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

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

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.

Full Text

Restricted Access

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

References

  1. Чиряпкин А.С. // Juvenis Scientia. 2022. Т. 8. № 5. С. 16. doi: 10.32415/jscientia_2022_8, 5,_16-30
  2. Varghese B., Al-Busafi S.N., Suliman F.O., Al-Kindy S.M.Z. // RSC Adv. 2017. Vol. 7. N 74. P. 46999. doi: 10.1039/c7ra08939b
  3. Kumar S., Bawa S., Drabu S., Kumar R., Gupta H. // Recent Pat. Antiinfect. Drug Discov. 2009. Vol. 4. N 3. P. 154. doi: 10.2174/157489109789318569
  4. Nehra B., Rulhania S., Jaswal S., Kumar B., Singh G., Monga V. // Eur. J. Med. Chem. 2020. Vol. 205. P. 112666. doi: 10.1016/j.ejmech.2020.112666
  5. Matiadis D., Sagnou M. // Int. J. Mol. Sci. 2020. Vol. 21. N 15. P. 5507. doi: 10.3390/ijms21155507
  6. Deng H., Yu Z.Y., Shi G.Y., Chen M.J., Tao K., Hou T.P. // Chem. Biol. Drug Des. 2012. Vol. 79. N 3. P. 279. doi: 10.1111/j.1747-0285.2011.01308.x
  7. Машковский М.Д. Лекарственные средства. М.: Новая волна, 2010. С. 851.
  8. Guglielmi P., Carradori S., Poli G., Secci D., Cirilli R., Rotondi G., Chimenti P., Petzer A., Petzer J.P. // Molecules. 2019. Vol. 24. N 3. Р. 484. doi: 10.3390/molecules24030484
  9. Исаханян А.У., Акопян Н.З., Овасян З.А., Григорян Г.С., Мхитарян Р.П., Аракелян А.Г., Сафарян А.С., Мурадян Р.Е., Паносян Г.А., Арутюнян А.А. // ЖОХ. 2023. Т. 93. № 9. С. 1335; Isakhanyan A.U., Hakobyan N.Z., Hovasyan Z.A., Grigoryan G.S., Mkhitaryan R.P., Aracelyan H.G., Safaryan A.S., Muradyan R.E., Panosyan Н.A., Harutyunyan A.A. // Russ. J. Gen. Chem. 2023. Vol. 93. N 9. P. 2210. doi: 10.1134/S1070363223090037
  10. Lakowicz J.R. Principles of Fluorescence Spectroscopy. New York: Springer, 2006. P. 954. doi: 10.1007/978-0-387-46312-4
  11. Brouwer A.M. // Pure Appl. Chem. 2011. Vol. 83. N 12. P. 2213. doi: 10.1351/PAC-REP-10-09-31
  12. Shivananda M.K., Holla B.S. // J. Chem. Pharm. Res. 2017. Vol. 9. N 6. P. 1.

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Scheme 1

Download (389KB)
Indexing metadata
3. Fig. 1. Electronic absorption spectra of compounds 7-10 (1-4) in DMFA solutions (c = 2·10-5 mol/L)

Download (125KB)
Indexing metadata
4. Fig. 2. Electronic absorption spectra of compounds 11 (1) and 12 (2) in DMFA solutions (c = 5·10-5 mol/L)

Download (83KB)
Indexing metadata
5. Fig. 3. Electronic absorption spectra of compounds 14-17 (1-4) in DMFA solutions (c = 2·10-5 mol/L)

Download (110KB)
Indexing metadata
6. Fig. 4. Electronic absorption spectra of compounds 18-21 (1-4) in DMFA solutions (c = 5·10-5 mol/L)

Download (112KB)
Indexing metadata
7. Fig. 5. Fluorescence spectra of samples 7-10 (1-4) in DMFA solutions (excitation slit width - 5 nm, emission slit width - 5 nm)

Download (113KB)
Indexing metadata
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)

Download (85KB)
Indexing metadata
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)]

Download (140KB)
Indexing metadata
10. Fig. 8. Fluorescence spectra of samples 18-21 (1-4) in DMFA solutions (excitation slit width - 10 nm, emission slit width - 10 nm)

Download (120KB)
Indexing metadata
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)

Download (113KB)
Indexing metadata
12. Fig. 1

Download (30KB)
Indexing metadata
13. Fig. 2

Download (28KB)
Indexing metadata
14. Fig. 3

Download (31KB)
Indexing metadata
15. Fig. 4

Download (28KB)
Indexing metadata
16. Fig. 5

Download (29KB)
Indexing metadata
17. Fig. 6

Download (33KB)
Indexing metadata
18. Fig. 7

Download (33KB)
Indexing metadata
19. Fig. 8

Download (34KB)
Indexing metadata
20. Fig. 9

Download (35KB)
Indexing metadata
21. Fig. 10

Download (37KB)
Indexing metadata
22. Fig. 11

Download (32KB)
Indexing metadata
23. Fig. 12

Download (33KB)
Indexing metadata
24. Fig. 13

Download (34KB)
Indexing metadata
25. Fig. 14

Download (33KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences