The reactivity of propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids

Authors

  • O. M. Svechnikova Kharkiv National Pedagogical University named after G. S. Skovoroda, Ukraine
  • S. V. Kolisnyk National University of Pharmacy, Ukraine
  • O. F. Vinnyk Kharkiv National Pedagogical University named after G. S. Skovoroda, Ukraine
  • O. V. Kolisnyk National University of Pharmacy, Ukraine

DOI:

https://doi.org/10.24959/nphj.17.2169

Keywords:

reactivity, N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids

Abstract

The study of the reactivity of substances allows optimizing the conditions of their synthesis and creating mathematical models of the “structure-biological activity” relationship that enable to carry out the targeted search of compounds with a specified high level of the biological action.

Aim. To study the reactivity of propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids.

Materials and methods. The reactivity of propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids was studied in reversible conditions on the model of acid-base equilibria by the method of potentiometric titration.

Results and discussion. The ionization constants of 9 propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids indicate that these compounds are weak acids. Elongation of the methylene fragments in the amino acid groups of molecules decreases their acidity. In contrast to the length of the methylene fragments their branching and the presence of the substituents do not affect acidity of the esters studied. In the framework of the principle of linearity of free energies the effect of the length of the methylene chain in the amino acid fragment of the molecules of propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids was quantitatively assessed by Hammett equation.

Conclusions. It has been found that propyl esters of N-[(2-oxoindolin-3-ylidene)-2-oxiacetyl]amino acids have the functions of weak monobasic acids. Elongation of the polymethylene chain weakens ionization. The low sensitivity of the reaction center to elongation of the methylene chain has been identified.

Author Biographies

O. M. Svechnikova, Kharkiv National Pedagogical University named after G. S. Skovoroda

Doctor of Chemistry (Dr. habil.), professor, head of the Chemistry Department

S. V. Kolisnyk, National University of Pharmacy

Doctor of Pharmacy (Dr. habil.), professor of the Analytical Chemistry Department

O. F. Vinnyk, Kharkiv National Pedagogical University named after G. S. Skovoroda

Candidate of Chemistry (Ph.D.), associate professor of Department of Chemistry

O. V. Kolisnyk, National University of Pharmacy

Candidate of of Pharmacy (Ph.D.), associate professor of the Pharmaceutical Chemistry Department

References

Kolisnyk, S. V., Bolotov, V. V., Liashenko, O. V. (2009). Zhurnal orhanichnoi ta farmatsevtychnoi himii – Journal of Organic and Pharmaceutical Chemistry, 5 (4 (28)), 55–59.

Shatilov, O. V., Shtrygol, S. Yu., Kolisnyk, S. V., Bolotov, V. V. (2012). Bukovynskii medychnyi visnyk, 16 (3 (63)), 118–123.

Kolisnyk, S. V., Markina, А. Yu., Tiupka, Т. I. (2012). Farmatsevtychnyi chasopys , 2 (22), 25–29.

Markin, P. M., Kolisnyk, S. V., Kononenko, N. M., Markin, P. M. (2012). Visnyk farmatsii – News of Pharmacy, 1 (69), 70–72.

Albert, А., Serzhent, Е. (1964). Konstanty ionizatcii kislot i osnovanii. Мoscow: Khimiia, 214.

Lvovskii, Ye. N. (1988). Statisticheskie metody postroeniia empiricheskih formul. Мoscow: Vysshaiia shkola, 125.

Kolisnyk, S. V., Sviechnikova, О. М., Bolotov, V. V., Kurko, K. V. ( 2011). Ukrainskyi medychnyi almanakh – Ukrainian medical almanac, 14 (5), 97–99.

Palm, V. A. (1967). Osnovy kolichestvennoi teorii organicheskih soedinenii.Lvov: Khimiia, 356.

Downloads

Published

2017-06-16

Issue

No. 2(90) (2017)

Section

Synthesis and Analysis of Biologically Active Substances

License

Copyright (c) 2017 National University of Pharmacy

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International 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.
  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).