Synthesis of Hydroxy Derivatives of Chlorin e6

Olga I. Gushchina,^@ Milana Yu. Grishina, Ekaterina A. Larkina, Victoriya S. Lebedeva, and Andrey F. Mironov

Moscow Technological University (Institute of Fine Chemical Technologies), 119571 Moscow, Russia

^@Corresponding author E-mail: ms.gushchina@inbox.ru

DOI: 10.6060/mhc161072g

Macroheterocycles 2017 10(1) 81-83

There is a simple scheme of synthesis of new chlorin photosensitizers (PS) based on chlorin е₆ hydroxy derivatives. For the disclosure of exocycle of the initial compounds – pheophorbide a and its methyl ester we used aliphatic aminoalcohols with 2-6 carbon atoms in the alkyl chain. The reaction was carried out under mild conditions in chloroform/dichloromethane with heating up to 40 °С. The structure of all compounds obtained was confirmed by means of electronic, IR, ¹Н NMR spectroscopy and mass-spectrometry. The yields of compounds 2a-e and3b-e were 60–75 %. It is necessary to note that chlorin е₆ hydroxy derivatives 2a-e could be soluble in water using alkaline compounds as excipients (namely KOH, NaOH). This fact is important and valuable because many effective porphyrin and chlorin PS are insoluble in water systems and obtaining of chlorin е₆ is time-consuming and hard work. Thus, in this paper we propose a reliable scheme of synthesis of new chlorin’s photosensitizers which are promising agents for PDT.

References:

Click here to expand or collapse this section

1. Bacellar I.O.L., Tsubone T.M., Pavani C., Baptista M.S. Int. J. Mol. Sci. 2015, 16, 20523-20559.
https://doi.org/10.3390/ijms160920523

2. Grin M.A., Mironov A.F., Shtil A.A. Anti-Cancer Agents in Medicinal Chemistry 2008, 8, 683-697.
https://doi.org/10.2174/187152008785133128

3. Agostinis P., Berg K., Cengel K.A., Foster T.H., Golab J. et al. CA Cancer J Clin. 2011, 61, 250–281.
https://doi.org/10.3322/caac.20114

4. Ethirajan M., Chen Y.H., Joshi P., Pandey R.K. Chem. Soc. Rev. 2011, 40, 340–362.
https://doi.org/10.1039/B915149B

5. Brown S.B., Brown E.A., Walker I.J. Lancet Oncol. 2004, 5, 497–508.
https://doi.org/10.1016/S1470-2045(04)01529-3

6. Voon S.H., Kiew L.V., Lee H.B., Lim S.H., Noordin M.I., Chung L.Y. et al. Small 2014,10, 4993-5013.
http://dx.doi.org/10.1002/smll.201401416

7. Allison R.R., Sibata C.H. Photodiagnosis and Photodynamic Therapy 2010, 7, 61—75.
https://doi.org/10.1016/j.pdpdt.2010.02.001

8. Belykh D.V., Kopylov E.A., Gruzdev I.V., Kuchin A.V. Rus. J. Org. Chem. 2010, 46, 577–585.
https://doi.org/10.1134/S1070428010040238

9. Kuchin A.V., Ol'shevskaya V.A., Mal'shakova M.V., Belykh D.V., Petrovskii P.V., Ivanov O.G., Shtil' A.A., Kalinin V.N. Doklady Akademii Nauk 2006, 409, 493–496.

10. Dugin N.O., Zavialova M.G., Novikov R.A., Timofeev V.P., Misharin A.Yu., Ponomarev G.V. Macroheterocycles 2012, 5, 146-148.
https://doi.org/10.6060/mhc2012.120468p

11. Gushchina O.I., Larkina E.A., Nikolskaya T.A., Mironov A.F. Photochem. Photobiol. B. 2015, 153, 76-81.
https://doi.org/10.1016/j.jphotobiol.2015.09.007

12. Larkina E.A., Bui T.L. An', Tkachevskaya E.P., Mironov A.F. Vestnik MITHT 2008, 3, 106-108.

13. Belykh D.V., Malysheva M.V., Kuchin A.V. Patent RU 2304583, 2007.

14. Belykh D.V., Karmanova L.P., Spirikhin L.V., Kuchin A.V. Rus. J. Org. Chem. 2007, 43, 120–128.
https://doi.org/10.1134/S1070428007010174

15. Tarabukina I. S., Startseva O. M., Patov S. A., Belykh D. V. Macroheterocycles 2015, 8, 168-176.
https://doi.org/10.6060/mhc150456b

Attachment	Size
mhc161072g.pdf	877.31 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

References: