- PII
- S30345596S0044460X25070031-1
- DOI
- 10.7868/S3034559625070031
- Publication type
- Article
- Status
- Published
- Authors
- Volume/ Edition
- Volume 95 / Issue number 7-8
- Pages
- 256-268
- Abstract
- Simple and effective methods were proposed for the synthesis of previously undescribed substituted pyrimido[4',5':4,5]pyrrolo[1,2-]pyridazine-2,4(1,3)-diones and their 8,9-dihydro derivatives. Structure of the prepared compounds was studied using IR, NMR, UV spectroscopy, quantum chemical calculations and single crystal X-ray diffraction analysis.
- Keywords
- пиримидопирроло[1,2-]пиридазин-2,4(1,3)-дионы енаминокетон спектры поглощения квантово-химические расчеты рентгеноструктурный анализ
- Date of publication
- 05.07.2025
- Year of publication
- 2025
- Number of purchasers
- 0
- Views
- 54
References
- 1. Popovici L., Amarandi R.-M., Mangalagiu I.I., Mangalagiu V., Danac R. // J. Enz. Inhibit. Med. Chem. 2018. Vol. 34. P. 230. doi 10.1080/14756366.2018.1550085
- 2. Saito T., Obitsu T., Kohno H., Sugimoto I., Matsushita T., Nishiyama T., Takaoka Y. // Bioorg. Med. Chem. 2012. Vol. 20. P.1122. doi 10.1016/j.bmc.2011.11.015
- 3. Ostby O.B., Dalhus B., Gundersen L.-L., Rise F., Bast A., Haenen G.R.M.M. // Eur. J. Org. Chem. 2000. Vol. 22. P. 3763. doi 10.1002/1099-0690(200011)2000:223.0.CO;2-С
- 4. Østby O.B., Gundersen L.-L., Rise F., Antonsen Ø., Fosnes K., Larsen V., Bast A., Custers I., Haenen G.R.M.M. // Arch. Pharm. 2001. Vol. 334. P. 21. doi 10.1002/1521-4184(200101)334:13.0.CO;2-W
- 5. Ohtani M., Fuji M., Fukui Y., Adachi M. WO Pat. 059999 (1999).
- 6. Salvati M.E, Illig C.R., Wilson K.J., Chen J., Meegalla S.K., Wall M.J. US Pat. 7030112B2 (2006).
- 7. Fu J.-M. US Pat. 7074791 (2006).
- 8. Hynes J., Jr., Wu H., Kempson J., Duan J.J.-W., Lu Z., Jiang B., Stachura S., Tokarski J.S., Sack J.S., Khan J.A., Lippy J.S., Zhang R.F., Pitt S., Shen G., Gillooly K., McIntyre K., Carter P.H., Barrish J.C., Nadler S.G., Salter-Cid L.M., Fura A., Schieven G.L., Pitts W.J., Wrobleski S.T. // Bioorg. Med. Chem. Lett. 2017. Vol. 27. P. 3101. doi 10.1016/j.bmcl.2017.05.043
- 9. Kempson J., Ovalle D., Guo J., Wrobleski S.T., Lin S., Spergel S.H., Duan J.J.-W., Jiang B., Lu Z., Das J., Yang B.V., Hynes J., Jr., Wu H., Tokarski J., Sack J.S., Khan J., Schieven G., Blatt Y., Chaudhry C., Salter-Cid L.M., Fura A., Barrish J.C., Carter P.H., Pitts W.J. // Bioorg. Med. Chem. Lett. 2017. Vol. 27. P. 4622. doi 10.1016/j.bmcl.2017.09.023
- 10. Duan J.J.-W., Lu Z., Jiang B., Yang B.V., Doweyko L.M., Nirschl D.S., Haque L.E., Lin S., Brown G., Hynes J., Jr., Tokarski J.S., Sack J.S., Khan J., Lippy J.S., Zhang R.F., Pitt S., Shen G., Pitts W.J., Carter P.H., Barrish J.C., Nadler S.G., Salter-Cid L.M., McKinnon M., Fura A., Schieven G.L., Wrobleski S.T. // Bioorg. Med. Chem. Lett. 2014. Vol. 24. P. 5721. doi 10.1016/j.bmcl.2014.10.061
