CORROLES AS AROMATIC ANALOGS OF CORRINOIDS AND VITAMIN B12: SYNTHESIS, STRUCTURAL FEATURES AND MACROCYCLE PROPERTIES, PERSPECTIVES OF MATERIAL CHEMISTRY ON CORROLE BASIS
Abstract and keywords
Abstract (English):
The review deals with literature and own experimental data for synthesis, structural features, spectral, acid-basic and coordinating properties of aromatic macroheterocycles – corroles. Perspectives of practical application of these compounds are considered briefly. Relationship between corrole properties and its geometrical and π-electronic structure is demonstrated. It is shown that corroles have number of features and unique characteristics in despite of insignificant change of structure compared to the most studied class of macroheterocyclic compounds – porphyrins.

Keywords:
tetrapyrrolic macroheterocyclic compounds; porphyrins; corroles; synthesis; spectral characteristics; acid-basic and coordinating properties; metallocomplexes; catalysis; photodynamic therapy
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References

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175. Aviv I., Gross Z. Iron corroles and porphyrins as very efficient and highly selective catalysts for the reactions of α-diazo esters with amines. Synlett. 2006. V. 6. P. 951–953.

176. Aviv I., Gross Z. Iron porphyrins catalyse the synthesis of non-protected amino acid esters from ammonia and diazoacetates. Chem. Commun. 2006. P. 4477–4479.

177. Simkhovich L., Gross Z. Iron(IV) corroles are potent catalysts for aziridination of olefins by chloramine-T. Tetrahedron Lett. 2001. V. 42. P. 8089–8092.

178. Mairena M.A., Diaz-Requejo M.M., Belderrain T.R., Nicasio M.C., Trofimenko S., Perez P.J. Copper-homoscorpionate complexes as very active catalysts for the olefin aziridination reaction. Organometallics. 2004. V. 23. P. 253–256.

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191. Walker D., Chappel S., Mahammed A., Weaver J.J., Brunschwig B.S., Winkler J.R., Gray H.B., Zaban A., Gross Z. Corrole-sensitized TiO2 solar cells. J. Porph. Phthaloc. 2006. V. 10. P. 1259-1262.

192. Wiedau-Pazos M., Goto J.J., Rabizadeh S., Gralla E.B., Roe J.A., Lee M.K., Valentine J.S., Bredsen D.E. Altered reactivity of superoxide dismutase in familial amyotrophic lateral sclerosis. Science. 1996. V. 271. P. 515-518.

193. Yondim M.B.H., Mandel S., Amit T., Bar-Am O., Kupershmidt L., Gross Z., Mahammed A., Saltsman I., Okun Z. Corroles for neuroprotection and neurorescue. US. Pat. 20110098262, 28.04.2011.

194. Teo R.D., Hwang J.Y., Termini J., Gross Z., Gray H.B. Fighting cancer with corroles. Chem. Rev. 2016. V. 117 (4). R. 2711-2729.

195. Hwang J.Y., Lubow J., Chu D. A mechanistic study of tumor-targeted corrole toxicity. Mol. Pharm. 2011. V. 8. P. 2233-2243.

196. Agostinis P., Berg K., Cengel K.A. Photodynamic therapy of cancer: an update. Cancer J. Clin. 2011. V. 61. P. 250-281.

197. Lim P., Mahammed A., Okun Z., Saltsman I., Gross Z., Gray H.B., Termini J. Differential cytostatic and cytotoxic action of metallocorroles against human cancer cells: potential platforms for anticancer drug development. Chem. Res. Toxicol. 2012. V. 25. P. 400−409.

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199. Aviezer D., Cotton S., David M., Segev A., Khaselev N., Galili N., Gross Z., Yayon A. Porphyrin analogues as novel antagonists of fibroblast growth factor and vascular endothelial growth factor receptor binding that inhibit endothelial cell proliferation, tumor progression, and metastasis. Cancer Res. 2000. V. 60. P. 2973–2980.

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204. Pohl J., Saltsman I., Mahammed A., Gross Z., Röder B. Inhibition of green algae growth by corrole-based photosensitizers. J. Appl. Microbiol. 2014. V. 118. P. 305-312.

205. Hwang J.Y., Wachsmann-Hogiu S., Ramanujan V.K. Multimodal wide-field two-photon excitation imaging: characterization of the technique for in vivo applications. Biomed. Opt. Express. 2011. V. 2. N. 2. P. 356- 364.

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