21665-49-6

Upstream product

• 110-91-8 morpholine 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 62-53-3 aniline 
• 6601-22-5 2,6-Dichloro-4-morpholino-1,3,5-triazine 
• 2272-40-4 2-phenylamino-4,6-dichloro-s-triazine 

Downstream Products

• 21665-50-9 (4-morpholin-4-yl-6-piperazin-1-yl-[1,3,5]triazin-2-yl)-phenyl-amine 
• 1454694-92-8 C₂₄H₂₅ClN₈O 
• 1454694-97-3 C₂₅H₂₇ClN₈O 
• 1454695-07-8 C₂₆H₂₉ClN₈O 
• 1584056-14-3 2-N-{2-[bis(2-{10β-dihydroartemisinoxy}ethyl)amino]ethyl}-6-(morpholin-4-yl)-4-N-phenyl-1,3,5-triazine-2,4-diamine 
• 139191-20-1 2-N-(2-aminoethyl)-6-(morpholin-4-yl)-4-N-phenyl-1,3,5-triazine-2,4-diamine 

Relevant academic research and scientific papers

Design and development of novel thiazolidin-4-one-1,3,5-triazine derivatives as neuro-protective agent against cerebral ischemia–reperfusion injury in mice via attenuation of NF-?B

The present study enumerates the discovery and development of novel thiazolidin-4-one-1,3,5-triazine as neuro-protective agent against cerebral ischemia–reperfusion injury in mice. These compounds showed significant inhibition of NF-?B transcriptional activity in LPS-stimulated RAW264.7 cells, displaying compound 8k as most potent inhibitor among the tested derivative. The compound 8k was further studied in in vivo middle cerebral artery occlusion (MCAO) mice model for neuro-protective action. Results suggest that compound 8k causes attenuation of inflammation (TNF-α, IL-β, and IL-6), oxidative stress (SOD, GSH, and MDA), and apoptosis (Bcl-2, Bax, and cleaved caspase-3) in MCAO mice in concentration-dependent manner. Collectively, our results documented that compound 8k pre-treatment protects cerebral I/R. This novel lead scaffold may be helpful for investigation of new neuro-protective agent by inactivation of NF-?B.

Synthesis, X-ray crystal structures, and preliminary antiproliferative activities of new s-triazine-hydroxybenzylidene hydrazone derivatives

We herein report a new small library of Schiff-base compounds that encompasses s-triazine and (2 or 4)-hydroxylbenzylidene derivatives. These compounds were synthesized through a hydrazone linkage connecting both the s-triazine and hydroxybenzylidene deri

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.

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.

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, in vitro antiplasmodial activity and cytotoxicity of a series of artemisinin-triazine hybrids and hybrid-dimers

A series of artemisinin-triazine hybrids and hybrid-dimers were synthesized and their in vitro antimalarial activity against the chloroquine sensitive (CQS), the gametocytocidal (NF54) and the choroquine resistant (CQR) Dd2 strains of Plasmodium falciparu

Anticancer activity of 4-aminoquinoline-triazine based molecular hybrids

In this study the potential for anticancer activity of 4-aminoquinoline- triazine based hybrids has been investigated on 60 human cancer cell lines (NCI 60). The representative compounds show activity on a range of cell lines and apoptosis as the mode of growth inhibition. The Royal Society of Chemistry 2014.

4-aminoquinoline-triazine-based hybrids with improved in vitro antimalarial activity against CQ-sensitive and CQ-resistant strains of plasmodium falciparum

A systematic chemical modification in the triazine moiety covalently attached via suitable linkers to 4-amino-7-chloroquinolines yielded a series of new 7-chloro-4-aminoquinoline-triazine hybrids exhibiting high in vitro activity against W2 (chloroquine-resistant) and D6 (chloroquine-sensitive) strains of Plasmodium falciparum without any toxicity against mammalian cell lines (Vero, LLC-PK11, HepG2). Many of the compounds (6, 8, 10, 11, 13, 14, 16, 27, 29 and 33) showed excellent potency against chloroquine sensitive and resistant strains. In particular, compounds 6, 8, 14, 16 and 29 were found to be significantly more active than chloroquine against the chloroquine-resistant strains (W2 clone) of P. falciparum.

Discovery of new 1,3,5-triazine scaffolds with potent activityagainst Mycobacterium tuberculosis H37Rv

A series of eighty one 2,4,6-trisubstituted-1,3,5-triazines were synthesized and evaluated in vitro for the growth inhibition of Mycobacterium tuberculosis H37Rv. Fifteen compounds from this series exhibited good to moderate activity with an MIC in the ra

Synthesis and bioevaluation of hybrid 4-aminoquinoline triazines as a new class of antimalarial agents

The emergence and rapid spread of chloroquine resistant strains of Plasmodium falciparum has dramatically reduced the chemotherapeutic options. Towards this goal, a series of new class of hybrid 4-aminoquinoline triazines were synthesized and screened aga