Recent Advances in 1,3,5-Triazine Derivatives as Antibacterial Agents

2020 ◽  
Vol 17 (8) ◽  
pp. 991-1041
Author(s):  
Divya Utreja ◽  
Jagdish Kaur ◽  
Komalpreet Kaur ◽  
Palak Jain
Keyword(s):  
Antibacterial Activity ◽  
Heterocyclic Compounds ◽  
Antibacterial Agents ◽  
Rapid Development ◽  
Pharmacological Action ◽  
Biological Properties ◽  
Vast Array ◽  
Bacterial Diseases ◽  
New Class ◽  
Triazine Derivatives

Triazine, one of the nitrogen containing heterocyclic compounds has attracted the considerable interest of researchers due to the vast array of biological properties such as anti-viral, antitumor, anti-convulsant, analgesic, antioxidant, anti-depressant, herbicidal, insecticidal, fungicidal, antibacterial and anti-inflammatory activities offered by it. Various antibacterial agents have been synthesized by researchers to curb bacterial diseases but due to rapid development in drug resistance, tolerance and side effects, there had always been a need for the synthesis of a new class of antibacterial agents that would exhibit improved pharmacological action. Therefore, this review mainly focuses on the various methods for the synthesis of triazine derivatives and their antibacterial activity.

Large-scale High-throughput Screening Revealed 5'-(carbonylamino)-2,3'- bithiophene-4'-carboxylate as Novel Template for Antibacterial Agents

2020 ◽  
Vol 17 (5) ◽  
pp. 716-724
Author(s):  
Yan A. Ivanenkov ◽  
Renat S. Yamidanov ◽  
Ilya A. Osterman ◽  
Petr V. Sergiev ◽  
Vladimir A. Aladinskiy ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
High Throughput ◽  
High Throughput Screening ◽  
Large Scale ◽  
Antibacterial Agents ◽  
Sos Response ◽  
Luciferase Assay ◽  
Translational Machinery ◽  
E Coli ◽  
New Class

Background: The key issue in the development of novel antimicrobials is a rapid expansion of new bacterial strains resistant to current antibiotics. Indeed, World Health Organization has reported that bacteria commonly causing infections in hospitals and in the community, e.g. E. Coli, K. pneumoniae and S. aureus, have high resistance vs the last generations of cephalosporins, carbapenems and fluoroquinolones. During the past decades, only few successful efforts to develop and launch new antibacterial medications have been performed. This study aims to identify new class of antibacterial agents using novel high-throughput screening technique. Methods: We have designed library containing 125K compounds not similar in structure (Tanimoto coeff.< 0.7) to that published previously as antibiotics. The HTS platform based on double reporter system pDualrep2 was used to distinguish between molecules able to block translational machinery or induce SOS-response in a model E. coli system. MICs for most active chemicals in LB and M9 medium were determined using broth microdilution assay. Results: In an attempt to discover novel classes of antibacterials, we performed HTS of a large-scale small molecule library using our unique screening platform. This approach permitted us to quickly and robustly evaluate a lot of compounds as well as to determine the mechanism of action in the case of compounds being either translational machinery inhibitors or DNA-damaging agents/replication blockers. HTS has resulted in several new structural classes of molecules exhibiting an attractive antibacterial activity. Herein, we report as promising antibacterials. Two most active compounds from this series showed MIC value of 1.2 (5) and 1.8 μg/mL (6) and good selectivity index. Compound 6 caused RFP induction and low SOS response. In vitro luciferase assay has revealed that it is able to slightly inhibit protein biosynthesis. Compound 5 was tested on several archival strains and exhibited slight activity against gram-negative bacteria and outstanding activity against S. aureus. The key structural requirements for antibacterial potency were also explored. We found, that the unsubstituted carboxylic group is crucial for antibacterial activity as well as the presence of bulky hydrophobic substituents at phenyl fragment. Conclusion: The obtained results provide a solid background for further characterization of the 5'- (carbonylamino)-2,3'-bithiophene-4'-carboxylate derivatives discussed herein as new class of antibacterials and their optimization campaign.

scholarly journals 1,4-Naphthoquinone Analogues: Potent Antibacterial Agents and Mode of Action Evaluation

