Synthesis of anticancer compounds

Arthur Armenovich Harutyunyan, D.Sc. (Chemistry) ORСID: org/0000-0003-0641-5453

Phone: (+37410) 288-323

STCOPC, Institute of Fine Organic Chemistry, Laboratory No. 2 “Synthesis of Antitumor Compounds”

e-mail: harutyunyan.arthur@yahoo.com

The laboratory’s research focus is the synthesis of new derivatives of five- and six-membered nitrogen-containing heterocycles: imidazoles, 1,2,4-triazoles, 1,3,4-thiadiazoles, pyrazoles, pyrimidines, quinazolines, quinolines, 1,2,4-triazines, benzimidazoles, benzo[b]thiophenes and condensed bi-, tri- and tetracyclic heterocycles and framework compounds based on them. Synthesis of hybrid compounds built on the principle of combining various heterocycles directly linked to each other or linked via a linker. Synthesis of derivatives of the natural antibiotic chloramphenicol, synthesis of nucleosides, targeted chemical modification of nucleic acid metabolism antimetabolites in the series of substituted pyrimidines. Together with the laboratories of the Center and a number of scientific institutions of the NAS RA (Scientific and Production Center “Armbiotechnology”, G. Bunyatyan Institute of Biochemistry, Institute of Molecular Biology, Yerevan State University, Slavic University), docking and in-depth biological and physicochemical studies of synthesized compounds are carried out.

Brief history of Laboratory No. 2 of the IFOC “Synthesis of antitumor compounds”.

After the transformation of the Yerevan Scientific Research Chemical-Pharmaceutical Laboratory of the Ministry of Health of the Armenian SSR into the Institute of Fine Organic Chemistry of the Academy of Sciences of the Armenian SSR in 1955 on the initiative of A.L. Mndzhoyan, in 1959 it included sector of heterocyclic compounds No. 2 was founded, which after 1974 received the name Laboratory No. 2 ‘Synthesis of antitumor compounds‘.

The first scientific director of the newly formed sector from 1959 to 1974 was Doctor of Chemical Sciences Harutyun Asaturovich Haroyan. During this time, the sector conducted a systematic study of the chloromethylation reaction, on the basis of which anticancer drugs with alkylating action were synthesized, and pioneering research began on the synthesis of new biologically active derivatives of 1,2,4-triazole, imidazole, benzofuran, pyrimidine and their condensed systems. From 1974 to 2014, the scientific director of the laboratory was Doctor of Chemical Sciences Rafik Gegamovich Melik-Ohanjanyan, under whose leadership the work on the synthesis of derivatives of pyrimidines and condensed pyrimidines (imidazo-, furo- and thienopyrimidines), pyrido[2,3-d]pyrimidines, pyrimidine nucleosides, analogs of the antitumor antibiotic sparsomycin continued. During this period, a significant contribution to the research of Laboratory No. 2 of the IFOC was made by the laboratory staff, who served in it practically from its very foundation, Doctor of Chemical Sciences Melkon Arpiarovich Iradyan (research in the field of imidazole and development of the anticancer drug Imidazen), Ph.D. Mari Hrutyunovna Kaldrikyan (development of the antiulcer drug Dimecoumarone), Ph.D. Taguhi Rubenovna Ovsepyan (research in the field of 1,2,4-triazole, 1,3,4-oxa- and thiadiazole, complex compounds, development of the drug Gumetox) and other employees. From 2014 to 2019, the scientific management of the laboratory was carried out by Ph.D. Taguhi Rubenovna Ovsepyan, during which the traditional research areas of the laboratory were continued. From 2019 to the present, the scientific director of Laboratory No. 2 of IFOC is Artur Armenovich Harutyunyan.

The laboratory employs 10 specialists in their field, including 1 D.Sc. (Chem.), 2 Ph.D. (Chem.).

Currently, in the laboratory, taking into account modern trends in pharmaceutical and bioorganic chemistry, research continues on the synthesis of new derivatives of five- and six-membered nitrogen-containing heterocycles, with the inclusion of new azaheterocycles and polycyclic azaheterocycles in the research topics for the laboratory, studies have begun on derivatives of the antibiotic chloramphenicol and derivatives of spiro[chromene-4,3′-indoline] and spiro(indoline-3,4′-pyrano[3,2-h]quinoline).

