Pyrazolines and pyrimidines based on (E)-1-(4-pentyloxyphenyl)-3-arylprop-2-en-1-ones. Synthesis, docking study and luminescent properties

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(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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作者简介

A. Isakhanyan

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

编辑信件的主要联系方式.
Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0002-1713-4908
亚美尼亚, Yerevan

Z. 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
亚美尼亚, Yerevan

G. Grigoryan

Yerevan State University

Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0002-0675-735X
亚美尼亚, Yerevan

R. Mkhitaryan

Yerevan State University

Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0009-0009-6277-2747
亚美尼亚, Yerevan

L. Gabrielyan

Yerevan State University

Email: anush.isakhanyan.51@mail.ru
ORCID iD: 0000-0002-9212-9682
亚美尼亚, Yerevan

G. 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
亚美尼亚, Yerevan

M. 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
亚美尼亚, Yerevan

A. 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
亚美尼亚, Yerevan

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
亚美尼亚, Yerevan

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
亚美尼亚, Yerevan

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2. Fig. 1. Fluorescence spectra of samples 2–6 (1–5) in DMF solutions (c = 2·10–6 mol/l, excitation slit width – 10 nm, emission slit width – 10 nm).

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3. Fig. 2. Fluorescence spectra of samples 7–11 (1–5) in DMF solutions (c = 2·10–6 mol/l, excitation slit width – 5 nm, emission slit width – 5 nm).

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4. Fig. 3. Fluorescence spectra of samples 12, 13 and 14 (1–3) in DMF solutions (с = 2·10–6 mol/L, excitation slit width – 5 nm, emission slit width – 5 nm).

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5. Fig. 4. Fluorescence spectra of samples 15 (1) and 16 (2) in DMF solutions (с = 2·10–6 mol/l, excitation slit width – 5 nm, emission slit width – 5 nm).

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6. Fig. 5. Modes of interaction of compound 13 with RdRp, EGFR, MAPK14 and MAOB receptors.

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7. Scheme 1. R = H (2, 7, 12), OCH3 (3, 8, 13), Br (4, 9, 14), NMe2 (5, 10, 15), 1,3-бензодиоксол-5-ил (6, 11, 16).

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