Synthesis and antimicrobial activity of N1-benzyl or N1-benzyloxy-1,6-dihydro-1,3,5-triazine-2,4-diamines

Ma, Xiang; Tan, Soo-Tong; Khoo, Chai-Ling; Sim, Hong-May; Chan, Lai Wah; Chui, Wai Keung

doi:10.1016/j.bmcl.2011.06.125

Cited by 25 publications

(9 citation statements)

References 14 publications

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“…Nevertheless, this expedited route to 13a was not undesirable, since the dihydrotriazine core is known to display antiparasitic and antimicrobial activity. 20 …”

Section: Resultsmentioning

confidence: 99%

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

et al. 2014

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A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first in class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles.

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“…Nevertheless, this expedited route to 13a was not undesirable, since the dihydrotriazine core is known to display antiparasitic and antimicrobial activity. 20 …”

Section: Resultsmentioning

confidence: 99%

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

et al. 2014

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“…1,3,5-Triazine (s-triazine) is one of the most fascinating chemical cores in medicinal chemistry applications due to the broad range of biological activities such as anti-microbial [ 5 ], antifungal [ 6 ], antimalarial [ 7 ], carbonic anhydrase inhibitors [ 8 , 9 , 10 , 11 , 12 ] and anti-cancer agents [ 13 , 14 , 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anti-proliferative Activity, and Molecular Docking Study of New Series of 1,3-5-Triazine Schiff Base Derivatives

et al. 2020

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Based on the use of s-triazine as a scaffold, we report here a new series of s-triazine Schiff base derivatives and their anti-proliferative activity against two cancer cell lines: human breast carcinoma (MCF-7), and colon cancer (HCT-116) compared with tamoxifen as a reference compound. Several derivatives exhibited growth inhibition activity in the sub-micromolar range. The results reveal that the s-triazine Schiff base derivatives showed varied activities and that the substituents on the s-triazine core have a great effect on the anti-proliferative activity. Compounds with a piperidino and benzylamino substituent on the s-triazine moiety 4b and 4c were most effective in both cell lines compared to the reference compound used. In addition, compound 4b has a para chlorine atom on the benzylidine residue, demonstrating the most potent activity with IC50 values of 3.29 and 3.64 µM in MCF-7 and HCT-116, respectively. These results indicate that in general, the nature of the substituents on the triazine core and the type of substituent on the benzilyldene ring significantly influenced the anti-proliferative activity. The results obtained from the anti-proliferative activity and the molecular docking study indicate that s-triazine-hydrazone derivatives may be an excellent scaffold for the development of new anti-cancer agents.

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“…The family of triazines is of considerable interest in fields related to organic and medicinal chemistry. 2,4-Diaminotriazines are privileged scaffolds exhibiting diverse biological activities such as antibacterial [ 1 ], anti-HSV-1 [ 2 ], antitumor [ 3 ], anti-HIV [ 4 ], inhibitor of Trypanosoma brucei [ 5 ], angiogenesis inhibitor [ 6 ], antiplasmodial antifolates [ 7 ], and antimicrobial [ 8 ]. Moreover, and in particular N 2 ,6-disubstituted-1,3,5-triazine-2,4-diamines possess a wide range of chemotherapeutic activities [ 8 – 11 ].…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted efficient one-pot synthesis of N²-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

Moustafa

Mekheimer

Al‐Mousawi

et al. 2020

Beilstein J. Org. Chem.

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Synthesis and antimicrobial activity of N1-benzyl or N1-benzyloxy-1,6-dihydro-1,3,5-triazine-2,4-diamines

Cited by 25 publications

References 14 publications

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

Synthesis, Anti-proliferative Activity, and Molecular Docking Study of New Series of 1,3-5-Triazine Schiff Base Derivatives

Microwave-assisted efficient one-pot synthesis of N²-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

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Synthesis and antimicrobial activity of N1-benzyl or N1-benzyloxy-1,6-dihydro-1,3,5-triazine-2,4-diamines

Cited by 25 publications

References 14 publications

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

Synthesis, Anti-proliferative Activity, and Molecular Docking Study of New Series of 1,3-5-Triazine Schiff Base Derivatives

Microwave-assisted efficient one-pot synthesis of N2-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

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Microwave-assisted efficient one-pot synthesis of N²-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines