131468-32-1

Basic information

• Product Name: 6-chloro-N²,N⁴-bis(4-fluorophenyl)-1,3,5-triazine-2,4-diamine
• Synonyms: 6-chloro-N²,N⁴-bis(4-fluorophenyl)-1,3,5-triazine-2,4-diamine
• CAS NO: 131468-32-1
• Molecular Weight: 333.728
• Mol File: 131468-32-1.mol

Chemical Properties

• CAS DataBase Reference: 6-chloro-N²,N⁴-bis(4-fluorophenyl)-1,3,5-triazine-2,4-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-N²,N⁴-bis(4-fluorophenyl)-1,3,5-triazine-2,4-diamine(131468-32-1)
• EPA Substance Registry System: 6-chloro-N²,N⁴-bis(4-fluorophenyl)-1,3,5-triazine-2,4-diamine(131468-32-1)

Safety Data

• Hazardous Substances Data: 131468-32-1(Hazardous Substances Data)

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 371-40-4 4-fluoroaniline 
• 131468-33-2 (4,6-dichloro-[1,3,5]triazin-2-yl)-(4-fluorophenyl)-amine 

Downstream Products

• 505062-28-2 C₂₃H₁₈F₂N₆O 
• 1620172-82-8 5-(4-chloro-phenyl)-3-phenyl-4,5-dihydro-pyrazole-1-carbothioic acid [4,6-bis-(4-fluorophenylamino)-[1,3,5]triazin-2-yl]-amide 
• 1620172-81-7 5-(2-chloro-phenyl)-3-phenyl-4,5-dihydro-pyrazole-1-carbothioic acid [4,6-bis-(4-fluorophenylamino)-[1,3,5]triazin-2-yl]-amide 
• 1620172-80-6 5-(4-nitro-phenyl)-3-phenyl-4,5-dihydro-pyrazole-1-carbothioic acid [4,6-bis-(4-fluorophenylamino)-[1,3,5]triazin-2-yl]-amide 
• 1620172-79-3 3,5-diphenyl-4,5-dihydro-pyrazole-1-carbothioic acid [4,6-bis-(4-fluoro-phenylamino)-[1,3,5]triazin-2-yl]-amide 
• 1620172-78-2 3,5-diphenyl-4,5-dihydro-pyrazole-1-carbothioic acid [4,6-bis-(4-fluoro-phenylamino)-[1,3,5]triazin-2-yl]-amide 
• 1408322-22-4 C₂₈H₂₄F₂N₁₀S₂ 
• 1258254-43-1 C₂₄H₁₆F₂N₈O₂S 
• 1246834-49-0 N,N'-bis(4-fluorophenyl)-N-(pyrimidin-2-ylmethyl)-1,3,5-triazine-2,4,6-triamine 

Relevant articles and documents

Triaminotriazine DNA helicase inhibitors with antibacterial activity

Screening of a chemical library in a DNA helicase assay involving the Pseudomonas aeruginosa DnaB helicase provided a triaminotriazine inhibitor with good antibacterial activity but associated cytotoxicity toward mammalian cells. Synthesis of analogs provided a few inhibitors that retained antibacterial activity and demonstrated a significant reduction in cytotoxicity. The impact of serum and initial investigations toward a mode of action highlight several features of this class of compounds as antibacterials.

Design, synthesis, anticancer, antibacterial, and antifungal evaluation of 4-aminoquinoline-1,3,5-triazine derivatives

A series of 4-aminoquinoline 1,3,5-triazine derivatives were synthesized and evaluated for anticancer activity against cancer cell lines HeLa, MCF-7, HL-60, HepG2 where these derivatives exert significant anticancer activity. The molecules found nontoxic against MCF-12A. The molecules also showed potent inhibition of EGFR-TK as compared to eroltinib in enzyme-based assay. The newly synthesized derivatives were screened for their in vitro antibacterial and antifungal activity against Bacillus subtilis, Bacillus cereus, Staphylococcus aureus, Proteus vulgaris, Escherichia coli, Pseudomonas aeruginosa and Candida albicans, Aspergillus niger, Aspergillus fumigatus using cefixime and fluconazole as standard. Antibacterial screening results suggest that compound 7c showed potent activity against S. aureus, P. aeruginosa, and P. vulgaris. In antifungal screening, compound 7b showed significant activity against A. niger, A. fumigatus and moderate activity against C. albicans.

