Synthesis, identification and antimicrobial activity of substituted thiazolines and 1,3,4-thiadiazines from dehydroacetic acid

Nechak, Rosa; Bouzroura, Samia Achouche; Benmalek, Yamina; Boufroua, Naouel; Kolli, Bellara; Martini, Sophie; Duñach, Élisabet

doi:10.1080/00397911.2019.1606918

Cited by 11 publications

(5 citation statements)

References 32 publications

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“…antimicrobial [31][32][33], antidiabetic [34][35][36], antitubercular, [37][38], antiviral [39][40] and anticancer activities [41][42][43]. For example, [N-(4-acetyl-4,5-dihydro-5-methyl-5-phenyl-1,3,4thiadiazol-2-yl)acetamide] (D in Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and evaluation of anticancer activities of some novel heterocyclic compounds based on thymol

Laamari

Bimoussa

Fawzi

et al. 2023

Journal of Molecular Structure

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Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and evaluation of anticancer activities of some novel heterocyclic compounds based on thymol

Laamari

Bimoussa

Fawzi

et al. 2023

Journal of Molecular Structure

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“…In addition, other thiadiazines have been studied to evaluate their antibacterial activity, including synthetic and plant-derived compounds. These studies showed that thiadiazines have the potential to be used as promising antibacterial agents [10].…”

Section: Discussionmentioning

confidence: 99%

“…Therefore, research and development of new substances and drugs against MDR strains have been prioritized by the World Health Organization (WHO) [8]. In this context, thiadiazines are substances that may play an important role in this scenario, since their antibacterial activity has already been proven against some bacterial strains [9,10].…”

Section: Introductionmentioning

confidence: 99%

“…Thiadiazines are heterocyclic compounds that contain two nitrogen atoms and one sulfur atom in their structure [11]. These synthetic molecules have several relevant pharmacological activities, such as antifungal [12], antibacterial [10], and antiparasitic [13]. However, the modifying activity of antibiotics against MDR strains by substances from the thiadiazine group remains unknown.…”

Section: Introductionmentioning

confidence: 99%

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Potentiating‐antibiotic activity and absorption, distribution, metabolism, excretion and toxicity properties (ADMET) analysis of synthetic thiadiazines against multi‐drug resistant (MDR) strains

de Araújo,

Freitas,

Araújo

et al. 2023

Fundamemntal Clinical Pharma

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BackgroundThiadiazines are heterocyclic compounds that contain two nitrogen atoms and one sulfur atom in their structure. These synthetic molecules have several relevant pharmacological activities, such as antifungal, antibacterial, and antiparasitic.ObjectivesThe present study aimed to evaluate the possible in vitro and in silico interactions of compounds derived from thiadiazines.MethodsThe compounds were initially synthesized, purified, and confirmed through HPLC methodology. Multi‐drug resistant bacterial strains of Staphylococcus aureus 10 and Pseudomonas aeruginosa 24 were used to evaluate the direct and modifying antibiotic activity of thiadiazine derivatives. ADMET assays (absorption, distribution, metabolism, excretion, and toxicity) were conducted, which evaluated the influence of the compounds against thousands of macromolecules considered as bioactive targets.ResultsThere were modifications in the chemical synthesis in carbon 4 or 3 in one of the aromatic rings of the structure where different ions were added, ensuring a variability of products. It was possible to observe results that indicate the possibility of these compounds acting through the cyclooxygenase 2 mechanism, which, in addition to being involved in inflammatory responses, also acts by helping sodium reabsorption. The amine group present in thiadiazine analogs confers hydrophilic characteristics to the substances, but this primary characteristic has been altered due to alterations and insertions of other ligands. The characteristics of the analogs generally allow easy intestinal absorption, reduce possible hepatic toxic effects, and enable possible neurological and anti‐inflammatory action. The antibacterial activity tests showed a slight direct action, mainly of the IJ23 analog. Some compounds were able to modify the action of the antibiotics gentamicin and norfloxacin against multi‐drug resistant strains, indicating a possible synergistic action.ConclusionsAmong all the results obtained in the study, the relevance of thiadiazine analogs as possible coadjuvant drugs in the antibacterial, anti‐inflammatory, and neurological action with low toxicity is clear. Need for further studies to verify these effects in living organisms is not ruled out.

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“…Nechak et al synthesized some thiazolines and 1,3,4‐thiadiazines based on a DHA scaffold and screened their antimicrobial potential toward various microbial strains. [ 47 ] Among the synthesized compounds, 11 and 12 possessed the highest activity with ZOI of 24 mm and 20 mm, respectively against Micrococcus luteus , whereas 11 and 13 demonstrated more significant activity with ZOI of 20 and 19 mm, respectively against C. albicans . The SAR studies demonstrated that compounds possessing ethyl or phenyl radicals on thiazoline or 1,3,4‐thiadiazine rings exhibited better activity.…”

Section: Biological Activities Of Dha‐based Compoundsmentioning

confidence: 99%

Dehydroacetic acid a privileged medicinal scaffold: A concise review

Grover,

Kumar,

Tittal

et al. 2023

Archiv der Pharmazie

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From the last decade, research on dehydroacetic acid (DHA) and its derivatives has increased immensely due to its significant role in various fields, including medicine, cosmetics, food industry, and so on. In the medicinal area, DHA plays an essential role in developing novel action‐based drugs, which are helpful for treating various diseases. Besides its plethora of biological applications, its chelating ability offers the easiest synthetic route for synthesizing more active metal complexes. DHA derivatives along with their metal complexes show a number of biological activities and also exhibit various interactions with multiple biological targets. This article summarizes recent medicinal applications (2000‐onwards) of DHA‐based compounds and their analogs, along with their structure–activity relationship (SAR) analysis. Their interactions with different target enzymes are also discussed. This information derived from SAR analysis would be helpful for medicinal chemists working on the development of drugs based on heterocyclic frameworks, particularly those based on the DHA scaffold.

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Synthesis, identification and antimicrobial activity of substituted thiazolines and 1,3,4-thiadiazines from dehydroacetic acid

Cited by 11 publications

References 32 publications

Synthesis, crystal structure and evaluation of anticancer activities of some novel heterocyclic compounds based on thymol

Synthesis, crystal structure and evaluation of anticancer activities of some novel heterocyclic compounds based on thymol

Potentiating‐antibiotic activity and absorption, distribution, metabolism, excretion and toxicity properties (ADMET) analysis of synthetic thiadiazines against multi‐drug resistant (MDR) strains

Dehydroacetic acid a privileged medicinal scaffold: A concise review

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