Search for Monoamine Oxidase Inhibitors among Pyrazoline and Pyrimidine Derivatives and Studying Luminescent Properties of the Obtained Compounds

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Abstract

Cyclization of the (E)-3-aryl-1-(4-alkoxyphenyl)prop-2-en-1-ones with phenylhydrazine in an acidic medium leads to the 5-aryl-3-(4-alkoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazoles. Bubbling air through a solution of 5-(4-methoxyphenyl)-1-phenyl-3-(4-ethoxyphenyl)-4,5-dihydro-1H-pyrazole in ethylcellosolve resulted in an oxidation-dehydrogenation product, which characterized as the picrate of the corresponding pyrazole. The reaction of benzamidine and 4-methylbenzamidine hydrochlorides with substituted chalcones in а KOH–ethanol system leads to 2,4-diaryl-6-(4-alkoxyphenyl)pyrimidines. The luminescent and antimonoamine oxidase properties of the resulting systems were studied.

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About the authors

A. U. Isakhanyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

Author for correspondence.
Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0002-1713-4908
Armenia, Yerevan

N. Z. Hakobyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0002-3095-5938
Armenia, Yerevan

Z. A. Hovasyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0001-6698-7184
Armenia, Yerevan

G. S. Grigoryan

Yerevan State University

Email: gevsgrig@ysu.am
ORCID iD: 0000-0002-0675-735X
Armenia, Yerevan

R. P. Mkhitaryan

Yerevan State University

Email: gevsgrig@ysu.am
ORCID iD: 0009-0009-6277-2747
Armenia, Yerevan

D. L. Yesayan

Yerevan State University

Email: gevsgrig@ysu.am
ORCID iD: 0009-0008-7243-6248
Russian Federation, Yerevan

A. S. Grigoryan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0002-3834-3338
Russian Federation, Yerevan

H. V. Gasparyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0002-8555-3733
Russian Federation, Yerevan

Н. A. Panosyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0001-8311-6276
Russian Federation, Yerevan

A. A. Harutyunyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia

Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0003-0641-5453
Russian Federation, Yerevan

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Supplementary files

Supplementary Files
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1. JATS XML
2. Scheme 1

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3. Fig. 1. Electronic absorption spectra of compounds 7-10 (1-4) in DMFA solutions (c = 2·10-5 mol/L)

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4. Fig. 2. Electronic absorption spectra of compounds 11 (1) and 12 (2) in DMFA solutions (c = 5·10-5 mol/L)

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5. Fig. 3. Electronic absorption spectra of compounds 14-17 (1-4) in DMFA solutions (c = 2·10-5 mol/L)

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6. Fig. 4. Electronic absorption spectra of compounds 18-21 (1-4) in DMFA solutions (c = 5·10-5 mol/L)

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7. Fig. 5. Fluorescence spectra of samples 7-10 (1-4) in DMFA solutions (excitation slit width - 5 nm, emission slit width - 5 nm)

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8. Fig. 6. Fluorescence spectra of samples 11 (1) and 12 (2) in DMFA solutions (excitation slit width - 5 nm, emission slit width - 5 nm)

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9. Fig. 7. Fluorescence spectra of samples 14-17 (1-4) in DMFA solutions [excitation slit width - 5 (16 and 17), 10 nm (14 and 15), emission slit width - 5 (16 and 17), 10 nm (14 and 15)]

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10. Fig. 8. Fluorescence spectra of samples 18-21 (1-4) in DMFA solutions (excitation slit width - 10 nm, emission slit width - 10 nm)

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11. Fig. 9. Effect of compounds 7, 9-11, 13 on inhibition of MAO activity at a concentration of 1.0 μmol/mL as a percentage of control (indopan)

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12. Fig. 1

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13. Fig. 2

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14. Fig. 3

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15. Fig. 4

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16. Fig. 5

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17. Fig. 6

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18. Fig. 7

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19. Fig. 8

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20. Fig. 9

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21. Fig. 10

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22. Fig. 11

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23. Fig. 12

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24. Fig. 13

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25. Fig. 14

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