1Bogza, SL
1L.M. Litvinenko Institute of Physical Organic and Coal Chemistry, NAS of Ukraine, Kyiv
Nauka innov. 2015, 11(6):85-93
https://doi.org/10.15407/scin11.06.085
Section: The World of Innovations
Language: Russian
Abstract: 

Review of the investigations in the field of heterocyclic chemistry and medicinal chemistry in the Department of Biologically Active Compounds of L.M. Litvinenko Institute of Physical Organic and Coal Chemistry of NAS of Ukraine is presented. The results of the search of new drugs on the base of β-carboline structures, its S- and O- isosteres, isoquinoline are shown

Keywords: carbolines, drug, isoquinoline, organic synthesis, tranquilizer onkolitik
References: 
1. Andronati S.A., Javorskij A.S., Chepelev V.M. i dr. Mehanizmy dejstvija anksioliticheskih, protivosudorozhnyh i snotvornyh sredstv. Kyiv: Nauk. dumka, 1988 [in Russian].
2. Dulenko V.I., Komissarov I.V., Dolzhenko A.T. i dr. β-Karboliny. Himija i nejrobiologija. Kyiv: Nauk. dumka, 1992 [in Russian].
3. Thornber C.W. Isosterism and molecular modification in drug design. Chemical Society Reviews. 1979, 8(4): 563-580.
http://dx.doi.org/10.1039/cs9790800563
4. Stradyn’ Ja.P. Novye imennye reakcii v himii getie rociklicheskih soedinenij. HGS. 1981, N 10: 1412 [in Russian].
5. Dorofeenko G.N., Dulenko L.V. Novyj metod pristrojki pirilievogo i piridinovogo ciklov k proizvodnym furana i indole. HGS. 1969, N 3: 417-421 [in Russian].
6. Dorofeenko G.N., Dulenko L.V., Semenov N.S. Soli 2-benzopirilija. Vzaimodejstvie s azotistymi osnovanijami. HGS. 1970, N 2: 245-249 [in Russian].
7. Komissarov I.V., Dulenko L.V., Dulenko V.I. Sintez i farmakologicheskie svojstva proizvodnyh garmana i garmina. Him.-farmac. zhurn. 1977, 11(5): 93-97 [in Russian].
8. Dulenko V.I., Semenov N.S., Nikoljukin Ju.A. i dr. Sintez kondensirovannyh proizvodnyh indolo2,3-s.pirilievyh solej i β-karbolinov. HGS. 1971, N 4: 568 [in Russian].
9. Komissarov I.V., Dulenko V.I., Dolzhenko A.T. i dr. Farmakologicheskie svojstva proizvodnyh garmina. Him. farmac. zhurn. 1985, 19(3): 172-176 [in Russian].
10. Dulenko V.I., Luk’janenko V.I., Kibal’nyj A.V. i dr. Sintez kondensirovannyh proizvodnyh indolo[2,3-c]pirilievyh solej i β-karbolinov. HGS. 1985, N 3: 363-366 [in Russian].
11. Komissarov I.V., Dulenko V.I., Dolzhenko A.T i dr. Sintez i farmakologicheskie svojstva 1-alkil-3,4-tetra metilen-beta-karbolinov. Him.-farmac. zhurn. 1989, 23(6): 674-678 [in Russian].
12. Tolkunov S.V. Kislotno-kataliticheskoe acetilirovanie N-metallil’nyh proizvodnyh laktamov i imidov. HGS. 1988, N 10: 1414-1419 [in Russian].
13. Bogza S.L., Nikoljukin Ju.A., Zubrickij M.Ju., Dulenko V.I. Sintez pirrolo[3,4-c]izohinolindionov i pirrolo[3,4-c]-β-karbolindiona. ZhOrH. 1993, 29(7): 1480-1484 [in Russian].
14. Bogza S.L., Kobrakov K.I., Dulenko V.I. Ciklodeza minirovanie N-azolil-formamidinov. Sintez poliazage terociklov so strukturnymi fragmentami izohinolina i indolo-[2,3-c]-piridina. HGS. 1997, N 1: 80-84 [in Russian].
