3RD INTERNATIONAL CONGRESS ON TECHNOLOGY - ENGINEERING & SCIENCE - Kuala Lumpur - Malaysia (2017-02-09)

Synthesis And Configuration Of N-methyl-1-[phenyl] Fullerene-c60[1,9c] Pyrrolidine Based On Aminoaldehydes

Interaction of C60 with N-methyl glycine and 4-amino-substituted aromatic aldehydes (4-piperidilbenzaldegid, 4-morfolinobenzaldegid, 4-cytisinilbenzaldehyde) under the reaction conditions gave the corresponding Prato fullerenpirrolidiny that are potentially biologically active substances. By using 1H and 13C NMR and mass spectrometry identified the structure of the synthesized compounds. Since its discovery and isolation, the fullerenes have attracted attention of an increasing number of scientists. Due to its fascinating physical and chemical properties, C60 and its derivatives have been extensively applied in such areas as supramolecular materials, nano sciences [1, 2] and biological systems [3]. One of the most commonly used method for C60functionalization is the 1,3-dipolar cycloaddition of azamethine ylides with the C60[6,6] bond [4], which leads to selective formation, and as a rule, to free-machining fulleropyrrolidine derivatives. In this work we have described the results of joining three new molecule aldehydes derived from piperidine, morpholine and alkaloid cytisine to C60. So, we tried to expand the list of new bioactive compounds derived as a result of the reaction of Prato. The most effective method in generating of azomethine ylides is based on decarboxylation immonie salts obtained by condensation of α-amino acids with aldehydes (Prato reaction). Very often Prato reaction is used to produce fullerene derivatives with potential biological activity. Continuing the investigation in this direction, we've synthesized new fulleropirrolidines (2 а-с) by the interaction of [60]fullerene with N-methylglycine (sarcosine) and 4-amino-substituted aromatic aldehydes (1 а-с) in refluxing toluene for 4 hours as follows: Unreacted starting materials and reaction products 2 a-c after the reaction were separated by column chromatography on SiO2, eluting with toluene, then with pyridine. At the beginning of the process the initial and unreacted C60 and then fulleropirrolidines targets 2 a-c with 88% 2a, 62 % 2b, 38% 2c were released. All adducts 2 a-c are stable compounds. Thus, based on the aromatic aldehyde (4-piperidilbenzaldehyde, 4-morfolinobenzaldehyde, 4-cytisinilbenzaldehyde) and [60]fullerene in conditions of Prato reaction new fulleropir-rolidines were synthesized, which are interesting as potential bioactive compounds. Keywords: [60]fullerene, 4-aminobenzaldehyde, Prato reaction, fulleropirrolidine References: [1] Kadish K.M., Ruoff, R.S.: Chemistry, Physics and Technology. Wiley, NewYork (2000). [2] Hirsch A., Brettreich M.: Chemistry and Reactions. Wiley-VCH, Weinheim (2005). [3] Bosi S., Da Ros Т., Spalluto G., Balzarini J., Prato M.: Synthesis and Anti-HIV Properties of New Water-Soluble Bis-functionalized С60 fullerene Derivatives. Bioorganic & Medicinal Chemistry Letters, 13, 4437- 4440 (2003) [4] Mashino T., Nishikawa D., Takanashi K., Usui N., Yamori T., Seki M., Endo T., Mochizuki M.: Antibacterial and antiproliferative activity of cationic fullerene derivatives. Bioorg. Med. Chem. Lett., 13, 4395-4397 (2003).
Keywords: Fullerene, 4-aminobenzaldehyde, Prato reaction, fulleropirrolidine
S.D. Fazylov, O.A. Nurkenov, A.E. Arinova, T.M. Seilkhanov, Z.B. Satpaeva, A. Zh. Issayev