The generalized structure of laboratory research is shown schematically below:

Since 2020, the laboratory has published more than 65 printed works and received 2 RA patents

Since 2020, the laboratory No. 2 of the IFOC has…”

published works” or “printed works

  1. Dilanyan S.V., Hovsepyan T.R., Nersesyan L.E., Aharonyan A.S., Danielyan I.S., Minasyan N.S., Harutyunyan А.А. // J. Gen. Chem.2020, No 5, v. 90, p.787–793. doi.org/10.1134/S1070363220050047.
  2. Poghosyan S.A., Poghosyan M.V., Harutyunyan A.A. // J. Org. Chem. 2020, v. 56, No 2, p. 213-217. doi: 10.1134/S1070428020020062
  3. Harutyunyan A.A., Panosyan G.A., Safaryan M.S., Harutyunyan G.K., Gukasyan G.T., Danagulyan G.G.. Russ. J. Org. Chem., 2020, v. 56, No 2, p. 269-275. doi 1134/S1070428020020153
  4. Isakhanyan A.U., Hakobyan N.Z., Grigoryan A.S., Navoyan K.G., Gasparyan G.V., Mkhitaryan R.P., Panosyan G.A., Harutyunyan A.A. // Russ J Gen Chem, 2022, 92, No. 11, pp 2516-2520. doi: 10.1134/S1070363222110391.
  5. Harutyunyan A.A., Safaryan M.S., Dilanyan S.V. Panosyan H. A., Danagulyan G. G. // Russ J Org Chem. 59, №2, p. 243–251. https://doi.org/10.1134/S1070428023020045.
  6. Harutyunyan, A.A., Sumbatyan, A.S., Hambardzumyan, A.A. Panosyan H. A., Grigoryan A. S., Stepanyan H. M., Muradyan R. E..// J. Org. Chem. 2023, 59, №9 1511–1522. doi.org/10.1134/S1070428023090087
  7. Isakhanyan A.U., Hakobyan N.Z., Hovasyan Z.A., Nersesyan L.E., Aharonyan A.S., Danielyan I.S., Panosyan Н.A., Harutyunyan A.A. // Russ. J. Gen. Chem., 2023, Vol. 93, No. 4, pp. 795–799. doi.org/10.1134/S107036322­3040047
  8. Harutyunyan A., Israelyan S. G., Safaryan M. S., Sumbatyan A. S., Nersesyan L. E., Aharonyan A. S., Danielyan I. S., Muradyan R. E., Sargsyan A. S., Hambar­dzum­yan A. A., Panosyan H. A. //. Russ. J. Org. Chem., 2024, Vol. 60, No. 10, pp. 1909–1920. doi: 10.1134/S1070428024100051
  9. Isakhanyan A. , Hakobyan N. Z., Muradyan R. E., Tumajyan A. E., Panosyan H. A., and Harutyunyan A. A. // Russ. J. Org. Chem., 2024, Vol. 60, No. 3, pp. 539–542. doi: 10.1134/S1070428024030230.
  10. Paronikyan R. G., Grigoryan A. S., Barkhudaryants I. M., Arshakyan L. M., Harutyunyan A. A. // Bioactive Compounds in Health and Disease 2024; 7(5): 274-288. org/10.31989/bchd.v7i5.1357
  11. А. А. Арутюнян, С. Г. Исраелян, М. Р. Акобян, М. С. Сафарян, Р. А. Мадоян, А. Г. Сукиасян, К. А. Геворкян, А. Д. Арутюнян, А. С. Саргсян, А. А. Амбарцумян, А. А. Карапетян, А. А. Мнацаканян, Г. А. Паносян, М. Ю. Дангян, С. П. Гаспарян. // Russ. J. Gen. Chem. 2024; том 94, № 11, p. 2809 – 2823. doi: 1134/S107036322411001X
  12. Арутюнян А.А., Акобян М.Р., Саргсян А.С., Aмбарцумян А.А., Степанян Г.М.,

Григорян А.С., Паносян Г.А. // Russ. J. Org. Chem., 2025, т.61, No 1, с.1-15. doi:

10.1134/S1070428024601894

  1. Hakobyan N. Z., Safaryan M. S., Grigoryan A. S., Alaverdyan Zh. R., Paronikyan R. G.,

Mirzoyan L. S., Gasparyan H. V., Panosyan Н. A., Harutyunyan A. A.// Russ. J. Gen. Chem.,

2025, Vol. 95, No. 4, pp. 927-934. doi: 10.1134/S107036322560021

  1. Исаханян А. У., Овасян З. А., Мадоян Р. A, Сукиасян A. Г., Чаилян С. Г, Григорян А.

С, Гаспарян Г. В., Арутюнян А. А. // Биоорг. химия, 2025, Т. 51, № 1, С. 137. doi:

10.31857/S0132342325010126