Synthesis and Biological Activities of Ethyl 2-(2-pyridylacetate) Derivatives Containing Thiourea, 1,2,4-triazole, Thiadiazole and Oxadiazole Moieties

Szulczyk, Daniel; Tomaszewski, Piotr; Jóźwiak, Michał; Kozioł, Anna E.; Lis, Tadeusz; Collu, David; Iuliano, Filippo; Struga, Marta

doi:10.3390/molecules22030409

Cited by 19 publications

(14 citation statements)

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“…The series of 5-(pyridin-2-ylmethyl)-1,3,4-thiadiazol-2-amine derivatives 11-16 were synthesized by intramolecular cyclization of the corresponding hydrazinecarbothioamides under acidic conditions and the activity against HIV-1 was tested on MT-4 cells by MTT assay using efavirenz as a standard drug [64]. Molecular modeling studies for the pyrimidyl derivative 10 showed the formation of two potential intermolecular hydrogen bonds involving a nitrogen atom and the amino group of the thiadiazole ring and aminoacids from NNBS of RT.…”

Section: -10mentioning

confidence: 99%

Section: -10mentioning

confidence: 99%

“…The conversion of glutamine to glutamate is catalyzed by the mitochondrial enzyme, glutaminase [72,75]. Subsequent chemical modifications by substitutions on aromatic rings with different groups may lead to compounds with improved activity [64]. Thus, glutamine and glutamate are Except for derivative 11 which showed low activity (EC 50 values of 47 µM), the activity of the other compounds was even lower (EC 50 values > 70 µM) proving that substitution with halogens or halogenoalkyl groups at C3 and/or C4 of phenyl ring led to a decrease or loss of activity ( Figure 3).…”

Section: -16mentioning

confidence: 99%

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Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

Şerban

2020

Molecules

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Viral infections have resulted in millions of victims in human history. Although great efforts have been made to find effective medication, there are still no drugs that truly cure viral infections. There are currently approximately 90 drugs approved for the treatment of human viral infections. As resistance toward available antiviral drugs has become a global threat to health, there is an intrinsic need to identify new scaffolds that are useful in discovering innovative, less toxic and highly active antiviral agents. 1,3,4-Thiadiazole derivatives have been extensively studied due to their pharmacological profile, physicochemical and pharmacokinetic properties. This review provides an overview of the various synthetic compounds containing the 2-amino-1,3,4-thiadiazole moiety that has been evaluated for antiviral activity against several viral strains and could be considered possible prototypes for the development of new antiviral drugs.Molecules 2020, 25, 942 2 of 22 due to the ability of viruses to undergo rapid mutations, the mechanisms involved in developing resistance to antiviral drugs are activated in most cases [1,3]. As resistance toward antiviral drugs is becoming a global health threat, there is an intrinsic need to identify new scaffolds that are useful in discovering innovative, less toxic and highly active antiviral agents [3,6,7]. Nitrogen-Containing Heterocycles and Thiadiazole Ring in Biology and Medicinal ChemistryNitrogen-containing heterocycles are widely distributed in nature and are essential in vegetal and animal metabolism. They are found in nucleic acids, vitamins, antibiotics, alkaloids, etc. [8][9][10][11][12][13][14]. In addition, nitrogen-containing heterocycles are important targets for medicinal chemistry, as they are found in more than half of the commercially available drugs and can also act as versatile intermediates in the synthesis of complex products that exhibit outstanding biological activities [15]. Most of the nitrogen-containing heterocyclic compounds exhibit better biological activity than non-nitrogen compounds [12,16,17]. Currently, there are approximately 90 drugs approved for use in the treatment of nine human viral infections caused by human immunodeficiency virus (HIV), hepatitis B virus (HBV), hepatitis C virus (HCV), herpes simplex virus (HSV), Influenza virus, human cytomegalovirus (HCMV), varicella-zoster virus (VZV), respiratory syncytial virus (RSV) and human papillomavirus [18]. Most of these drugs (e.g., acyclovir, cidofovir, idoxuridine, nevirapine, pleconaril, ribavirin, etc.) are nitrogen heterocycle molecules [3,19].Five-membered aromatic systems with three heteroatoms at symmetrical positions, such as the 1,3,4-thiadiazole ring, have been extensively studied due to their pharmacological profile and physicochemical and pharmacokinetic properties. 1,3,4-Thiadiazole derivatives are known as compounds having significant and diverse biological activities such as antibacterial, antifungal, antitubercular [20], analgesic and anti-inflammatory [21,22], antidepr...

