Poster presentation
272
SYNTHESIS OF DERIVATIVES OF LAGOXILIN WITH
PHTHALIC ANHYDRIDE
F.A. Sobirova, R.S. Esanov, A.D. Matchanov
Institute of Bioorganic Chemistry named after acad. A.S. Sadykov
Academy of Sciences of the Republic of Uzbekistan, Uzbekistan, Mirzo Ulugbek str.,
83, Tashkent, 100125
A number of biologically active compounds have been isolated from the plant
Lagochilus inebrians Bge
,
a representative of the
Lamiaceae
family, whose aqueous
decoctions and tinctures are used for various bleeding, colds and allergies, and their
physico-chemical parameters and spectral properties have been determined studied. The
literature also shows that the main biologically active substance of the plant
Lagochilus
inebrians Bunge
is the diterpenoid lagochiline (3,16,17,18-tetrahydroxy-9,13-
epoxylabdan).
Today, it is important to look for anticoagulants and hemostatic agents among 1,4-
dicarboxylic acid derivatives, since the literature reports that carboxylic acid amides and
hydrazides have hemostatic and anticoagulant effects. Amides and hydrazides of
phthalic acid are obtained by certain methods from phthalic anhydride or
tetrachlorophthalic acid. Dicarboxylic acids are also important in plant life. They have
not
only direct, but also secondary action. In particular, the immunobiological activity
of terpenes promotes the activation of the phagocytosis process, and together with
succinic acid improves the cellular and humoral
control of neutrophils and
macrophages. Based on these data, we set the task of carrying out the chemical
synthesis of 3,16,17,18-tetrahydroxy-9,13-epoxylabdan (lagoсhilin), which is the main
component of the plant
Lagochilus inebrians Bunge
, with
some representatives of a
number of dicarboxylic acids, especially phthalic, glutaric and succinic anhydrides. The
chemical synthesis of lagochilin with anhydrides of dicarboxylic acids was carried out
in an absolute pyridine medium at the boiling point of pyridine. The course of the
reaction was monitored by the TLC method. At the end of the reaction, pyridine was
neutralized with a cold solution of hydrochloric acid. Some physico-chemical
parameters of the synthesized substances have been studied. At the end of the reaction,
pyridine was neutralized with a cold solution of hydrochloric acid. Some physico-
chemical parameters of the synthesized substances have been studied. Mono-, di-, tri-,
tetra- , derivatives of lagochilin have
a light yellow oily nature, insoluble in water. In
our work, we took their sodium salts to ensure good solubility of esters in water. In
addition, some physico-chemical parameters of the synthesized compounds were
studied. in the IR - ν = (-C=O) 1750-1600; (C–O–C) 1450-1250, ν = (-ОН) 3500-3000;
ν = (-СН
2,
–CH
3
)2900-2800. When analyzing the UV spectrum of the sodium
salt of lagoxylin ester based on phthalic anhydride in the water:acetonitrile (1:1) system,
an intense absorption maximum appears, corresponding to the n→p* transition in the
UV spectrum of phthalic anhydride. at wavelengths of 238 and 293 nm. In the UV
spectrum of the sodium
salt of LgTF, a “hypsochromic” shift from 293 nm to 11 nm
was observed; simultaneously with a “hypsochromic” shift by 6 nm, a “hyperchromic”
effect was observed at an absorption maximum at 238 nm.