Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2016. V. 59. N 10. P. 36-40


This work describes synthesis, methods of purification and physical-chemical charac-teristics of ABBB-type macroheterocyclic compound, which contains fragment of 5-amino-2-dodecyl-3-imino-1,2,4-thiadiazoline. This compound has similar to tetraazabacteriochlorin structure and it can be used as potentially sensitizer for photodynamic therapy of cancer. Moreover, 3,5-diamino-1,2,4-thiadiazole is standard antihypoxant and its biological proper-ties can occur in desired macroheterocyclic product. Parent compound, namely 5-amino-2-dodecyl-3-imino-1,2,4-thiadiazoline, was synthesized by alkylation of 3,5-diamino-1,2,4-thiadiazole by 1-bromododecane. Macroheterocyclic compound of ABBB-type has been pre-pared by condensation 1,3-diiminoizoindoline (fragment B) and 5-amino-2-dodecyl-3-imino-1,2,4-thiadiazoline (fragment A) in phenol. Purification of obtained compound was carry out by method of column chromatography on silica gel using eluting mixture CH2Cl2:MeOH:C6H14. Both compounds were characterized by mass-spectrometry, 1H NMR, UV-vis, IR spectroscopy. It was shown, that bathochromic shift of absorbtion maximum from 480 to 555 nm and emergence of new inflection at 692 and 721 nm are observed in UV-vis spectra of macroheterocyclic compound in acid medium, that confirms protonation of ob-tained compound. Acid-based behavior of this compound will be described in the next work.

Key words: macroheterocyclic compound, tetraazabacteriochlorin structure, alkylation, 5-amino-2-dodecyl-3-imino-1,2,4-thiadiazoline

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