1,2,3-Triazine Scaffold as a Potent Biologically Active Moiety: A Mini Review

Kumar, Rakesh; Singh, Amar Deep; Singh, Jitendra; Singh, Hariram; Roy, Ranjit; Chaudhary, Anurag

doi:10.2174/1389557513666140103111017

Cited by 41 publications

(22 citation statements)

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“…1,3,5-Triazine or s-triazine belongs to the group of heterocyclic compounds having significant applications within pharmaceuticals, textile, rubber, and plastics industries, and as polymer photostabilizers, herbicides, dyestuffs, optical bleaches, explosives, and surface active agents [1,2]. Several derivatives of s-triazine have exhibited antimicrobial [3], antibacterial [4], antifungal [3], anti-HIV [5], anticancer [6,7], and a wide range of other biological activities [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

Sharma

Jad

Siddiqui

et al. 2017

Journal of Chemistry

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1,3,5-Triazines and pyrimidine-2,4,6-triones belong to that class of compounds which are well known in literature for possessing wide range of biological activities. Here, we report a new family of compounds that encompasses these two structures. The union of both heterocycles was carried out through a hydrazone moiety incorporated into an acetyl group at the position 5 of 1,3-dimethyl pyrimidine derivative. The synthetic strategy adopted allowed the preparation of the target compounds with excellent yields and good purities. The synthesized compounds were well characterized by NMR (1H and 13C), HRMS, and elemental analysis. Furthermore, the tautomerism of enhydrazine versus hydrazone has also been studied.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

Sharma

Jad

Siddiqui

et al. 2017

Journal of Chemistry

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“…The triazine moiety presents an exciting biological profile in the rational development of various hybrid pharmaceuticals for targeting the diseased conditions and the related complicacies therein (Singla, Luxami, & Paul, 2015a; Singla, Luxami, & Paul, 2015b). The conjugation of 1,3,5‐triazine nucleus with biologically privileged moieties delivers synergistic therapeutic effects combining the intrinsic potencies of the parent fragments (Kumar et al, 2014; Kumar, Khan, Ponnan, & Rawat, 2014). In this review, we present the therapeutic implications of 1,3,5‐triazine nucleus hybridized with various bioactive fragments in the rational designing of novel drug molecules for targeting the challenging diseases or diseased conditions.…”

Section: Introductionmentioning

confidence: 99%

Hybrid molecules based on 1,3,5‐triazine as potential therapeutics: A focused review

Prasher

Sharma

Aljabali

et al. 2020

Drug Development Research

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Majority of the representative drugs customarily interact with multiple targets manifesting unintended side effects. In addition, drug resistance and over expression of the cellular efflux‐pumps render certain classes of drugs ineffective. With only a few innovative formulations in development, it is necessary to identify pharmacophores and novel strategies for creating new drugs. The conjugation of dissimilar pharmacophoric moieties to design hybrid molecules with an attractive therapeutic profile is an emerging paradigm in the contemporary drug development regime. The recent decade witnessed the remarkable biological potential of 1,3,5‐triazine framework in the development of various chemotherapeutics. The appending of the 1,3,5‐triazine nucleus to biologically relevant moieties has delivered exciting results. The present review focuses on 1,3,5‐triazine based hybrid molecules in the development of pharmaceuticals.

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“…The 1,2,3-triazinone ring is an important biophore fragment for the creation of new promising antimicrobial agents based on the 9,10-anthraquinone platform. This pharmacophore is a structural component of many natural and synthetic biologically active compounds with various therapeutic effects [18,19]. The compounds with a sedative, diuretic, anesthetic, antiarthritic, antitumor, antibacterial, antifungal, antituberculosis, antiviral, antiinflammatory, antihistamine activity were found among 1,2,3-triazine derivatives connected with various carbo-and heterocyclic fragments [20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones as a New Class of Antistaphylococcal Agents: Synthesis and Biological Evaluation

et al. 2019

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The development and spread of resistance of human pathogenic bacteria to the action of commonly used antibacterial drugs is one of the key problems in modern medicine. One of the especially dangerous and easily developing antibiotic resistant bacterial species is Staphylococcus aureus. Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones 22–38 have been developed as novel effective antistaphylococcal agents. These compounds have been obtained by sequential conversion of 1-amino-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (1) and 1-amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (2) into the corresponding amides 5–21, followed by subsequent endo-cyclization under the influence of sodium nitrite in acetic acid. Evaluation of the antimicrobial activity of the synthesized compounds against selected species of Gram-positive and Gram-negative bacteria as well as pathogenic yeasts of the Candida genus has been carried out by the serial dilution method. It has been established that anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones exhibit selective antibacterial activity against Gram-positive bacteria. Eight, six and seven, out of seventeen compounds tested, effectively inhibited the growth of S. aureus ATCC 25923, S. aureus ATCC 29213 and S. epidermidis ATCC12228, respectively, at a concentration equal to 1 µg/mL or lower. The high antistaphylococcal potential of the most active compounds has been also confirmed against clinical isolates of S. aureus, including the MRSA strains. However, bacteria of the Staphylococcus genus have demonstrated apparent resistance to the novel compounds when grown as a biofilm. None of the four selected compounds 3234 and 36 at a concentration of 64 µg/mL (128 or 256 × MIC—against planktonic cells) has caused any decrease in the metabolic activity of the staphylococcal cells forming the biofilm. The kinetic time–kill assay revealed some important differences in the activity of these substances. Compound 33 is bacteriostatic, while the other three demonstrate bactericidal activity.

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1,2,3-Triazine Scaffold as a Potent Biologically Active Moiety: A Mini Review

Cited by 41 publications

References 0 publications

Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

Hybrid molecules based on 1,3,5‐triazine as potential therapeutics: A focused review

Anthra[1,2-d][1,2,3]triazine-4,7,12(3H)-triones as a New Class of Antistaphylococcal Agents: Synthesis and Biological Evaluation

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