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1437 ◽  
Author(s):  
Palanisamy Ravichandiran ◽  
Sunirmal Sheet ◽  
Dhanraj Premnath ◽  
Ae Rhan Kim ◽  
Dong Jin Yoo
Keyword(s):  
Antibacterial Activity ◽  
Mode Of Action ◽  
Bacterial Infections ◽  
Antibacterial Agents ◽  
Annexin V ◽  
Ros Generation ◽  
Redox Potentials ◽  
Bacterial Strains ◽  
E Coli ◽  
New Class

1,4-Naphthoquinones have antibacterial activity and are a promising new class of compound that can be used to treat bacterial infections. The goal was to improve effective antibacterial agents; therefore, we synthesized a new class of naphthoquinone hybrids, which contain phenylamino-phenylthio moieties as significant counterparts. Compound 4 was modified as a substituted aryl amide moiety, which enhanced the antibacterial activity of earlier compounds 3 and 4. In this study, five bacterial strains Staphylococcus aureus (S. aureus), Listeria monocytogenes (L. monocytogenes), Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa) and Klebsiella pneumoniae (K. pneumoniae) were used to evaluate the antibacterial potency of synthesized naphthoquinones using the minimal inhibitory concentration (MIC) method. Most of the studied naphthoquinones demonstrated major antibacterial activity with a MIC of 15.6 µg/mL–500 µg/mL. Selected compounds (5a, 5f and 5x) were studied for the mode of action, using intracellular ROS generation, determination of apoptosis by the Annexin V-FITC/PI assay, a bactericidal kinetic study and in silico molecular modelling. Additionally, the redox potentials of the specified compounds were confirmed by cyclic voltammetry (CV).

scholarly journals A Novel Synthesis, Characterization and Biological Studies of Ferrocenyl Substituted Pyrazoles

2019 ◽  
Vol 31 (12) ◽  
pp. 2729-2732
Author(s):  
Manoj Kumar ◽  
Shashi Sharma ◽  
Hardeep Singh Tuli ◽  
Rajshree Khare
Keyword(s):  
Heterocyclic Compounds ◽  
Biological Properties ◽  
Spectroscopic Techniques ◽  
Single Product ◽  
Phenyl Hydrazine ◽  
Natural Activity ◽  
New Class ◽  
Novel Synthesis ◽  
Biological Studies ◽  
Substituted Pyrazoles

It has been discovered that ferrocenyl substituted heterocyclic compounds have wide scope of restorative methodology. The combination of ferrocenyl substituted pyrazole is the new class in these compounds with upgraded natural activity. This work center around blend of ferrocenyl substituted pyrazoles through novel course. The combination of 1-phenyl-3-ferrocenyl-pyrazole was examined including addition-cyclocondensation like response conditions. The response continued through three phases using of expansion cyclo-buildup of acetyl ferrocene with phenyl hydrazine pursued by cyclizing reagent iodine with NaHCO3. In both syntheses, each time single product isolated having good yields (87 and 79 %). Ferrocenyl substituted pyrazoles were examined by spectroscopic techniques (1H NMR, IR, MS) and their biological properties have been screened.

scholarly journals Synthesis of Phenyl-1,3-thiazole Substituted Amino s-triazines as Antibacterial Agents

1970 ◽  
Vol 7 (2) ◽  
pp. 107-111 ◽  
Author(s):  
Prashant Gahtori ◽  
BK Singh ◽  
Aparoop Das
Keyword(s):  
Antibacterial Activity ◽  
Physicochemical Properties ◽  
Antibacterial Agents ◽  
Bacterial Resistance ◽  
Salmonella Typhi ◽  
Dilution Technique ◽  
Triazine Derivatives ◽  
In Vitro Antibacterial Activity ◽  
Broth Dilution

Amino s-triazines are widely believed to exert their antibacterial effects by nonspecific mechanisms. We assessed the extent to which physicochemical properties can be exploited to promote discriminative activity. In a wide search program towards new and efficient antibacterial agents, a series of amino substituted s-triazines were synthesized and subsequently screened for their in-vitro antibacterial activity against three Gram positive (Bacillus subtilis, B. cereus, Staphylococcus aureus) and three Gram-negative microorganism (Salmonella typhi, Escherichia coli, Klebsiella aerogenes) by the broth dilution technique, recommended by European Committee for antimicrobial susceptibility testing (EUCAST) with reference to streptomycin. The phenyl-1,3-thiazole substituted amino-s-triazine derivatives showed good antibacterial activity. Key words: Antibacterial activity, Bacterial resistance, Broth dilution technique, Physicochemical properties, s-Triazine. doi: 10.3329/dujps.v7i2.2164 Dhaka Univ. J. Pharm. Sci. 7(2): 107-111, 2008 (December)

