231 Human Breast Cancer Cell Proliferation

A series of novel amidinourea derivatives was synthesized, and the compounds were evaluated as inhibitors of MDA-MB-231 human breast cancer cell proliferation. In addition, a second series of triazine derivatives designed as rigid congeners of the amidinoureas was synthesized, and the compounds were evaluated for their antiproliferative activity. Among the two series, amidinourea 3 d (N-[N-[8-[[N-(morpholine-4-carbonyl)carbamimidoyl]amino]octyl]carbamimidoyl]morpholine-4-carboxamide) emerged as a potent anticancer hit compound with an IC50value of 0.76 μm, similar to that of tamoxifen.

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.

Synthesis and characterization of new s-triazine bearing benzimidazole and benzothiazole derivatives as anticancer agents

Two new series of s-triazine derivatives appended with benzimidazole (15a-h) and benzothiazole derivatives (16a-h) are synthesized, and structure-activity relationships on anticancer activity of these 15a-h and 16a-h were probed. In vitro inhibitory activity against the growth of six cancer cell lines, viz., MCF-7, MDAMB-231, PC-3, DU-145, HT-29 and HGC-27 was evaluated for synthesized analogues. Among the two series of compounds, derivatives containing benzimidazole scaffold were found to be relatively potent over benzothiazole analogues. In accordance with our previous observation, within benzimidazole derivatives, tri-substituted s-triazine derivatives were found to be more potent over di-substituted derivatives irrespective of cell lines. Structure-activity relationships provided useful insights into these classes of compounds and paved the way to design novel analogues with more potency.

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.