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Section: -10mentioning

confidence: 99%

Section: -10mentioning

confidence: 99%

Section: -16mentioning

confidence: 99%

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Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

Şerban

2020

Molecules

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“…Heterocyclic rings are important chemical scaffolds in the search for novel pesticides. Approximately 70% of pharmaceuticals and agrochemicals contain at least one heterocyclic moiety, and as one of the most important, the 1,3,4‐oxadiazole ring is reported to possess a wide variety of biological activities, including antibacterial, antifungal, antiviral, insecticidal and herbicidal . For instance, Guimarães et al .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Wen

Jian

Shang

et al. 2018

Pest Management Science

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BACKGROUND Natural stilbenes (especially resveratrol and its derivatives) are well‐known phytoalexins that are active against many plant diseases. However, oxidative degradation and low bioavailability limit their exogenous application as fungicides on crops. In this study, a new class of resveratrol‐inspired thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit was synthesized and the derivatives' antifungal activities against phytopathogenic fungi were investigated. RESULTS The results revealed that compounds 5h and 5j exhibited improved antifungal activity against Botrytis cinerea with median effective concentrations (EC50) of 168.5 and 155.4 µg mL−1, respectively, which were superior to the EC50 of resveratrol (263.1 µg mL−1). Compound 5j was shown to effectively control disease development in B. cinerea‐infected tomatoes in vivo. Notably, considerably abnormal mycelial morphology and increased cell membrane conductivity were observed in the presence of compound 5j. CONCLUSION A new class of thiophene‐containing stilbene derivatives was designed and synthesized. Bioassay results showed that compound 5j exhibited promising antifungal activity, suggesting practical potential for fungal disease control. © 2018 Society of Chemical Industry

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“…The prospect of pharmaceutical research remains the search for biologically active substances among molecules that combine heterocyclic moieties of different nature [1][2][3][4][5][7][8][9]. Examples of such fragments are 1,2,4-triazole and thiadiazole, which have significant synthetic and pharmacological potential [6].…”

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Synthesis and properties of some S-derivatives of 4-phenyl-5-((5-phenylamino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione

Gotsulya

Fedotov

2019

Current Issues in Pharmacy and Medicine: Science and Practice

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A -research concept and design; B -collection and/or assembly of data; C -data analysis and interpretation; D -writing the article; E -critical revision of the article; F -final approval of the article Studies in the field of chemistry and pharmacology of derivatives of thiadiazole and 1,2,4-triazole are promising and relevant, which is associated with significant success in creating new drugs based on them. The combination of these heterocycles in one molecule makes it possible to increase the probability of detecting substances with a certain type of biological activity among the synthesized compounds.The aim of the work was to optimize the synthesis and study of the properties of S-alkyl derivatives of 5-R-4-phenyl-1,2,4-triazole-3thione, containing a thiadiazole fragment in their structure, as well as the prediction of possible biological activity to rating the prospects of further studies in vivo and in vitro. Materials and methods.As a key starting reagent, 3-amino-1-phenylthiourea was used. Using the reaction between the starting reagent and carbon disulfide in DMF, thion was obtained, which was further alkylated with isopropyl chloroacetate. The resulting reaction product was then used for subsequent transformations using hydrazinolysis reactions, nucleophilic addition of phenylisothiocyanate and intramolecular alkaline heterocyclization. A number of S-derivatives of the obtained 4-phenyl-5-((5-phenylamino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were synthesized by the interaction with haloalkanes in the presence of an equivalent amount of alkali in alcoholic medium. The structure of the obtained compounds was confirmed by elemental analysis, 1 H NMR spectroscopy, and IR-spectrophotometry. The individuality of substances was established by high performance liquid chromatography. For the synthesized substances, an individual calculated screening was performed using the PASS Online ® software product.Results. The procedure for preparing 4-phenyl-5-((5-phenylamino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione was optimized. The optimal synthesis conditions were determined S-alkylderivatives of 4-phenyl-5-((5-phenylamino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thiol, the structure was established the obtained substances and their physical properties were studied. With the help of computer-assisted prediction Pass Online ® , a promising direction for further studies of the biological activity of the target reaction products was determined. Conclusions.A series of S-alkylderivatives of 4-phenyl-5-((5-phenylamino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione were obtained, the structure of these compounds was confirmed by physical-chemical methods of analysis. At the next stages of the study, it would be planned to establish indicators of the antimicrobial activity of the synthesized substances. Синтез і властивості деяких S-похідних 4-феніл-5-((5-феніламіно-1,3,4-тіадіазол-2-ілтіо)метил)-1,2,4-тріазол-3-тіону C. O. Федотов, А. С. ГоцуляДослідження в галуз...

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Synthesis and Biological Activities of Ethyl 2-(2-pyridylacetate) Derivatives Containing Thiourea, 1,2,4-triazole, Thiadiazole and Oxadiazole Moieties

Cited by 19 publications

References 45 publications

Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Synthesis and properties of some S-derivatives of 4-phenyl-5-((5-phenylamino-1,3,4-thiadiazole-2-ylthio)methyl)-1,2,4-triazole-3-thione

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