Pyrazolines and pyrimidines based on (E)-1-(4-pentyloxyphenyl)-3-arylprop-2-en-1-ones. Synthesis, docking study and luminescent properties
- Authors: Isakhanyan A.U.1, Ovasyan Z.A.1, Grigoryan G.S.2, Mkhitaryan R.P.2, Gabrielyan L.S.2, Panosyan G.A.1, Dangyan M.Y.1, Sargsyan A.S.3, Hambardzumyan A.A.3, Harutyunyan A.A.1
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Affiliations:
- Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia
- Yerevan State University
- Scientific and Production Center “Armbiotechnology” of the National Academy of Sciences of the Republic of Armenia
- Issue: Vol 94, No 5 (2024)
- Pages: 569-582
- Section: Articles
- URL: https://medjrf.com/0044-460X/article/view/667399
- DOI: https://doi.org/10.31857/S0044460X24050048
- EDN: https://elibrary.ru/FKOGQZ
- ID: 667399
Cite item
Abstract
(E)-1-(4-Pentyloxyphenyl)-3-(aryl)prop-2-en-1-ones were obtained by condensation of 1-(4-pentyloxyphenyl)ethanone with aromatic aldehydes in an aqueous ethanol solution in the presence of NaOH. The corresponding pyrazoline derivatives were prepared by cyclization of substituted chalcones with phenylhydrazine in an acidic medium, while 2,4,6-triaryl-substituted pyrimidines were produced in the case of benzamidine hydrochloride in the KOH–ethanol. It was found that all synthesized pyrazoline derivatives exhibit pronounced luminescent properties. A docking study of the compounds was carried out against four types of receptors.
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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
Z. A. Ovasyan
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: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0002-0675-735X
Armenia, Yerevan
R. P. Mkhitaryan
Yerevan State University
Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0009-0009-6277-2747
Armenia, Yerevan
L. S. Gabrielyan
Yerevan State University
Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0002-9212-9682
Armenia, Yerevan
G. 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
Armenia, Yerevan
M. Yu. Dangyan
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: 0000-0001-7703-1591
Armenia, Yerevan
A. S. Sargsyan
Scientific and Production Center “Armbiotechnology” of the National Academy of Sciences of the Republic of Armenia
Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0001-7249-233X
Armenia, Yerevan
A. A. Hambardzumyan
Scientific and Production Center “Armbiotechnology” of the National Academy of Sciences of the Republic of Armenia
Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0001-9526-7768
Armenia, 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
Armenia, Yerevan
References
- Morsy N.M., Hassan A.S. // Eur. J. Chem. 2022. Vol. 13. N 2. P. 241. doi: 10.5155/eurjchem.13.2.241-252.2245
- Suwito H., Jumina, Mustofa, Pudjiastuti P., Fanani M.Z., Kimata-Ariga Y., Katahira R., Kawakami T., Fujiwara T., Hase T., Sirat H.M., Puspaningsih N.N.T. // Molecules. 2014. Vol. 19. P. 21473. doi 10.3390/ molecules191221473
- Rammohan A., Reddy J.S., Sravya G., Rao C.N., Zyryanov G.V. // Environ. Chem. Lett. 2020. Vol. 18. N 2. P. 433. doi: 10.1007/s10311-019-00959-w
- Khan S.A., Asiri A.M., Al-Ghamdi N.S.M., Asad M., Zayed M.E.M., Elroby S.A.K., Aqlan F.M., Wani M.Y., Sharma K. // J. Mol. Struct. 2019. Vol. 1190. P. 77. doi: 10.1016/j.molstruc.2019.04.046
- Gouhar R.S., Ewies E.F., El-Shehry M.F., Shaheen M.N.E, Ibrahim E.-M.M.E. // J. Heterocycl. Chem. 2018. Vol. 55. P. 2368. doi: 10.1002/jhet.3301
- Samshuddin S., Narayana B., Sarojini B.K., Khan M.T.H., Yathirajan H.S., Raj C.G.D., Raghavendra R. // Med. Chem. Res. 2011. Vol. 21. N 8. P. 2012. doi: 10.1007/s00044-011-9735-9
- Гимадиева А.Р., Чернышенко Ю.Н., Мустафин А.Г., Абдрахманов И.Б. // Баш. xим. ж. 2007. Т. 14. № 3. C. 78.
