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Ukr. Bioorg. Acta 2021, Vol. 16, N2, 23-28.

Synthesis and NMR spectroscopy investigations of functionalized spiropyranochromenediones and their spirothiadiazole derivatives

Viktoria S. Moskvina1,2*, Olexander V. Turov1, Tetyana V. Shokol1, Volodymyr P. Khilya1

1 Taras Shevchenko National University of Kyiv, Volodymyrska St., 64, Kyiv
2 V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine,
1 Murmanska St., Kyiv, 02094, Ukraine

tel.: +380-44-239-3342; e-mail: v.moskvina@gmail.com

This investigation focuses on the synthesis of spiropyranoneoflavones and the modification of obtained compounds at the exocyclic oxygen atom. Kabbe cyclization of 6-acetyl-7-hydroxy-8-methyl-4-phenyl-2H-chromene-2-one with cyclohexanone or cyclopentanone in the presence of pyrrolidine provided 10-methyl-4-phenyl-2H-spiro[cyclohexane(cyclopentane)-1,8-pyrano[3,2-g]chromene]-2,6(7H)-diones. Their new functionalized derivatives with thiosemicarbazide residues were synthesized. Acetylation of obtained thiosemicarbazones with acetic anhydride proceeded via cyclization of thiosemicarbazide fragment into 1,3,4-thiadiazole ring to give corresponding N-[3'-acetyl-10-methyl-8-oxo-6-phenyl-3'H,8H-dispiro[cyclohexane-1,2-pyrano[3,2-g]chromene-4,2'-[1,3,4]thiadiazol]-5'-yl]acetamide and N-[3'-acetyl-10-methyl-8-oxo-6-phenyl-3'H,8H-dispiro[cyclopentane-1,2-pyrano[3,2-g]chromene-4,2'-[1,3,4]thiadiazol]-5'-yl]acetamide. The structure of the obtained compounds was confirmed by NMR spectroscopy.

spiro compounds; neoflavones; spiropyranochromenediones; NMR spectroscopy; heteronuclear correlation.

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          1. Garazd, M. M.; Garazd, Ya. L.; Khilya, V. P. Neoflavones. 1. Natural Distribution and Spectral and Biological Properties. Chem. Nat. Compd. 2003, 39, 54-121.
          2. Itoigawa, M.; Ito, C.; Tan, H. T. W.; Kuchide, M.; Tokuda, H.; Nishino, H.; Furukawa, H. Cancer chemopreventive agents, 4-phenylcoumarins from Calophyllum inophyllum. Cancer Lett. 2001, 169, 15-19.
          3. Guilet, D.; Helesbeux, J. J.; Seraphin, D.; Sevenet, T.; Richomme, P.; Bruneton, J. Novel Cytotoxic 4-Phenylfuranocoumarins from Calophyllum dispar. J. Nat. Prod. 2001, 64, 563-568.
          4. Lee, J. M.; Tseng, T. H.; Lee, Y. J.; Synthesis An Efficient Synthesis of Neoflavonoid Antioxidants Based on Montmorillonite K-10. Catalysis. 2001, 2247-2254.
          5. Shah, S., Vyas, R., Mehta, R. H. Synthesis and antibacterial activities of some Mannich bases from coumarinderivatives. J. Indian Chem. Soc. 1991, 68, 411-412.
          6. Desai, P., Mehta, R. Synthesis of some Mannich bases from coumarin derivatives and their antibacterial activities. Indian J. Heterocycl. Chem. 1996, 5, 319-320,
          7. Finnegan, R. A.; Morris, M.P. Djerassi C. Naturally Occurring Oxygen Heterocyclics. X. 4-Phenyl-5,7-dihydroxy-6-isovaleryl-8-isopentenylcoumarin. J. Org. Chem. 1961, 26, 1180-1184.
          8. Moskvina, V. S.; Garazd, Ya. L.; Garazd, M. M.; Turov, A. V.; Khilya, V.P. Synthesis and structure of 4-arylspirodihydro-pyranochromen-2-one derivatives. Chem. Heterocycl. Compd. 2007, 43, 421-429.
          9. Moskvina, V. S.; Turov, O. V.; Khilya, V. P.; Garazd, M. M.; Groth, U. M. Synthesis and NMR spectroscopy investigations of functionalized 8,8,10-trimethyl-4-phenyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromene-2,6-diones and their spirothiadiazole derivatives. Monatsh. Chem. 2008, 139, 1391-1396.
          10. Moskvina, V. S.; Khilya, V. P. Synthesis of pyrano[2,3-f]chromen-2,8-diones and pyrano[3,2-g]chromen-2,8-diones based on o-hydroxyformyl(acyl)neoflavonoids. Chem. Nat. Compd. 2008, 44, 16-23.
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