Optimization of the pharmacokinetic properties of potent anti-trypanosomal triazine derivatives

Human African trypanosomiasis is causing thousands of deaths every year in the rural areas of sub-saharan Africa. There is a high unmet medical need since the approved drugs are poorly efficacious, show considerable toxicity and are not easy to administer

Discovery of novel 1,3,5-triazine-thiazolidine-2,4-diones as dipeptidyl peptidase-4 inhibitors with antibacterial activity targeting the S1 pocket for the treatment of type 2 diabetes

A novel series of 1,3,5-triazine-thiazolidine-2,4-diones was synthesized and characterized by a number of analytical and spectroscopic techniques. The molecules were screened for the in vitro inhibition of dipeptidyl peptidase-4 and compound 7a showed the most prominent inhibition with IC50 = 6.25 μM. The other compounds showed considerable inhibition (IC50 = 12.11-49.21 μM). Docking studies indicated that the lipophilic thiazolidine-2,4-dione fragment of ligand 7a was oriented towards the tight lipophilic cavity of the S1 pocket of the active site formed by residues such as Tyr631, Val656, Trp659, Tyr662, Tyr666 and Val711 via the formation of H-bonds with Tyr547. One of the amines present on the wings of the triazine formed a hydrogen bond with Glu205, a vital residue for the N-terminal recognition site with an efficient CDOCKER interaction energy. In a bacterial inhibition study, the entire set of compounds showed excellent activity and, in some instances, were found to be equipotent to the cefixime used as a standard.

Structure-guided discovery of 1,3,5-triazine-pyrazole conjugates as antibacterial and antibiofilm agent against pathogens causing human diseases with favorable metabolic fate

Impressed by the exceptional antibacterial activity exhibited by our earlier designed molecules originating from 1,3,5-triazine, the present study was undertaken to synthesize a novel series of 1,3,5-triazine-pyrazole conjugates to bring diversity around the core skeleton. The target analogues showed potent antibacterial activity against tested Gram-positive and Gram-negative microorganisms. The toxicity and metabolic site prediction studies were also held out to set an effective lead candidate for the future antibacterial drug discovery initiatives.

Design and one-pot synthesis of hybrid thiazolidin-4-one-1,3,5-triazines as potent antibacterial agents against human disease-causing pathogens

An efficient and general one-pot reaction to a novel series of hybrid thiazolidine-4-one-1,3,5-triazine derivatives was developed. The easy work-up of the products, rapid reaction, and mild conditions are notable features of this protocol. These molecules were found to exhibit potent activity against a panel of Gram-positive and Gram-negative micro-organisms.

Design, Facile Synthesis, and Antibacterial Activity of Hybrid 1,3,4-thiadiazole-1,3,5-triazine Derivatives Tethered via -S- Bridge

Some hybrid 1,3,4-thiadiazole-1,3,5-triazine derivatives tethered via -S- bridge were synthesized and characterized with the aid of spectroscopic and elemental analysis. These hybrid conjugates were then investigated for their antibacterial activity against selected Gram-positive and Gram-negative bacteria. Excellent to moderate antibacterial activity was presented by the target compounds.

COMPOUNDS WITH DDX3 INHIBITORY ACTIVITY AND USES THEREOF

The present invention relates to the medical use of the compound of formula 1,2,3 or 4

Toward the Discovery of Novel Anti-HIV Drugs. Second-Generation Inhibitors of the Cellular ATPase DDX3 with Improved Anti-HIV Activity: Synthesis, Structure-Activity Relationship Analysis, Cytotoxicity Studies, and Target Validation

A hit optimization protocol applied to the first nonnucleoside inhibitor of the ATPase activity of human DEAD-box RNA helicase DDX3 led to the design and synthesis of second-generation rhodanine derivatives with better inhibitory activity toward cellular DDX3 and HIV-1 replication. Additional DDX3 inhibitors were identified among triazine compounds. Biological data were rationalized in terms of structure-activity relationships and docking simulations. Antiviral activity and cytotoxicity of selected DDX3 inhibitors are reported and discussed. A thorough analysis confirmed human DDX3 as a valid anti-HIV target. The compounds described herein represent a significant advance in the pursuit of novel drugs that target HIV-1 host cofactors.

Synthesis and antibacterial evaluation of series of novel tri-substituted-s-triazine derivatives

Two novel series of s-triazine derivatives (6a-e and 7a-f) were synthesized with various aromatic and heterocyclic amines. The synthesized compounds were subsequently evaluated for their in vitro antibacterial activity against three gram-positive viz. Bacillus subtilis (NCIM- 2063), Bacillus cereus (NCIM-2156), Staphylococcus aureus (NCIM-2079) and gram-negative bacteria viz. Pseudomonas aeruginosa (NCIM-2036), Escherichia coli (NCIM-2065) and Klebseilla pneumoniae (NCIM-2706) by the broth dilution method as recommended by the National Committee for Clinical Laboratory Standards (NCCLS) using streptomycin as reference standard. Structures of the synthesized compounds were elucidated on the basis of elemental analyses and spectral data. Springer Science+Business Media, LLC 2010.