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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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

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Supplementary files

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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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