The reactivity of aromatic and heterocyclic derivatives of hydrazine. Vіі. The acid-base properties of substituted 5,7-dichloro-9-hydrazine acridine

Authors

  • A. O. Deviatkina National University of Pharmacy, Ukraine
  • O. M. Svechnikova Kharkiv National Pedagogical University, Ukraine
  • S. V. Kolisnyk National University of Pharmacy, Ukraine
  • N. P. Kobzar National University of Pharmacy, Ukraine
  • A. F. Vinnyk Kharkiv National Pedagogical University, Ukraine

DOI:

https://doi.org/10.24959/nphj.16.2060

Keywords:

substituted 5, 7-dichloro-9-hydrazine acridine, reactivity

Abstract

The reactivity of substituted 5,7-dichloro-9-hydrazine acridine that exhibit various pharmacological activity by studying acid-base equilibria in the ethanol-water binary solvent (50 mol % ethanol) at 250С using the method of potentiometric titration has been investigated. The values pK of the corresponding conjugate acids obtained for 7 compounds indicate that these compounds are very weak bases. Analysis of the impact of the nature and position of substituents in the heterocycle on the strength of the corresponding conjugate acids has shown that the acceptor substituents weaken basicity of 5,7-dichloro-9-hydrazine acridine, and donor substituents cause the opposite effect. The quantitative assessment of the influence of substituents in the molecule by Hammett equation within the principle of linearity of free energies with convincing statistical parameters has shown a low sensitivity of the reaction centre to structural changes in the molecule of 5,7-dichloro-9-hydrazine acridine. Using the correlation equation and the value pKBH+ experimentally obtained for 1-CH3 substituent the σ-constant of this substituent: σ(1-CH3) = 0.056 has been determined. The Hammett correlation equation is used to predict the acid-base properties of substituted 5,7-dichloro-9-hydrazine acridines and molecular design of more active pharmacophores.

Author Biographies

A. O. Deviatkina, National University of Pharmacy

Department of Medicinal Chemistry

O. M. Svechnikova, Kharkiv National Pedagogical University

Department of Chemistry

S. V. Kolisnyk, National University of Pharmacy

Department of Analytical Chemistry

N. P. Kobzar, National University of Pharmacy

Department of Medicinal Chemistry

A. F. Vinnyk, Kharkiv National Pedagogical University

Department of Chemistry

References

Альберт А. Константы ионизации кислот и оснований / А. Альберт, Е. Сержент. – М.: Химия, 1964-178 с.

Державна Фармакопея України/Державне підприємство «Науково-експертний фармакопейний центр». – 1-е вид. – Харків: РІРЕГ, 2001. – 556 с.

Ісаєв С.Г. // Ліки. – 2001. - №3/4. – С. 72-74.

Ісаєв С.Г., Свєчнікова О.М., Павлій О.І. // Вісник фармації – 2003. - №4(36). – С. 27-29.

Ісаєв С.Г. // Фармац. журн. – 1999. - №3. – С. 52-54.

Ісаєв С.Г., Яременко В.Д., Русакова Н.П. // Фармац. журн. – 2000. - №1. – С. 72-75.

Лабораторное руководство по хроматографии и смежным методам / Пер. с англ. – М.: Мир, 1982. – Т. 1. – 396 с.

Львовский Е.Н. Статистические методы построения эмпирических формул / Е.Н Львовский. – М.: Высш. Шк., 1988. – 125 с.

Мартиновский О.О., Панасенко Т.В., Панасенко О.І. // Вісник фармації. – 1999. – №2(20). – С. 44-46.

Мохамед Мохамед Мохмуд Барака. Синтез, физико-химические свойства и биологическая активность тио-, гидразинопроизводных 6-хлор-7-нитроакридина: Автореф. дис. … канд. фармац. наук. – Х., 1992. – 19 с.

Панасенко А.Н., Омельянчик Л.А., Панасенко Т.В. та ін. // Актуальні питання фармацевтичної та медичної науки та практики. – Запоріжжя., 1988. – Т. 2. – Вип. 2. – С. 60-63.

Свечникова Е.Н. // ЖОХ. – 1997. – Т. 67, вып. 1 – С. 138-140.

Свечникова Е.Н. // ЖОХ. – 1998. – Т. 67, вып. 6 – С. 1007-1008.

Свечникова Е.Н. // ЖОХ. – 1999. – Т. 68, вып. 5 – С. 865-866.

Свечникова Е.Н. // ЖОХ. – 2001. – Т. 71, вып. 5 – С. 848-849.

Свєчнікова О.М. Реакційна здатність, зв'язок структура-біологічна активність та використання похідних N-фенілантранілової кислоти та акридину. Автореферат дис.. на здобуття наук.ступеня докт.хім.н., Харків, 1999.-35 стор.

Таблицы констант скорости и равновесия гетеролитических органических реакций. – М.: ВИНИТИ, 1975. – Т. 1. – 396 с.

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Published

2016-03-11

Issue

No. 1(85) (2016)

Section

Synthesis and Analysis of Biologically Active Substances

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