Reactivity of phenylanthranilic acids derivatives. Xxiii. Synthesis and acid-base properties of 4,5-dymethoxy-n-(2´-carboxyphenyl)anthranilic acids

Authors

  • S. G. Isaev National University of Pharmacy, Ukraine
  • O. M. Sviechnikova Kharkiv National Pedagogical University named after G.S.Skovoroda,
  • A. O. Devyatkina National University of Pharmacy, Ukraine
  • T. A. Kostina National University of Pharmacy, Ukraine
  • T. N. Svyatska Kharkiv National Pedagogical University named after G.S.Skovoroda, Ukraine

DOI:

https://doi.org/10.24959/ophcj.13.748

Keywords:

synthesis, reactivity, N-phenylanthranilic acid

Abstract

The alternative ways of synthesis of new 4,5-dymethoxy-N-(2´ carboxyphenyl)anthranilic acids have been considered nad new ways for their obtaining have been suggested. The structure of the compounds synthesized has been proven by the elemental analysis, IR- and NMR-spectroscopy. The purity has been controlled by the method of thin-layer chromatography. The reactivity of 4,5-dymethoxy-N-(2´-carboxyphenyl)anthranilic acids has been researched by studying the acid-base properties in the binary solvent of dioxane-water (60 vol% of dioxane). It has been found that the substances synthesized are dibasic subacids, which strength depends upon the nature and position of substituents. The quantitative assessment of the influence of substituents on two reactive centres of the acids synthesized has been carried out by the method of correlative analysis according to the Gamete equation. It has been proven that the reactive centres sensitivity is substantially different and dependent on the substituent distance. In addition, appearance of another reactive centre does not practically influence on sensitivity of the first one. It has been determined that the substances synthesized reveal the anti-inflammatory, analgesic, diuretic, bacteriostatic, and fungistatic effects. According to the classification by K.K. Sydorov the substances synthesized when introducing intragastrically belong to low-toxic compounds (DL50>3000 mg/kg).

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Published

2013-09-10

How to Cite

(1)
Isaev, S. G.; Sviechnikova, O. M.; Devyatkina, A. O.; Kostina, T. A.; Svyatska, T. N. Reactivity of Phenylanthranilic Acids Derivatives. Xxiii. Synthesis and Acid-Base Properties of 4,5-Dymethoxy-N-(2´-carboxyphenyl)anthranilic Acids. J. Org. Pharm. Chem. 2013, 11, 26-31.

Issue

Vol. 11 No. 3(43) (2013)

Section

Original Researches

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