3-Aminoquinazolinediones as a New Class of Antibacterial Agents Demonstrating Excellent Antibacterial Activity Against Wild-Type and Multidrug Resistant Organisms

2006 ◽  
Vol 49 (22) ◽  
pp. 6435-6438 ◽  
Author(s):  
Edmund L. Ellsworth ◽  
Tuan P. Tran ◽  
H. D. Hollis Showalter ◽  
Joseph P. Sanchez ◽  
Brian M. Watson ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Antibacterial Agents ◽  
Multidrug Resistant ◽  
Wild Type ◽  
New Class ◽  
Multidrug Resistant Organisms

scholarly journals Design, synthesis and antibacterial activity of new phthalazinedione derivatives

2011 ◽  
Vol 76 (3) ◽  
pp. 329-339 ◽  
Author(s):  
El-Galil Khalil ◽  
Moged Berghot ◽  
Mostafa Gouda
Keyword(s):  
Antibacterial Activity ◽  
Sodium Hydroxide ◽  
Ring Opening ◽  
Antibacterial Agents ◽  
Acetyl Chloride ◽  
Triazole Derivative ◽  
Design Synthesis ◽  
Gewald Reaction ◽  
Triazine Derivatives ◽  
Thiophene Derivatives

Dibenzobarrelene (1) was utilized as the key intermediate for the synthesis of some new 2-substituted (1,4-dioxo-3,4,4e,5,10,10ahexahydro- 1H-5,10-benzeno-benzo[g]phthalazine: 2, 5a-d, 8a-c and 10. Condensation of 2 with benzaldehyde or anisaldehyde gave the corresponding acrylonitrile derivative 3a, b, respectively. Thiophene derivatives 4a, b were obtained via the Gewald reaction of 2 with cyclohexanone or pentanone, respectively. Treatment of 5d with acetyl chloride or p-toluenesulfonyl chloride afforded the corresponding esters 6, 7, respectively. Cyclization of 8a-c with formalin afforded the corresponding triazine derivatives 9a-c. Ring opening of 10 with sodium hydroxide gave the corresponding triazole derivative 11, which when alkylated with pentyl bromide afforded the pentylsulfanyl derivative 12. Representative compounds of the synthesized products were established and evaluated as antibacterial agents.

Design, synthesis, antibacterial activity evaluation and molecular modeling studies of new sulfonamides containing sulfathiazole moiety

2021 ◽  
Author(s):  
Tuğba Meşeli ◽  
Şengül Dilem Doğan ◽  
Miyase Gözde Gündüz ◽  
Zulbiye Onal ◽  
Sanja Skaro Bogojevic ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Molecular Modeling ◽  
Antibacterial Agents ◽  
Central Position ◽  
Design Synthesis ◽  
Bacterial Diseases ◽  
Activity Evaluation ◽  
Modeling Studies ◽  
Molecular Modeling Studies

Sulfonamides represent the oldest synthetic antibacterial agents; however, their central position in controlling bacterial diseases has been seriously damaged by the development of widespread resistance. Hereby, we revisited sulfathiazole, a...

scholarly journals Synthesis, Antibacterial, and Antioxidant Evaluation of Novel Series of Condensed Thiazoloquinazoline with Pyrido, Pyrano, and Benzol Moieties as Five- and Six-Membered Heterocycle Derivatives

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 357
Author(s):  
Ebraheem Abdu Musad Saleh ◽  
Abdullah Mohammed AL Dawsari ◽  
Kakul Husain ◽  
Ismail Hassan Kutty ◽  
K.M.Lokanatha Rai
Keyword(s):  
Antibacterial Activity ◽  
Heterocyclic Compounds ◽  
Antibacterial Agents ◽  
Biological Evaluation ◽  
Bacterial Strains ◽  
E Coli ◽  
Antioxidant Evaluation ◽  
Synthetic Approaches ◽  
Membered Heterocycle ◽  
Molecular Framework