- 11. Cheng Y., Ma B., Wudl F. // J. Mater. Chem. 1999. Vol. 9. P. 2183. doi 10.1039/A903025E
- 12. Mitsumori T., Bednikov M., Sedó J., Wudl F. // Chem. Mater. 2003. Vol. 15. P. 3759. doi 10.1021/cm0340532
- 13. Mitsumori T., Craig I.M., Martini I.B., Schwartz B.J., Wudl F. // Macromolecules. 2005. Vol. 38. P. 4698. doi 10.1021/ma048091y
- 14. Swamy K.M.K., Park M.S., Han S.J., Kim S.K., Kim J.H., Lee C., Bang H., Kim Y., Kim S.-J., Yoon J. // Tetrahedron. 2005. Vol. 61. N 43. P. 10227. doi 10.1016/j.tet.2005.08.038
- 15. Mangalagiu I.I., Zbancioc G.N. // Synlett. 2006. Vol. 5. P. 0804. doi 10.1055/s-2006-932459
- 16. Ткаченко Ю.Н., Цупак Е.Б., Пожарский А.Ф. // ХГС. 1999. № 3. C. 375; Tkachenko Yu.N., Tsupak E.B., Pozharskii A.F. // Chem. Heterocycl. Compd. 1999. Vol. 35. N 3. P. 328. doi 10.1007/BF02259364
- 17. Ткаченко Ю.Н., Попов Л.Д., Пожарский А.Ф., Бородкин С.А., Левченков С.И. // ЖОрХ. 2017. Т. 53. Вып. 10. С. 1536
- 18. Tkachenko Yu.N., Popov L.D., Pozharskii A.F., Borodkin S.A., Levchenkov S.I. // Russ. J. Org. Chem. 2017. Vol. 53. N 10. P. 1564. doi 10.1134/S1070428017100128
- 19. Somei M., Matsubara M., Natsume M. // Chem. Pharm. Bull. 1975. Vol. 23. N 11. P. 2891. doi 10.1248/cpb.23.2891
- 20. Allen F.H., Kennard O., Watson D.G., Brammer L., Guy Orpen A., Taylor R. // J. Chem Soc. Perkin Trans. II. 1987. P. 1. doi 10.1039/P298700000S1
- 21. Steiner T. // Crystallogr. Rev. 1996. Vol. 6. N 1. P. 1. doi 10.1080/08893119608035394
- 22. Janiak C. // Dalton Trans. 2000. N 21. P. 3885. doi 10.1039/b003010o
- 23. Somei M., Natsume M. // Tetrahedron Lett. 1974. Vol. 15. N 41. P. 3605. doi.org/10.1016/S0040-4039(01)91979-3
- 24. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Jr., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., Pople J.A. Gaussian 03, Revision D.01. Gaussian, Inc., Wallingford CT, 2004.
- 25. Zhurko G.A. Chemcraft ver. 1.5 trial, build 266. www.chemcraftprog.com/description.html
- 26. CAChe 4.4. CAChe WorkSystem, USA, CAChe Group, Fujitsu Systems Business of America. http://www.cachesoftware.com
- 27. SMART and SAINT, Release 5.0, Area Detector control and Integration Software, Bruker AXS, Analytical X-Ray Instruments, Madison, Wisconsin, USA, 1998.
- 28. Sheldrick G.M. SADABS: A Program for Exploiting the Redundancy of Area-detector X-Ray Data. University of Göttingen, Göttingen, Germany, 1999.
- 29. Sheldrick G.M. // Acta Crystallogr. (A). 2008. Vol. 64. N 1. P. 112. doi 10.1107/S0108767307043930
- 30. Spek A.L. // J. Appl. Crystallogr. 2003. Vol. 36. P. 7. doi 10.1107/S0021889802022112