15. Dulenko V.I., Tolkunov S.V., Alekseev N.N Sintez i reakcii solej benzoj.tieno[2,3-s]pirilija. HGS. 1981, N 10: 1351-1354 [in Russian].
16. Tolkunov S.V., Dulenko V.I. Sintez i reakcii solej benzofuro[2,3-s]pirilija. HGS. 1987, N 7: 889-893 [in Russian].
17. Tolkunov S.V., Alekseev N.N. Novye geterociklicheskie sistemy proizvodnye pirilija i piridinija na osnove tieno[3,2-b]tiofena. HGS. 1979, N 10: 1424 [in Russian].
18. Tolkunov S.V., Hizhan A.I., Simonova S.I i dr. Kondensirovannye piridinovye osnovanija. Sintez nekotoryh proizvodnyh benzo[b]furo[2,3-c]-, benzo[b]tieno[2,3-c]-i benzo[b]selenofeno[2,3-c]hinolinov. HGS. 1994, N 3: 321-326 [in Russian].
19. Tolkunov S.V., Kal’nickij M.N., Dulenko V.I. Jelektrofil’noe zameshhenie v benzo[b]tieno[2,3-c]piridinah. Nitrovanie. HGS. 1993, N 5: 706-709 [in Russian].
20. Tolkunov S.V., Kal’nickij M.N., Dulenko V.I. Jelektrofil’noe zameshhenie v benzo[b]tieno[2,3-c]piridinah. Acilirovanie. HGS. 1994, N 5: 701-705 [in Russian].
21. Tolkunov S.V., Kal’nickij M.N., Ljashhuk S.N., Dulenko V.I. Jelektrofil’noe zameshhenie v benzo[b]furo[2,3-c]piridinah. Nitrovanie, acilirovanie. HGS. 1995, N 5: 694-699 [in Russian].
22. Tolkunov S.V., Kal’nickij M.N., Ljashhuk S.N., Dulenko V.I. Kondensirovannye piridinovye osnovanija. Reakcii 1-okso-3,3,6-trimetil-1,2,3,4-tetragidrobenzo/b/furohinolinov s jelektrofil’nymi agentami. HGS. 1995, N 8: 1124–1130 [in Russian].
23. Dolzhenko A.T., Zin’kovskaja A.Ja., Komissarov I.V. Trankvilizirujushhaja aktivnost’ garmana i 3-metilgarmana. Him.-farmac. zhurn. 1982, 16(12): 1474-1476 [in Russian].
24. A.s. 803383 SSSR. V.I. Luk’janenko, Ju.A. Nikoljukin, A.V. Kibal’nyj i dr. Gidrohlorid 3,3,6-trimetil-1,2,3,4-tetragidroindolo2,3shinolina, obladajushhij antidepressantnoj aktivnost’ju [in Russian].
25. A.s.1160709 SSSR. A.V.Kibal’nyj, Ju.A.Nikoljukin, A.T. Dolzhenko i dr.Gidrohlorid 6-metil-1-okso-1,2,3,4-tetragidroindolo/2,3-s/hinolina [in Russian].
26. A.s. 753093 SSSR. V.I.Luk’janenko, I.V.Komissarov, T.F. Larina i dr. Gidrohlorid 1-metil-3, 4-( 2, 2-dimetil-4-oksotetragidro benzo)-indolo-(2,3-s)-piridina, projavljajushhij trakvilizirujushhuju aktivnost’; # 2754361/23-04 [in Russian].
27. Pat. RF 2064793 A61K31/44. Stressprotektivnoe sredstvo, obladajushhee antiamnesticheskim, antigipoksicheskim, protivotrevozhnym i protivoshokovym dejstviem. Komissarov I. V., Titievskij A. V., Abramec I. I., Du lenko V. I., Nikoljukin Ju. A., Kibal’nyj A. V., Groshevoj T. A., Suhovoj G. F. [in Russian].
28. Tadashi Nagatani, Tsuneyuki Yamamoto, Katsuyuki Takao, Shinji Hashimoto, Kenichi Kasahara, Taisuke Sugihara, Showa Ueki. Pharmacological profile of a potential anxiolytic: AP159, a new benzothieno-pyridine derivative. Psychopharmacology. 1991, 104(4): 432-438.
http://dx.doi.org/10.1007/BF02245645
29. A.s. 123580 SSSR. V.I.Dulenko, S.V.Tolkunov, I.V. Komissarov i dr. Gidrohloridy benzotiofeno (2, 3 )piridinov, obladajushhie nejtrolepticheskoj aktivnost’ju [in Russian].