- Lagoja I.M. // Chem. Biodivers. 2007. Vol. 2. N 1. P. 1. doi: 10.1002/cbdv.200490173
- Мартинкевич Д.С., Чернявская Е.Ф., Тарасевич В.А. // Весцi НАН Беларусi. Cер. хим. навук. 2021. Т. 57. № 4. С. 431. doi: 10.29235/1561-8331-2021-57-4-431-437
- Rani A., Anand A., Kumar K., Kumar V. // Exp. Opin. Drug Discov. 2019. Vol. 14. N 3. P. 249. doi: 10.1080/17460441.2019.1573812
- Mehmood R., Sadiq A., Alsantali R.I., Mughal E.U., Alsharif M.A., Naeem N., Javid A., Al-Rooqi M.M., Chaudhry G.-S., Ahmed S.A. // ACS Omega. 2022. Vol. 7. N 4. P. 3775. doi: 10.1021/acsomega.1c06694
- Чиряпкин А.С. // Juvenis Scientia. 2022. T. 8. № 5. С. 16. doi: 10.32415/jscientia_2022_8_5_16-30
- Varghese B., Al-Busafi S.N., Suliman F.O., Al-Kindy S.M.Z. // RSC Adv. 2017. Vol. 7. P. 46999. doi: 10.1039/C7RA08939B
- Ahmed M.H., El-Hashash M.A., Marzouk M.I., El-Naggar A.M. // J. Heterocycl. Chem. 2019. Vol. 56. P. 114. doi: 10.1002/jhet.3380
- Patil S.B. // Int. J Pharm. Sci. Res. 2018. Vol. 9. N 1. P. 44. doi: 10.13040/IJPSR.0975-8232.9(1).44-52
- Zhang B., Guo T., Li Z., Kühn F.E., Lei M., Zhao Z.K., Xiao J., Zhang J., Xu D., Zhang T., Li C. // Nat. Commun. 2022. Vol. 13. Art. no. 3365. doi: 10.1038/s41467-022-30815-5
- Achelle S., Rodríguez-Lopez J., Larbani M., Plaza-Pedroche R., Robin-le Guen F. // Molecules. 2019. Vol. 24. P. 1742. doi: 10.3390/molecules24091742
- Агарков А.С., Кожихов А.А., Нефедов А.А., Овсянников А.С., Исламов Д.Р., Соловьева С.Е., Антипин И.С. // Докл. РАН. Науки о материалах. 2022. T. 505. C. 50. doi: 10.31857/S2686953522700078; Agarkov A.S., Kozhikhov A.A., Nefedov A.A., Ovsyannikov A.S., Islamov D.R., Solovyova S.E., Antipin I.S. // Doklady Chem. 2022. Vol. 505. P. 177. doi: 10.1134/S0012500822700070
- Арутюнян А.А., Сумбатян А.С., Амбарцумян А.А., Паносян Г.А., Григорян А.С., Степанян Г.М., Мурадян Р.Е. // ЖОрХ. 2023. Т. 59. № 9. С. 1179. doi: 10.31857/S0514749223090082; Harutyunyan A.A., Sumbatyan A.S., Ambartsumyan A.A., Panosyan G.A., Grigoryan A.S., Stepanyan G.M., Muradyan R.E. // Russ. J. Org. Chem. 2023. Vol. 59. N 9. P. 1511. doi: 10.1134/S1070428023090087
- Lakowicz J.R. Principles of Fluorescence Spectroscopy. New York: Springer, 2006. P. 954. doi: 10.1007/978-0-387-46312-4
- Brouwer A.M. // Pure Appl. Chem. 2011. Vol. 83. N 12. P. 2213. doi: 10.1351/PAC-REP-10-09-31
- Hambardzumyan A.A., Hovsepyan A.S., Hayrapetyan H.L., Chailyan S.G. // Int. J. Pept. Res. Ther. 2021. Vol. 27. P. 1597. doi: 10.1007/s10989-021-10194-z
- Trott O., Olson A.J. // J. Comput. Chem. 2010. Vol. 31. P. 455. doi: 10.1002/jcc.21334
- Gao Y., Yan L., Huang Y., Liu F., Zhao Y., Cao L., Wang T., Sun Q., Ming Z., Zhang L., Ge J., Zheng L., Zhang Y., Wang H., Zhu Y., Zhu C., Hu T., Hua T., Zhang B., Yang X., Li J., Yang H., Liu Z., Xu W., Guddat L.W., Wang Q., Lou Zh., Rao Z. // Science. 2020. Vol. 368. N 6492. P. 779. doi: 10.1126/science.abb7498
- Kirsch K., Zeke A., Tőke O., Sok P., Sethi A., Sebő A., Kumar G.S., Egri P., Póti Á.L., Gooley P., Peti W., Bento I., Alexa A., Remény A. // Nat. Commun. 2020. Vol. 11. Art. no. 5769. doi: 10.1038/s41467-020-19582-3
- Kawakita Y., Seto M., Ohashi T., Tamura T., Yusa T., Miki H., Iwata H., Kamiguchi H., Tanaka T., Sogabe S., Ohta Y., Ishikawa T. // Bioorg. Med. Chem. 2013. Vol. 21. P. 2250. doi: 10.1016/j.bmc.2013.02.014
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