A novel synthesis of thiazolo[2,3-b]quinazolines 4(a–e), pyrido[2′,3′:4,5]thiazolo[2,3-b]quinazolines {5(a–e), 6(a–e), and 7(a–e)}, pyrano[2′,3′:4,5]thiazolo[2,3-b]quinazolines 8(a–e), and benzo[4,5]thiazolo[2,3-b]quinazoloine9(a–e) derivatives starting from 2-(Bis-methylsulfanyl-methylene)-5,5-dimethyl-cyclohexane-1,3-dione 2 as efficient α,α dioxoketen dithioacetal is reported and the synthetic approaches of these types of compounds will provide an innovative molecular framework to the designing of new active heterocyclic compounds. In our study, we also present optimization of the synthetic method along with a biological evaluation of these newly synthesized compounds as antioxidants and antibacterial agents against the bacterial strains, like S. aureus, E. coli, and P. aeruginosa. Among all the evaluated compounds, it was found that some showed significant antioxidant activity at 10 μg/mL while the others exhibited better antibacterial activity at 100 μg/mL. The results of this study showed that compound 6(c) possessed remarkable antibacterial activity, whereas compound 9(c) exhibited the highest efficacy as an antioxidant. The structures of the new synthetic compounds were elucidated by elemental analysis, IR, 1H-NMR, and 13C-NMR.

Anodyne activities of New Tetrazole derivatives from Triazine

2020 ◽  
Vol 11 (3) ◽  
pp. 3377-3383
Author(s):  
Arulmozhi R ◽  
Abirami N ◽  
Helen P Kavitha ◽  
Arulmurugan S ◽  
Vinoth Kumar J
Keyword(s):  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Pharmaceutical Chemistry ◽  
Tail Flick ◽  
Structural Fragment ◽  
Hot Plate ◽  
Standard Drug ◽  
New Class ◽  
Novel Drugs ◽  
Tetrazole Derivatives

The creation of novel drugs containing a tetrazole ring as a structural fragment has contributed considerably to the outstanding achievements of the pharmaceutical chemistry in the last decade. Tetrazoles are the heterocyclic compounds having diverse biological activities such as analgesic, antiinflammation, antimicrobial, anticancer, antidiabetic, etc., and an impending source in biosciences. In this paper, the authors describe the synthesis of novel tetrazoles from N, N-( 6-Phenyl-1,3,5-triazine-2,4-diyl) dibenzamide (PTDDB) and 2-phenyl-4, 6-di(2H-tetrazole-2-yl)-1,3,5-triazine(5a-i) were prepared per the proposed scheme. A new class of tetrazole heterocycles were synthesised and characterised. I n vivo analysis was carried out on the analgesic property of synthesised tetrazole derivatives (5a, 5b, 5c). Characterisation studies such as IR, 1H NMR, 13C NMR, Mass and elemental analysis were performed for the synthesised tetrazole derivatives. Some of the tetrazole derivatives 5a, 5b, and 5c were tested for anodyne activity using morphine as the standard drug. The data reveals that all the three compounds 5a, 5b and 5c taken for the study show analgesic activity by hot plate method and tail flick methods. Among tested compounds, compound 5c is found to have potent analgesic (anodyne) activity. The results of the study indicate that the sample taken for the study show fairly good business using morphine as the standard drug.

Diverse chemical and biological potentials of various pyridazine and pyridazinone derivatives

2019 ◽  
Author(s):  
Chem Int
Keyword(s):  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Wide Spectrum ◽  
Biological Properties ◽  
Industrial Chemical ◽  
Anti Inflammatory ◽  
Pyridazinone Derivatives

A series of heterocyclic compounds incorporating pyridazine moiety were for diverse biological activities. Pyridazines and pyridazinones derivatives showed wide spectrum of biological activities such as vasodialator, cardiotonic, anticonvulsant, antihypertensive, antimicrobial, anti-inflammatory, analgesic, anti-feedant, herbicidal, and various other biological, agrochemical and industrial chemical activities. The results illustrated that the synthesized pyridazine/pyridazine compounds have diverse and significant biological activities. Mechanistic insights into the biological properties of pyridazinone derivatives and various synthetic techniques used for their synthesis are also described.

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