30. Kobrakov K.I., Malienko A.A., Sujkov S.Yu. et al. The Improved One Pot Synthesis of 5-Unsubstituted Pyrazolo[5,4-c]Isoquinolines. J. Heterocyclic Chem. 2001, 38 (3): 523-525.
31. Kobrakov K.I., Malienko A.A., Perepichka I.F. et al. A versatile synthesis of pyrasolo[3,4-c] isoquinoline derivatives by reaction of 4-aryl-5-amino-pyrazoles with aryl/heteroaryl aldehydes: the effect of heterocycle on the reaction pathways. Org.Biomol.Chem. 2005, 3(5): 932-940.
http://dx.doi.org/10.1039/b417002d
32. Li R., Xue L., Zhu T. et al. Design and Synthesis of 5-Aryl-pyridone-carboxamides as Inhibitors of Anaplastic Lymphoma Kinase. J. of Medicinal Chemistry. 2006, 49(3): 1006-1015.
http://dx.doi.org/10.1021/jm050824x
33. Oncolytics. Drug Data Report, 2007. 29(7): P. 644. 
34. Pat. US 7872014 1/ 5605, 657. Anaplastic lymphoma kinase modulators and methods of use. Neel Kumar Anand, Charles M. Blazey, Owen Joseph Bowles, Joerg Bussenius, Simona Costanzo, Jeffry Kimo Curtis, Larisa Dubenko, Abigail R. Kennedy, Richard G. Khoury, Angie I. Kim, Jean-Claire L. Manalo, Csaba J. Peto, Kenneth D. Rice, Tsze H. Tsang.
35. Kondratov R.V., Komarov P.G., Becker Y. et al. Small molecules that dramatically alter multidrug resistance phenotype by modulating the substrate specificity of P–glycoprotein. PNAS. 2001, 98(24): 14078-14083.
http://dx.doi.org/10.1073/pnas.241314798
36. Gudkov A., Kondratov R. Compounds capable of modulating the activity of multidrug transporters and therapeutic use of the same. US 20030073611.
37. Nikoljukin Ju.A., Zubrickij M.Ju., Dulenko V.I. Sintez pirrolo[3,4-c]izohinolindionov i pirrolo[3,4-c]-β-karbolindiona. Zh. org. himii. 1993, 29(7): 1480-1484 [in Russian].
38. Zinchenko S.Yu., Efimenko R.A., Suikov S.Yu, K.I. Kobrakov. Acid cyclization of amino-substituted heterocycles. Synthesis of 1,3-dioxo-pyrrolo[3,4-c]- and thieno[3,4-c]isoquinolines and cinnolines. Chem. of Heterocyclic Compounds. 2009, 45(3): 365-369.
http://dx.doi.org/10.1007/s10593-009-0262-2
39. Zhong H. et al. Characterization and development of novel small-molecules inhibiting GSK3 and activating Wnt signaling. Molecular BioSystems, 2009. 5(11): p. 1356-1360
http://dx.doi.org/10.1039/b905752h
40. Teller S. et al. Pyrrolo[3,4-c]-β-carboline-diones as a novel class of inhibitors of the platelet-derived growth factor receptor kinase. European Journal of Medicinal Chemistry, 2000. 35(4): p. 413-427.
http://dx.doi.org/10.1016/S0223-5234(00)00140-9
41. Pat US 7696221 B2. Richard D. C., William F. F., Eugene J. T. Thienoisoquinoline-phenylsulfonamides and their use as ER-NFkappaB inhibitors. US7696221 B2, US200 60154875.
42. Wong, N.W.Y. and P. Forgione. A One-Pot Double C–H Activation Palladium Catalyzed Route to a Unique Class of Highly Functionalized Thienoisoquinolines. Organic Letters, 2012. 14(11): 2738-2741.
http://dx.doi.org/10.1021/ol3009655