Thiazole-based aminopyrimidines and N-phenylpyrazolines as potent antimicrobial agents: synthesis and biological evaluation

Λιάρας, Κωνσταντίνος; Geronikaki, Athina; Glamočlija, Jasmina; Ćirić, Ana; Sokóvić, Marina

doi:10.1039/c4md00124a

Cited by 16 publications

(7 citation statements)

References 30 publications

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“…In particular, thiazole is a well-known heterocyclic aromatic compound that contains sulfur and nitrogen atoms at positions 1 and 3 of its five-member ring, respectively [ 20 ]. Τhiazole moiety can be found in numerous biologically active compounds of natural origin (e.g., thiamine [ 19 , 20 ], mycothiazole [ 21 ], cystothiazole C [ 22 ], as well as synthetic molecules possessing a wide range of pharmacological activities such as antimicrobial [ 23 , 24 , 25 , 26 , 27 , 28 ], antiviral [ 29 , 30 ], antitubercular [ 23 , 31 ], anti-inflammatory [ 32 , 33 , 34 ], anxiolytic [ 35 ], anaesthetic [ 36 ], anticonvulsant [ 37 , 38 , 39 , 40 ], etc.). There is a large number of known marketed drugs containing thiazole rings, such as the anthelmintic tiabendazole, the antibacterial sulfathiazole, the anticonvulsant riluzole, the anti-ulcer alizatidine, the antiparkinsonian talipexole, the antischistosomal niridazole, the antiviral ritonavir and the anti-inflammatory meloxicam.…”

Section: Introductionmentioning

confidence: 99%

Thiazoles and Thiazolidinones as COX/LOX Inhibitors

2018

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Inflammation is a natural process that is connected to various conditions and disorders such as arthritis, psoriasis, cancer, infections, asthma, etc. Based on the fact that cyclooxygenase isoenzymes (COX-1, COX-2) are responsible for the production of prostaglandins that play an important role in inflammation, traditional treatment approaches include administration of non-steroidal anti-inflammatory drugs (NSAIDs), which act as selective or non-selective COX inhibitors. Almost all of them present a number of unwanted, often serious, side effects as a consequence of interference with the arachidonic acid cascade. In search for new drugs to avoid side effects, while maintaining high potency over inflammation, scientists turned their interest to the synthesis of dual COX/LOX inhibitors, which could provide numerous therapeutic advantages in terms of anti-inflammatory activity, improved gastric protection and safer cardiovascular profile compared to conventional NSAIDs. Τhiazole and thiazolidinone moieties can be found in numerous biologically active compounds of natural origin, as well as synthetic molecules that possess a wide range of pharmacological activities. This review focuses on the biological activity of several thiazole and thiazolidinone derivatives as COX-1/COX-2 and LOX inhibitors.

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Section: Introductionmentioning

confidence: 99%

Thiazoles and Thiazolidinones as COX/LOX Inhibitors

2018

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“…Despite the availability of a large number of antibiotics and chemotherapeutics, the increasing clinical importance of drug-resistant microbial pathogens have lent additional urgency in microbiological and antifungal research [1e4]. They display quite a broad spectrum of biological activities [6], which have found applications in the treatment of allergies [7], hypertension [8], inflammation [9], schizophrenia [10], microbial infections [11,12], HIV infections [13], hypnotics [14] and pain [15]. In this context, thiazole derivatives have been playing a crucial role in medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles

Desai

Bhatt

Somani

et al. 2013

European Journal of Medicinal Chemistry

141

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A series of thiazole clubbed 1,3,4-oxadiazole derivatives (5a-l) have been synthesized and characterized by IR, (1)H NMR, (13)C NMR and mass spectral analysis. Synthesized compounds were evaluated for their antimicrobial and cytotoxic activities. The results indicated that, compounds 5c and 5i exhibited the most potent antibacterial activity. Compound 5f was found to be the most potent antifungal agent. The structure activity relationship revealed that the presence of electron withdrawing groups at para position of phenyl ring remarkably enhanced the antibacterial activity of synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 5b, 5c, 5f, 5h and 5i is accompanied by low cytotoxicity.

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“…Compound 38 inhibited the growth of all pathogens tested (MIC 31.25 µg/mL for Gram-positive bacteria), which might be due to the presence of a 3-carbamoyl-4-hydroxy-phenyl group [83]. Liaras et al (2014) produced and tested a variety of amino-pyrimidine derivatives based on thiazoles for antibacterial activity. The synthesis of aimed N-phenylpyrazolines and amino-pyrimidines was afforded by heterocyclization of the corresponding chalcones with phenylhydrazine hydrochloride and guanidine hydrochloride in the presence of sodium hydroxide.…”

Section: Thiazoles As Antimicrobial Agentsmentioning

confidence: 99%

“…Molecules 39a and 39b showed a better activity profile when compared to the reference drugs ampicillin and streptomycin. The SAR analysis revealed that the presence of NHCH 3 and a phenyl group on the side chain are essential for the activity [84]. Some novel thiazole compounds have been identified as promising antibacterial agents in a recent investigation.…”

Section: Thiazoles As Antimicrobial Agentsmentioning

confidence: 99%

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Arshad¹,

Alam

Alshammari

et al. 2022

Molecules

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For many decades, the thiazole moiety has been an important heterocycle in the world of chemistry. The thiazole ring consists of sulfur and nitrogen in such a fashion that the pi (π) electrons are free to move from one bond to other bonds rendering aromatic ring properties. On account of its aromaticity, the ring has many reactive positions where donor–acceptor, nucleophilic, oxidation reactions, etc., may take place. Molecules containing a thiazole ring, when entering physiological systems, behave unpredictably and reset the system differently. These molecules may activate/stop the biochemical pathways and enzymes or stimulate/block the receptors in the biological systems. Therefore, medicinal chemists have been focusing their efforts on thiazole-bearing compounds in order to develop novel therapeutic agents for a variety of pathological conditions. This review attempts to inform the readers on three major classes of thiazole-bearing molecules: Thiazoles as treatment drugs, thiazoles in clinical trials, and thiazoles in preclinical and developmental stages. A compilation of preclinical and developmental thiazole-bearing molecules is presented, focusing on their brief synthetic description and preclinical studies relating to structure-based activity analysis. The authors expect that the current review may succeed in drawing the attention of medicinal chemists to finding new leads, which may later be translated into new drugs.

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Thiazole-based aminopyrimidines and N-phenylpyrazolines as potent antimicrobial agents: synthesis and biological evaluation

Abstract: A series of eight thiazole-based N-phenylpyrazolines and two aminopyrimidines having several chalcone derivatives as precursors have been synthesized and evaluated for their antimicrobial activity.

Cited by 16 publications

References 30 publications

Thiazoles and Thiazolidinones as COX/LOX Inhibitors

Thiazoles and Thiazolidinones as COX/LOX Inhibitors

Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

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