A New Iodovinyl Derivative of Methyl Pyropheophorbide d Obtained via Takai Olefination Reaction
DOI: 10.6060/mhc224669b
Аннотация
Modification of chlorin derivatives, which leads to extention of the conjugation chain along the y axis, is the most important direction in the field of natural tetrapyrrole compounds. Our scientific group is interested in the search and development of universal methods which allowing us to introduce substituents of various nature and at the same time, extend the conjugation chain along the y axis of the macrocycle. A new alternative way for functionalization of C32-position of formyl group methyl pyrophrophorbide d by introducing of iodine has been developed. We have proposed an one-step synthesis of methyl 3-(2-iodovinyl)pyropheophorbide d that including Takai reaction between methyl pyropheophorbide d, iodoform and CrCl2. This functionalized derivative can be useful for further synthesis derivatives with π-extending system by Pd-catalysed cross-coupling reaction.
Литература
Koifman O.I., Ageeva T.A., Beletskaya I.P., Averin A.D., Yakushev A.A., Tomilova L.G., Dubinina T.V., Tsivadze A.Yu., Gorbunova Yu.G., Martynov A.G., Konarev D.V., Khasanov S.S., Lyubovskaya R.N., Lomova T.N., Korolev V.V., Zenkevich E.I., Blaudeck T., von Borczyskowski Ch., Zahn D.R.T., Mironov A.F., Bragina N.A., Ezhov A.V., Zhdanova K.A., Stuzhin P.A., Pakhomov G.L., Rusakova N.V., Semenishyn N.N., Smola S.S., Parfenyuk V.I., Vashurin A.S., Makarov S.V., Dereven’kov I.A., Mamardashvili N.Zh., Kurtikyan T.S., Martirosyan G.G., Burmistrov V.А., Aleksandriiskii V.V., Novikov I.V., Pritmov D.A., Grin M.A., Suvorov N.V., Tsigankov A.A., Fedorov A.Yu., Kuzmina N.S., Nyuchev A.V., Otvagin V.F., Kustov A.V., Belykh D.V., Berezin D.B., Solovieva A.B., Timashev P.S., Milaeva E.R., Gracheva Yu.A., Dodokhova M.A., Safronenko A.V., Shpakovsky D.B., Syrbu S.A., Gubarev Yu.A., Kiselev A.N., Koifman M.O., Lebedeva N.Sh., Yurina E.S. Macroheterocycles 2020, 13, 311-467. https://doi.org/10.6060/mhc200814k
Meng S., Xu Z., Hong G., Zhao L., Zhao Z., Guo J., Ji H., Liu T. Eur. J. Med. Chem. 2015, 92, 35-48. https://doi.org/10.1016/j.ejmech.2014.12.029
Nakano T., Liu Y., Wang X.-F., Tamiaki H. J. Photochem. Photobiol. A 2022, 424, 113633. https://doi.org/10.1016/j.jphotochem.2021.113633
Koifman O.I.,Ageeva T.A. Russ. J. Org. Chem. 2022, 58, 443-479. https://doi.org/10.1134/S1070428022040017
Quaranta M., Borisov S.M., Klimant I. Bioanalyt. Rev. 2012, 4, 115-157. https://doi.org/10.1007/s12566-012-0032-y
Papkovsky D.B., Dmitriev R.I. Chem. Soc. Rev. 2013, 42, 8700-8732. https://doi.org/10.1039/c3cs60131e
Dmitriev R.I., Papkovsky D.B. Cell. Mol. Life Sci. 2012, 69, 2025-2039. https://doi.org/10.1007/s00018-011-0914-0
Worlinsky J.L., Halepas S., Ghandehari M., Khalil G., Brückner C. Analyst 2015, 140, 190-196. https://doi.org/10.1039/C4AN01462F
