Biologically active<i>halo</i>-substituted ferrocenyl thioureas: synthesis, spectroscopic characterization, and DFT calculations

Asghar, Faiza; Rana, Sadaf; Fatima, Saira; Badshah, Amin; Lal, Bhajan; Butler, Ian S.

doi:10.1039/c8nj00483h

Cited by 18 publications

(4 citation statements)

References 50 publications

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“…Following the same procedure, the following isothiocyanates were prepared: 2-bromobenzoyl isothiocyanate (1b), 75% yield; 4-methoxybenzoyl isothiocyanate (1c), 61% yield; 4-chlorobenzoyl isothiocyanate (1d), 64% yield, and 4bromobenzoyl isothiocyanate (1e), 78% yield. All compounds were confirmed by GC-MS analysis to be > 90% pure, with properties matching those previously published [15][16][17]. No attempts of further purification were made, due to their tendency to slowly decompose.…”

Section: Benzoyl Isothiocyanate (1a) a Representativesupporting

confidence: 76%

Organotellurium Chemistry: Synthesis and Properties of 2-Acylamino- and 2-Arylamino-1,3-benzotellurazoles

Smith¹,

Franklin²,

Goutierrez³

et al. 2019

AJHC

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Synthetic methods have been developed to prepare novel 1,3-benzotellurazoles carrying acylamino and arylamino moieties in position 2, in order to investigate their propensity to self-assemble to supramolecular structures. The targeted compounds were obtained in yields ranging from 44% to 67%, by reacting bis(2-aminophenyl) ditelluride with acyl-and aryl isothiocyanates, respectively, and subsequent reductive cyclization of the resulting thiourea derivatives. Seven novel 1,3benzotellurazole derivatives were prepared: 2-benzoylamino-1,3-benzotellurazole, 2-(4-chlorobenzoylamino)-1,3benzotellurazole, 2-(2-bromobenzoylamino)-1,3-benzotellurazole, 2-(4-bromobenzoylamino)-1,3-benzotellurazole, 2-(4methoxybenzoylamino)-1,3-benzotellurazole, 2-phenylamino-1,3-benzotellurazole, and 2-(4-chlorophenylamino-1,3benzotellurazole. A simplified protocol was employed to synthesize all acyl isothiocyanates needed for their preparation from benzoyl halide derivatives and potassium thiocyanate. The reductive cyclization of the intermediate thioureas was challenging, only the use of hydroxymethanesulfinate in the presence of elemental mercury provided synthetically useful product yields. A mechanism was proposed, consisting of the insertion of mercury into the Te-Te bond, followed by intramolecular nucleophilic attack of the thiocarbonyl moiety by the resulting insertion product. All 2-acylamino-1,3-benzotellurazoles are crystalline solids, which are stable to ambient light, air and moderate heat. A characterization of selected samples by X-ray crystallography indicated that they form dimers in solid state, resulting from hydrogen bonding between the exocyclic and endocyclic nitrogen atoms of two adjacent molecules. This sets them apart from 2-alkyl-and 2-aryl-1,3-benzotellurazoles, which are known to self-assemble into supramolecular wires.

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Section: Benzoyl Isothiocyanate (1a) a Representativesupporting

confidence: 76%

Organotellurium Chemistry: Synthesis and Properties of 2-Acylamino- and 2-Arylamino-1,3-benzotellurazoles

Smith¹,

Franklin²,

Goutierrez³

et al. 2019

AJHC

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“…Asghar and coworkers 69 synthesized a series of ferrocene-based thioureas 91a–i and characterized them by spectroscopic techniques. It was found that the incorporation of the ferrocenyl group into thioureas is responsible for their enhanced lipophilic character.…”

Section: Applicationsmentioning

confidence: 99%

Recent trends in chemistry, structure, and various applications of 1-acyl-3-substituted thioureas: a detailed review

et al. 2022

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“…It is widely known that thiourea derivatives have antibacterial activity against planktonic bacteria. 28,29 Instead, microorganisms have the ability to create biological films (biofilms), which are complex communities of bacteria adhered to either a living or inert surface. In this situation, bacteria are more immune system, disinfectant, and antibiotic resistant than planktonic cells.…”

Section: Introductionmentioning

confidence: 99%

Isosteric O/S exchange in carbonyl(thio)ureides: molecular interactions, structure, and bioactivity assays

Aguilar,

Cogollo,

Echeverría

et al. 2023

New J. Chem.

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Biologically activehalo-substituted ferrocenyl thioureas: synthesis, spectroscopic characterization, and DFT calculations

Abstract: The DNA binding affinity of ferrocenyl complexes explored by CV and UV ascertain them as noble DNA binders. The computational measurements correlate well with the outcomes of electrochemistry and bio-activities.

Cited by 18 publications

References 50 publications

Organotellurium Chemistry: Synthesis and Properties of 2-Acylamino- and 2-Arylamino-1,3-benzotellurazoles

Organotellurium Chemistry: Synthesis and Properties of 2-Acylamino- and 2-Arylamino-1,3-benzotellurazoles

Recent trends in chemistry, structure, and various applications of 1-acyl-3-substituted thioureas: a detailed review

Isosteric O/S exchange in carbonyl(thio)ureides: molecular interactions, structure, and bioactivity assays

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