Synthesis and structure of novel benzisothiazole-tetrazolyl derivatives for potential application as nitrogen ligands

Frija, Luís M. T.; Fausto, Rui; Loureiro, Rui M. S.; Cristiano, Maria Lurdes Santos

doi:10.1016/j.molcata.2008.12.007

Cited by 35 publications

(12 citation statements)

References 27 publications

(28 reference statements)

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“…39 The compound has the important structural characteristic of being able to establish different types of intramolecular hydrogen bonds (NH · · · O or OH · · · N), depending on the tautomeric form. In turn, these different types of intramolecular interactions can be expected to influence the chemical behavior of the tautomers.…”

Section: Introductionmentioning

confidence: 99%

Tautomer Selective Photochemistry in 1-(Tetrazol-5-yl)ethanol

et al. 2010

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A combined matrix isolation FTIR and theoretical DFT/B3LYP/6-311++G(d,p) study of the molecular structure and photochemistry of 1-(tetrazol-5-yl)ethanol [1-TE] was performed. The potential energy surface landscapes of the 1H and 2H tautomers of the compound were investigated and the theoretical results were used to help characterize the conformational mixture existing in equilibrium in the gas phase prior to deposition of the matrices, as well as the conformers trapped in the latter. In the gas phase, at room temperature, the compound exists as a mixture of 12 conformers (five of the 1H tautomer and seven of the 2H tautomer). Upon deposition of the compound in an argon matrix at 10 K, only three main forms survive, because the low barriers for conformational isomerization allow extensive conformational cooling during deposition. Deposition of the matrix at 30 K led to further simplification of the conformational mixture with only one conformer of each tautomer of 1-TE surviving. These conformers correspond to the most stable forms of each tautomer, which bear different types of intramolecular H-bonds: 1H-I has an NH · · · O hydrogen bond, whereas 2H-I has an OH · · · N hydrogen bond. Upon irradiating with UV light (λ > 200 nm), a matrix containing both 1H-I and 2H-I forms, an unprecedented tautomer selective photochemistry was observed, with the 2H tautomeric form undergoing unimolecular decomposition to azide + hydroxypropanenitrile and the 1H-tautomer being photostable.

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Section: Introductionmentioning

confidence: 99%

Tautomer Selective Photochemistry in 1-(Tetrazol-5-yl)ethanol

et al. 2010

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“…Similarly, compound 9 (MTSB) was prepared by coupling 2 and 5-methyl-1,3,4-thiadiazole-2-thiol (8) (Scheme 1 (C)). All of the reactions proceeded smoothly under experimental protocols originally developed by us [56][57][58][59], affording crystalline products in reasonable to very good yields. Scheme 1.…”

Section: Chemistrymentioning

confidence: 99%

In Vitro Assessment of Antimicrobial, Antioxidant, and Cytotoxic Properties of Saccharin–Tetrazolyl and –Thiadiazolyl Derivatives: The Simple Dependence of the pH Value on Antimicrobial Activity

Frija

Ntungwe²,

Sitarek

et al. 2019

Pharmaceuticals

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The antimicrobial, antioxidant, and cytotoxic activities of a series of saccharin–tetrazolyl and –thiadiazolyl analogs were examined. The assessment of the antimicrobial properties of the referred-to molecules was completed through an evaluation of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values against Gram-positive and Gram-negative bacteria and yeasts. Scrutiny of the MIC and MBC values of the compounds at pH 4.0, 7.0, and 9.0 against four Gram-positive strains revealed high values for both the MIC and MBC at pH 4.0 (ranging from 0.98 to 125 µg/mL) and moderate values at pH 7.0 and 9.0, exposing strong antimicrobial activities in an acidic medium. An antioxidant activity analysis of the molecules was performed by using the DPPH (2,2-diphenyl-1-picrylhydrazyl) method, which showed high activity for the TSMT (N-(1-methyl-2H-tetrazol-5-yl)-N-(1,1-dioxo-1,2-benzisothiazol-3-yl) amine, 7) derivative (90.29% compared to a butylated hydroxytoluene positive control of 61.96%). Besides, the general toxicity of the saccharin analogs was evaluated in an Artemia salina model, which displayed insignificant toxicity values. In turn, upon an assessment of cell viability, all of the compounds were found to be nontoxic in range concentrations of 0–100 µg/mL in H7PX glioma cells. The tested molecules have inspiring antimicrobial and antioxidant properties that represent potential core structures in the design of new drugs for the treatment of infectious diseases.

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“…In recent years, we have designed tetrazole-saccharinates [ 17 , 18 , 19 , 20 ] and demonstrated their effective and selective chelation capabilities for Cu(II) [ 17 ]. It was also demonstrated that the ligands are non-toxic while their corresponding copper complexes proved highly cytotoxic toward several cancer cell lines, suggesting their application in chelant-based antineoplastic chemotherapy.…”

Section: Introductionmentioning

confidence: 99%

On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[d]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate

et al. 2021

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Aquatic contamination by heavy metals is a major concern for the serious negative consequences it has for plants, animals, and humans. Among the most toxic metals, Cd(II) stands out since selective and truly efficient methodologies for its removal are not known. We report a novel multidentate chelating agent comprising the heterocycles thiadiazole and benzisothiazole. 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[d]isothiazole 1,1-dioxide (AL14) was synthesized from cheap saccharin and characterized by different techniques, including single crystal X-ray crystallography. Our studies revealed the efficiency and selectivity of AL14 for the chelation of dissolved Cd(II) (as compared to Cu(II) and Fe(II)). Different spectral changes were observed upon the addition of Cd(II) and Cu(II) during UV-Vis titrations, suggesting different complexation interactions with both metals.

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Synthesis and structure of novel benzisothiazole-tetrazolyl derivatives for potential application as nitrogen ligands

Cited by 35 publications

References 27 publications

Tautomer Selective Photochemistry in 1-(Tetrazol-5-yl)ethanol

Tautomer Selective Photochemistry in 1-(Tetrazol-5-yl)ethanol

In Vitro Assessment of Antimicrobial, Antioxidant, and Cytotoxic Properties of Saccharin–Tetrazolyl and –Thiadiazolyl Derivatives: The Simple Dependence of the pH Value on Antimicrobial Activity

On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[d]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate

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