Mass-spectrometric fragmentation of sodium 2-(4-methyl-5-(thiophene-2-yl)-4H-1,2,4-triazole-3-ylthio)acetate

Authors

  • V. A. Salionov
  • B. A. Varynskyi
  • V. V. Parchenko

DOI:

https://doi.org/10.14739/2310-1210.2015.5.53774

Keywords:

1, 2, 4-triazoles, Mass Spectrometry, High Performance Liquid Chromatography, Ionization In Electrospray

Abstract

The study of physical and chemical characteristics and establishing patterns of mass spectrometric fragmentation are the actual tasks of modern pharmaceutical science, have both scientific interest and practical importance.

Aim. The purpose of our experiment was to confirm the identity and study patterns of mass spectrometric decomposition for sodium 2-(4-methyl-5-(thiophene-2-yl) -4H-1,2,4-triazoles-3-ilthio) acetate.

Methods and results. The study was carried out on the apparatus LC MS / MS: LTQ Orbitrap. After completing MS scan, it has been established that the maximum peak in the chromatogram corresponds protonated ion 2-(4-methyl-5-(thiophene-2-yl)-4H-1,2,4-triazoles-3-ylthio)acetic acid m/z 256.0208, and empirical formula test compound - C9H9N3O2S2. MS/MS MH+ analysis showed that protonated molecule of the 2-(4-methyl-5-(thiophene-2-yl)-4H-1,2,4-3-triazole-3-ylthio)acetic acid under voltage in contact with molecules of helium in the collision cell was disintegrated from m/z 256.0208 into some fragments. The first time the mass spectrometric investigation sodium 2-(4-methyl-5-(thiophene-2-yl)-4H-1,2,4-triazoles-3-ylthio) acetate has been undertaken.

Conclusions. It has been established that the fragmentation of the molecule initially occurs with the dissociation of water molecule from carboxyl group. Under the influence of gas the next to come off may be a carboxyl group. In course of further dissociation the bond between the sulfur atom and acetic residue is destroyed or disruption of a covalent bond between sulfur and carbon of 1,2,4-triazole occurs.

 

References

Salionov, V. O., Pruhlo, Ye. S., Panasenko, O. I., & Knysh, Ye. H. (2013). Aktoprotektorna aktyvnist' pokhidnykh 2-(4-R-3-(tiofen-2-il)-4N-1,2,4-triazol-3-iltio)atsetatnykh kyslot [Actoprotective activity of derivatives of 2-(4-R-3-(thiophene-2-yl)-4H-1,2,4-triazol-3-iltio)acetic acid]. Zaporozhskij medicinskij zhurnal, 4(79), 51–53. [in Ukrainian].

Varynskyi, B. O. (2015). Optymizatsiia umov detektuvannia riadu 1,2,4-triazol-3-il-tioatsetatnykh kyslot ta yikh solei metodom VERKh-ESI-MS [Optimization of detecting a number of conditions 1,2,4-triazoles-3-yl-tioatsetatnyh acids and their salts by HPLC-ESI-MS]. Odeskyi medychnyi zhurnal, 4, 17–21. [in Ukrainian].

Varynskyi, B. O. (2015). Rozvytok VERKh-MS yak metodu otsiniuvannia chystoty i pidtverdzhennia molekuliarnoii masy novykh bioaktyvnykh rechovyn [Development of HPLC-MS as a method of evaluating the purity and confirm molecular mass of new bioactive compounds]. Aktualni pytannia farmatsevtychnoi i medychnoi nauky ta praktyky, 2, 85–88. [in Ukrainian].

Vulfson, N. S., Zaikin, V. G., & Mikaya, A. I. (1986) Mass-spektry organicheskikh soedinenij [Mass spectra of organic compounds]. Moscow. [in Russian].

Bushueva, I. V., Berezovskij, A. V., Knysh, Ye. H., & Panasenko, O. I. (2014). Zastosuvannia preparatu «Avesstym» dlia pidvyshchennia efektyvnosti vaktsynoprofilaktyky ta vplyv preparatu na rezystentnist' kurchat [Use of the drug "Avesstym" to improve vaccination and effects on the resistance of chickens]. Science Rise, 2014, 1(4), 94–97. [in Ukrainian].

Kazicina, L. A. (1979) Primenenie UF-, IK-, YaMR- i MASS-spektroskopii v organicheskoj khimii [Application of UV, IR, NMR and mass spectrometry in organic chemistry]. Moscow. [in Russian].

Kaplaushenko, A. H. (2013). Doslidzhennia zi stvorennia novoho oryhinal'noho vitchyznianoho likars'koho zasobu na osnovi 1,2,4-triazolu [Research on the creation of new original domestic drug based on 1,2,4-triazoles]. Naukovyi zhurnal MOZ Ukrainy, 2(3), 115–118. [in Ukrainian].

Iradyan, M. A., Iradyan, N. S., Grigoryan, R. T., & Panosyan, G. A. (2013). Metilovye e′firy i 5-(4N-1,2,4-triazol-3-ilsulfanil-metil)-furan-2-karbonovye kisloty. Sintez i mass-spektrometricheskoe issledovanie [Methyl ester and 5- (4H-1,2,4-triazol-3-ylsulfanyl-methyl)-furan-2-carboxylic acid. Synthesis and mass spectrometric investigation]. Himicheskiy zhurnal Armenii, 66(4), 636–647. [in Armenia].

Knysh, E. G., Parchenko, V. V., & Panasenko, A. I. (patentee) (2015). Veterinarnyj protivovirusnyj preparat [Pat. 2561674 Russia, IPC С 07 D 249/00. Veterinary antiviral drug. №2014102571/15. – declared 27.01.2015; published 27.08.2015. Bulleten′, 24. [in Russian].

Salionov, V. O., Panasenko, O. I., & Knysh, Ye. H. (2012). Syntez, fizyko-khimichni vlastyvosti 2-(4-R-5-(tiofen-2-il)-4N-1,2,4-triazol-3-iltio)atsetatnykh kyslot ta yikh solei [Synthesis, physico-chemical properties of 2-(4-R-5-(thiophene-2-yl) -4Н-1,2,4-triazol-3-iltio)acetic acids and its salts]. Ukrainskyi biofarmatsevtychnyi zhurnal, 5–6, 114–117. [in Ukrainian].

Song, S. H., Jun, S. H., Park, U. K., Yoon, Y., Lee, J. H., Kim, J. Q., & Song, J. (2007) Simultaneous determination of first-line anti-tuberculosis drugs and their major metabolic ratios by liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom, 21, 1331–1338.

Downloads

How to Cite

1.
Salionov VA, Varynskyi BA, Parchenko VV. Mass-spectrometric fragmentation of sodium 2-(4-methyl-5-(thiophene-2-yl)-4H-1,2,4-triazole-3-ylthio)acetate. Zaporozhye Medical Journal [Internet]. 2015Nov.20 [cited 2024Dec.26];17(5). Available from: http://zmj.zsmu.edu.ua/article/view/53774

Issue

No. 5 (2015): Zaporozhye medical journal

Section

Problems of pharmacy

License

Authors who publish with this journal agree to the following terms:

    1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.  Лицензия Creative Commons
    2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
    3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access)