Liu E., Ghandehari M., Brückner C., Khalil G., Worlinsky J., Jin W., Sidelev A., Hyland M.A. Cement Concrete Res. 2017, 95, 232-239. https://doi.org/10.1016/j.cemconres.2017.02.001
Borchert N.B., Ponomarev G.V., Kerry J.P., Papkovsky D.B. Analyt. Chem. 2011, 83, 18-22. https://doi.org/10.1021/ac1025754
Cao L., Guo X., Wang L., Wang S., Li Y., Zhao W. New J. Chem. 2017, 41, 14279-14287. https://doi.org/10.1039/C7NJ03279J
Belyaev E.S., Shkirdova A.O., Kozhemyakin G.L., Tyurin V.S., Emets V.V., Grinberg V.A., Cheshkov D.A., Ponomarev G.V., Tafeenko V.A., Radchenko A.S., Kostyukov A.A., Egorov A.E., Kuzmin V.A., Zamilatskov I.A. Dyes Pigm. 2021, 191, 109354. https://doi.org/10.1016/j.dyepig.2021.109354
Wang K., Osuka A., Song J. ACS Cent. Sci. 2020, 6, 12, 2159-2178. https://doi.org/10.1021/acscentsci.0c01300
Aratani N., Osuka A. Org. Lett. 2001, 3, 26, 4213-4216. https://doi.org/10.1021/ol0168770
Yin B., Kim T., Zhou M., Huang W., Kim D., Song J. Org. Lett. 2017, 19, 10, 2654-2657. https://doi.org/10.1021/acs.orglett.7b00988
Sergeeva N.N., Scala A., Bakar M.A., O'Riordan G., O'Brien J., Grassi G., Senge M.O. J. Org. Chem. 2009, 74, 7140-7147. https://doi.org/10.1021/jo901535c
Tremblay-Morin J.-P., Ali H., van Lier J.E. Tetrahedron Lett. 2006, 47, 3043-3046. https://doi.org/10.1016/j.tetlet.2006.03.018
Handbook of Porphyrin Science: With Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medicine (Kadish K.M., Smith K.M., Guilard R., Eds.), 2012, Vols. 21-25, 2228 p.
Lonin I.S., Kuzovlev A.S., Belyaev E.S., Ponomarev G.V., Koifman O.I., Tsivadze A.Yu. J. Porphyrins Phthalocyanines 2014, 18, 123-128. https://doi.org/10.1142/S108842461350123X
Belyaev E.S., Kozhemyakin G.L., Tyurin V.S., Frolova V.V., Lonin I.S., Ponomarev G.V., Buryak A.K., Zamilatskov I.A. Org. Biomol. Chem. 2022, 20, 1926-1932. https://doi.org/10.1039/D1OB02005F
Geddis S.M., Hagerman C.E., Galloway W.R.J.D., Sore H.F., Goodman J.M., Spring D.R. Beilstein J. Org. Chem. 2017, 13, 323-328. https://doi.org/10.3762/bjoc.13.35
Takai K., Nitta K., Utimoto K. J. Am. Chem. Soc. 1986, 108, 7408-7410. https://doi.org/10.1021/ja00283a046
Tamiaki H., Fukai K., Shimazu H., Shoji S. Photochem. Photobiol. 2014, 90, 121-128. https://doi.org/10.1111/php.12173
Kenner G.W., McCombie S.W., Smith K.M. J. Chem. Soc., Perkin Trans. 1 1973, 2517-2523. https://doi.org/10.1039/p19730002517
Pennington F.C., Strain H.H., Svec W.A., Kat J.J. J. Am. Chem. Soc. 1964, 86, 1418-1426. https://doi.org/10.1021/ja01061a030
Johnson D.G., Svec W. A., Wasielewski R. Israel J. Chem. 1988, 28, 193-203. https://doi.org/10.1002/ijch.198800030
Shaughnessy K.H. Molecules 2015, 20, 9419-9454. https://doi.org/10.3390/molecules20059419
Miyaura N., Suzuki A. Chem. Rev. 1995, 95, 2457-2483. https://doi.org/10.1021/cr00039a007
Galushko A.S., Prima D.O., Burykina J.V., Ananikov V.P. Inorg. Chem. Front. 2021, 8, 620-635. https://doi.org/10.1039/D0QI01133A
Vikse K., Naka T., McIndoe J.S., Besora M., Maseras F. ChemCatChem 2013, 5, 3604-3609. https://doi.org/10.1002/cctc.201300723
