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4 results on '"Sazonov, K. D."'

1. SYNTHESIS OF NEW DERIVATIVES OF INDENOQUINOXALINECARBOXYLIC ACIDS WITH AMINES AND IN SILICO PREDICTION OF THEIR BIOLOGICAL ACTIVITY.

Author

Sazonov, K. D., Ishkov, Yu. V., and Shevchenko, O. V.

Subjects
CHEMICAL synthesis, DRUG target, ACID derivatives, BLOOD-brain barrier, ETHYL group
Abstract

The corresponding amide derivatives of 11-oxoindeno[1,2-b]quinoxaline-6-carboxylic acid were synthesized in good yields by interaction with amines (N,N-dimethylpropane-1,3-diamine, novocaine, 2,6-dimethylpyrimidin-4-amine). The technique is simple and well reproducible. It provides preliminary activation of the carboxyl group by ethyl ester of monochlorocarbonic acid with its conversion to anhydride in chloroform in the presence of triethylamine. Anhydride gently reacts with amines under the same conditions without preliminary isolation to form the corresponding derivatives. Physicochemical and pharmacokinetic properties of the synthesized compounds were predicted using the ADMETlab 3.0 program. All tested compounds corresponded to Lipinsky's rule and can be classified as «drug-like». Pharmacokinetic parameters (clearance, half-life, ability to penetrate the blood-brain barrier and be absorbed in the intestine) indicated the possibility of their oral use. Computer screening using the PharmMapper database confirmed the ability of the synthesized compounds to bind to a number of biological targets involved in cell replication and division. This indicates their potential for intercalation into DNA for the treatment of viral infections and tumors and the prospects for their further studies using in vitro methods. [ABSTRACT FROM AUTHOR]

Published
2024
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2. 6- ТА 7-АМІНОМЕТИЛ-11H-ІНДЕНО[1,2-b]ХІНОКСАЛІН-11-ОНИ – СИНТЕЗ, АФІНІТЕТ ДО ДНК ТА ТОКСИЧНІСТЬ

Author

Duma, H. I., Sazonov, K. D., Liakhov, L. S., Toporov, S. V., and Liakhov, S. A.

Subjects
aminomethyl-11H-indeno[1,2-b]quinoxalin-11-ones, synthesis, intercalation, affinity, toxicity, хімія, chemistry, амінометил-11H-індено[1,2-b]хіноксалін-11-они, синтез, інтеркаляція, афінітет, токсичність
Abstract

The actuality of the antivirals design and synthesis capable to the reproduction inhibition of emerging and mutated viruses is now especially evident against the background of the SARSCoV-2 outbreak in the world. New 6- and 7-aminomethyl-11H-indeno[2,3-b]quinoxalin-11-ones (AMIQ) were synthesized to obtain new DNA intercalators with the expected antiviral activity caused of their ability to intercalate DNA. The synthesis was performed by condensation of ninhydrin with 2,3- and 3,4-diaminotoluenes, followed by N-bromosuccinimide bromination and amino-debromination by the action of an excess of secondary amines on the corresponding bromomethyl derivatives. The structures of the synthesized compounds were confirmed by mass spectrometry and IR-spectroscopy. The molecular ion peaks present at the mass spectra of all compounds, m/z values of fragmentation ions correspond to the trivial fragmentation rote; absorption bands in the IR spectra correspond to the presented functional groups. All synthesized AMIQ demonstrate the ability to compete with ethidium bromide for DNA binding sites, which is typical for DNA intercalators. The AMIQ affinity to DNA was investigated by this method and appeared as close to that of amixine (lgKa =5.7 – 6.8). The amino groups’ structure and the position of the substituent do not significantly affect the affinity at P < 0.05. AMIQ toxicity was evaluated in a 24-hour toxicity test against A. parthenogenetica, in which these compounds were less toxic than amixine in most cases with –lgLC50 values less than 4. Obtained results testify to perspectivity of the further AMIQ and their analogs investiagations as potential broad spectra antiviral agents., Синтезовані нові похідні інденохіноксаліну – 6-амінометил-11H-індено[1,2-b]хіноксалін-11-они та 7-амінометил-11H-індено[1,2-b]хіноксалін-11-они, показано, що вони є інтеркаляторами ДНК з афінітетом на рівні противірусного агенту та індуктору інтерферону аміксину та в цілому менш токсичні за нього, що зумовлює доцільність їх подальшого дослідження як потенційних противірусних агентів.

Published
2020

4. 6- AND 7-AMINOMETHYL-11H-INDENO[1,2-b]QUINOXALINE-11-ONES – SYNTHESIS, DNA AFINITY AND TOXICITY

Author

Duma, H. I.; Фізико-хімічний інститут ім. О. В. Богатського НАН України, відділ медичної хімії, Sazonov, K. D.; Одеський національний університет імені І. І. Мечникова, Liakhov, L. S.; Фізико-хімічний інститут ім. О. В. Богатського НАН України, відділ медичної хімії, Toporov, S. V.; Одеський національний університет імені І. І. Мечникова, Liakhov, S. A.; Фізико-хімічний інститут ім. О. В. Богатського НАН України, відділ медичної хімії, Duma, H. I.; Фізико-хімічний інститут ім. О. В. Богатського НАН України, відділ медичної хімії, Sazonov, K. D.; Одеський національний університет імені І. І. Мечникова, Liakhov, L. S.; Фізико-хімічний інститут ім. О. В. Богатського НАН України, відділ медичної хімії, Toporov, S. V.; Одеський національний університет імені І. І. Мечникова, and Liakhov, S. A.; Фізико-хімічний інститут ім. О. В. Богатського НАН України, відділ медичної хімії

Abstract

The actuality of the antivirals design and synthesis capable to the reproduction inhibition of emerging and mutated viruses is now especially evident against the background of the SARSCoV-2 outbreak in the world. New 6- and 7-aminomethyl-11H-indeno[2,3-b]quinoxalin-11-ones (AMIQ) were synthesized to obtain new DNA intercalators with the expected antiviral activity caused of their ability to intercalate DNA. The synthesis was performed by condensation of ninhydrin with 2,3- and 3,4-diaminotoluenes, followed by N-bromosuccinimide bromination and amino-debromination by the action of an excess of secondary amines on the corresponding bromomethyl derivatives. The structures of the synthesized compounds were confirmed by mass spectrometry and IR-spectroscopy. The molecular ion peaks present at the mass spectra of all compounds, m/z values of fragmentation ions correspond to the trivial fragmentation rote; absorption bands in the IR spectra correspond to the presented functional groups. All synthesized AMIQ demonstrate the ability to compete with ethidium bromide for DNA binding sites, which is typical for DNA intercalators. The AMIQ affinity to DNA was investigated by this method and appeared as close to that of amixine (lgKa =5.7 – 6.8). The amino groups’ structure and the position of the substituent do not significantly affect the affinity at P < 0.05. AMIQ toxicity was evaluated in a 24-hour toxicity test against A. parthenogenetica, in which these compounds were less toxic than amixine in most cases with –lgLC50 values less than 4. Obtained results testify to perspectivity of the further AMIQ and their analogs investiagations as potential broad spectra antiviral agents., Синтезовані нові похідні інденохіноксаліну – 6-амінометил-11H-індено[1,2-b]хіноксалін-11-они та 7-амінометил-11H-індено[1,2-b]хіноксалін-11-они, показано, що вони є інтеркаляторами ДНК з афінітетом на рівні противірусного агенту та індуктору інтерферону аміксину та в цілому менш токсичні за нього, що зумовлює доцільність їх подальшого дослідження як потенційних противірусних агентів.

Published
2020

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