Design, Facile Synthesis, Antibacterial Activity and Structure-Activity Relationship of Novel Di- and Tri-Substituted 1,3,5-Triazines

Ghosh, Surajit Kumar; Saha, Ashmita; Hazarika, Bornali; Singh, Udaya Pratap; Bhat, Hans Raj; Gahtori, Prashant

doi:10.2174/157018012799129846

Cited by 19 publications

(6 citation statements)

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“…Owing to a wide range of biological applications, s-triazine nucleus has received an immense attention among chemists through fertile source of pharmacological activities such as antibacterial (Bhushan Singh et al, 2012;Gahtori et al, 2012b;Kumar Ghosh et al, 2012), antimalarial (Gahtori et al, 2012a), antiprotozoal (Baliani et al, 2005), antifungal (Singh et al, 2012), anticancer (Menicagli et al, 2004), antimycobacterial (Patel et al, 2012), and antiviral (Chen et al, 2012). In addition to this several s-triazine derivatives bearing p-amino benzonitrile moiety have been found to possess an enhanced antimicrobial profile and improved antitubercular (Patel et al, 2011b) and profound anticancer activity (Patel et al, 2011a) as well.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel s-triazine based aryl/heteroaryl entities: Design, rationale and comparative study

Mewada

Shah

Lakum

et al. 2016

Journal of the Association of Arab Universities for Basic and A

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The urgent need in search of new biological entities to fight back with recent drugresistant microbial flora, has led us report a library of s-triazine derivatives. The intermediate 4-((4-chloro-6-methoxy-1,3,5-triazin-2-yl)amino)benzonitrile 3 was substituted with various thiophenol, phenol, aniline and piperazine/piperidine/morpholine moieties to furnish the final 35 target compounds i.e. (4a-j), (5a-j), (6a-g) and (7a-h), respectively. These compounds were screened for in vitro antibacterial evaluation against bacteria (Staphylococcus aureus MTCC 96, Bacillus cereus MTCC 619, Escherichia coli MTCC 739, and Pseudomonas aeruginosa MTCC 741) and antifungal activity against fungi (Candida albicans MTCC 183, Aspergillus niger MTCC 282, and Aspergillus clavatus MTCC 1323). The title compounds were further subjected for antituberculosis activity against Mycobacterium tuberculosis H37Rv strain using the BACTEC MGIT method. In this biological evaluation, thiophenol derivatives were found to be more active than the rest (i.e. -Thiophenol > -piperazine > -Aniline > -phenol). The final compounds were characterized by FT-IR, 1 H NMR, 13 C NMR, mass spectroscopy and elemental analysis.

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Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel s-triazine based aryl/heteroaryl entities: Design, rationale and comparative study

Mewada

Shah

Lakum

et al. 2016

Journal of the Association of Arab Universities for Basic and A

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“…1,3,5-Triazine is most privileged and explored much to have extensive antimicrobial profile. [61,62] Patil et al [63] described the synthesis of 1, 3, 5-triazine derivatives as antimicrobial agents. The desired compounds were prepared by a single-step reaction of 2-cyanoguanidine with benzonitrile and its derivatives, in the presence of ethyl ethanol and potassium hydroxide combination.…”

Section: Antimicrobial (Antibacterial/antifungal) Activitymentioning

confidence: 99%

“…The nitrogen‐containing six‐membered scaffolds such as triazines have attracted the attention of chemists and can exist as different isomers including 1,2,3‐triazine, 1,2,4‐triazine, and 1,3,5‐triazines. 1,3,5‐Triazine is most privileged and explored much to have extensive antimicrobial profile [61,62] …”

Section: Biological Activities Of 135‐triazine and Its Analoguesmentioning

confidence: 99%

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

Rathod,

Pawar,

Puri

et al. 2024

ChemistrySelect

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Nitrogen‐bearing heterocycles are ubiquitous in landscapes and have a great impact on living nature. Structural motifs are present in diverse natural products like vitamins, antibiotics, and alkaloids, as well as pharmaceuticals. The 1,3,5‐Triazines are the primitive class of heterocyclic motifs and are used in various synthetic and medicinal applications. This review covers an exhaustive exploration of literature reports and describes various synthetic strategies and pharmacological activities of 1,3,5‐triazine moiety. Synthetic strategies include multicomponent reaction, metal catalyst reaction, microwave‐assisted strategy, etc. to construct 1,3,5‐triazine moiety. Pharmacological activities include anticancer, antimalarial, antibacterial, antifungal, antiviral, anti‐tubercular, anti‐leishmanial, anti‐inflammatory, histamine antagonist, serotonin antagonist, etc. For anticancer activity, 1,3,5‐triazine moiety‐containing compounds were tested on different cell lines, and inhibitory activity was also mentioned. The involvement of this scaffold in the treatment of various diseases and disorders makes this scaffold important from a research perspective. Therefore, there is a need to present the combined data of research and reviews to the researchers to develop new molecules. For that reason, the review included information from articles published from 1978 onwards.

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“…It is used to predict the preferred orientation, affinity and activity of ligands (small molecules) into the active site of target protein through a process involving series of steps. In continuation of our research endeavour on discovery of novel anti-infective agents from 1,3,5-triazines (Gahtori et al 2009; Singh et al 2011; Bhat et al 2011; Gahtori et al 2012a; Gahtori et al 2012b; Gahtori and Ghosh et al 2012; Ghosh et al 2012; Bhat et al 2012, Singh et al 2012). We have tried to work out the inhibitory effect of hybrid phenylthiazole-1,3,5-triazines on the candida albicans cytosolic leucyl-tRNA synthetase editing domain through molecular docking studies to elucidate probable mechanism of action of 1,3,5-triazine as antifungal agent.…”

Section: Introductionmentioning

confidence: 99%

Hybrid phenylthiazole and 1,3,5-triazine target cytosolic leucyl-tRNA synthetase for antifungal action as revealed by molecular docking studies

Singh

Bhat

Gahtori

et al. 2013

In Silico Pharmacol.

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BackgroundLeucyl-tRNA synthetase (LeuRS) is one of the essential enzymes belonging to the family of aminoacyl-tRNA synthetases (aaRSs), which executes the translation of genetic code by catalyzing the specific attachment of amino acids to their cognate tRNAs. This process is very crucial for survival of micro-organism and thus the inhibition of LeuRS offered a novel and lucrative target for developing new antimicrobials.FindingsDocking studies using hybrid phenylthiazole-1,3,5-triazine derivatives revealed that these molecules acted as probable inhibitors of candida albicans cytosolic leucyl-tRNA synthetaseConclusionThe conjugates of phenylthiazole and 1,3,5-triazine can act as lead molecules towards the development of potential leucyl-tRNA synthetase inhibitors on the basis of molecular docking runs, which contribute to the possible mechanism of antifungal activity of these analogues.

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Design, Facile Synthesis, Antibacterial Activity and Structure-Activity Relationship of Novel Di- and Tri-Substituted 1,3,5-Triazines

Cited by 19 publications

References 0 publications

Synthesis and biological evaluation of novel s-triazine based aryl/heteroaryl entities: Design, rationale and comparative study

Synthesis and biological evaluation of novel s-triazine based aryl/heteroaryl entities: Design, rationale and comparative study

Recent Advancements and Developments in the Biological Importance of 1,3,5‐Triazines

Hybrid phenylthiazole and 1,3,5-triazine target cytosolic leucyl-tRNA synthetase for antifungal action as revealed by molecular docking studies

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