New method for the synthesis of difficultly available sterically hindered tritium-labeled pyridinium derivatives

Щепина, Н. Е.; Аврорин, В. В.; Badun, G. A.; Федосеев, В. М.; Lewis, S. B.

doi:10.1007/s10593-010-0544-8

Cited by 8 publications

(4 citation statements)

References 34 publications

(31 reference statements)

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“…In either case, hydrogen replacement by its radioactive tritium isotope is not expected to cause any changes to the biological activity of the analog 1. Therefore, the nuclear-chemical method of synthesis of tritium labelled heterocyclic derivatives[ 34 35 36 37 38 ] developed by our research team can potentially produce N -phenyl-[f]-benzoquinaldinium salt labelled with affixed (non-exchangeable) tritium atom at para -position of the phenyl ring. This analog, in turn, can serve as a highly sensitive biomarker for the elucidation of molecular bases of the compound antimycotic activity.…”

Section: Discussionmentioning

confidence: 99%

Antifungal Activity of N-Arylbenzoquinaldinium Derivatives against a Clinical Strain of M. Canis

Shchepina,

Alexandrova,

Balandina

et al. 2023

Indian Journal of Dermatology

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Background: Microsporum canis (Bodin, 1902) is a dermatophyte, which is widely represented in the developing and the developed world alike. Commonly transmitted from domestic animals it is particularly dangerous for immunosuppressed patients due to AIDS, cancer or transplant surgery. Search for new perspective antimycotic derivatives becomes an urgent task in the disease containment. Previously, several quinolinium analogs were screened for their antibacterial activity ( E. coli, St. aurous ) by our research team. Furthermore, some N- phenylbenzoquinaldinium derivatives have shown antifungal activity against Candida albicans and Candida krusei . Aims: In this study, we sought to investigate fungicidal properties of N- arylbenzoquinaldinium derivatives against a clinical strain of Microsporum canis for future medicinal applications. Materials and Methods: N- phenyl-[f]-benzoquinaldinium salts were prepared by a variation of the previously described technique and tested against a clinical strain of the fungus of Microsporum canis 114 harvested from pathogenic material of a patient (Perm, Russia, 2014). Results: N- phenyl-[f]-benzoquinaldinium tetrafluoroborate has shown antifungal activity par to (or exceeding) that of commercially available medication. Moreover, this benzoquinaldinium analog can be potentially labelled with tritium by our nuclear-chemical method, making it amenable for the sensitive pharmacokinetic studies. Conclusions: N -phenyl-[f]-benzoquinaldinium tetrafluoroborate has been shown as a promising compound for the further development of potent antifungal agents as well as radiotracers for further elucidation of biological pathways of antifungal activity.

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Section: Discussionmentioning

confidence: 99%

Antifungal Activity of N-Arylbenzoquinaldinium Derivatives against a Clinical Strain of M. Canis

Shchepina,

Alexandrova,

Balandina

et al. 2023

Indian Journal of Dermatology

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“…Previously, we have used the elaborated nuclear-chemical method for the detailed investigations of the ion–molecular reactions of pyridine and quinoline derivatives [15-17]. By these investigations it was shown that with the application of nucleogenic phenyl cations (cations generated by the processes of tritium β-decay), unusual direct phenylation of nitrogen atom in pyridine ring might be realized.…”

Section: Methodsmentioning

confidence: 99%

Pathways of ion–molecular interactions of nucleogenic phenyl cations with the nucleophilic centers of picolines

Щепина

Аврорин

Бадун

et al. 2012

Organic and Medicinal Chemistry Letters

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BackgroundThe nuclear-chemical method brought unique opportunity for synthesis of unknown and hardly available organic compounds. Presence of tritium labeling allows one-step preparation of radioactive markers for the investigation of chemical and biological processes.MethodsThe ion–molecular reactions of nucleogenic phenyl cations with 4-picoline have been carried out. The phenyl cations were generated by spontaneous tritium β-decay within the tritium-labeled benzene. Both additions to the nitrogen and substitutions about the aromatic ring were able to be studied simultaneously.ResultsUnusual substitutions on both the α- and β-positions of the ring system have been revealed.ConclusionBy unknown direct phenylation of nitrogen atom tritium-labeled N-phenylpicolinium derivatives, perspective biological markers have been synthesized.

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“…Owing to this the development of easy and unusual methods for synthesis of new 1,4-diazine derivatives along with tritium labeling becomes an urgent task. Previously we have applied the elaborated nuclear-chemical method based on the consequences of tritium -decay for the one-step preparation of unknown and hardly available derivatives of monoazines, effective tritium labeled biological markers [37][38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Nuclear-Chemical Synthesis of 1,4-Diazine Quaternary Salts

Щепина¹,

Аврорин²,

Badun³

2013

OJSTA

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New method for the synthesis of difficultly available sterically hindered tritium-labeled pyridinium derivatives

Cited by 8 publications

References 34 publications

Antifungal Activity of N-Arylbenzoquinaldinium Derivatives against a Clinical Strain of M. Canis

Antifungal Activity of N-Arylbenzoquinaldinium Derivatives against a Clinical Strain of M. Canis

Pathways of ion–molecular interactions of nucleogenic phenyl cations with the nucleophilic centers of picolines

Nuclear-Chemical Synthesis of 1,4-Diazine Quaternary Salts

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