The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH2Cl, and MeSCH2Cl in the K2CO3–DMF, NaOMe–MeOH, and KOH–EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-{[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one.
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References
K. Danel, E. B. Pedersen, and C. Nielsen, J. Med. Chem., 41, 191 (1998).
O. S. Pedersen, L. Petersen, and M. Brandt, Monatsh. Chem., 130, 1499 (1999).
M. B. Navrotskii, Thesis for Cand. Pharm. Sci. [in Russian], Pyatigorsk (2002).
O. G. Sim, Thesis for Cand. Pharm. Sci. [in Russian], (2006).
A. Mai, M. Artico, G. Sbardella, S. Massa, A. G. Loi, E. Tramontano, P. Scano, and P. La Colla, J. Med. Chem., 38, 3258 (1995).
M. B. Nawrozkij, Khim. Farm. Zh., 37, No. 9, 22 (2003).
Yu. A. Pokonova, Halogen Sulfides. Methods of Production, Properties, Application of Thioether Halides [in Russian], Izd. LGU, Leningrad (1977).
E. A. Sudbeck, C. Mao, R. Vig, T. K. Venkatachalam, L. Tuel-Ahlgren, and F. M. Uckun, Antimicrob. Agents Chemother., 42, 3225 (1998).
G. Sbardella, A. Mai, M. Artico, S. Massa, T. Marceddu, L. Vargiu, M. E. Maron-giu, and P. La Colla, Med. Chem. Res., 10, 30 (2000).
K. Danel, C. Nielsen and E. B. Pedersen, Acta Chem. Scand., 51, 426 (1997).
N. R. El-Brollosy, P. T. Jorgensen, B. Dahan, A. M. Boel, E. B. Pedersen, and C. Nielsen, J. Med. Chem., 45, 5721 (2002).
A. Mai, M. Artico, G. Sbardella, S. Massa, E. Novellino, G. Greco, A. G. Loi, E. Tramontano, M. E. Marongiu, and P. La Colla, J. Med. Chem., 42, 619 (1999).
H. Bohme, Ber., 69, 1612 (1936).
L. A. Walter, L. H. Goodson, and R. J. Fosbinder, J. Am. Chem. Soc., 67, 655 (1945).
A. Mai, G. Sbardella, M. Artico, R. Ragno, S. Massa, E. Novellino, G. Greco, A. Lavecchia, C. Musiu, M. La Colla, C. Murgioni, P. La Colla, and R. Loddo, J. Med. Chem., 44, 2544 (2001).
M. B. Nawrozkij, D. Rotili, D. Tarantino, G. Botta, A. S. Eremiychuk, I. Musmuca, R. Ragno, A. Samuele, S. Zanoli, M. Armand-Ugon, I. Clotet-Codina, I. A. Novakov, B. S. Orlinson, G. Maga, J. A. Este, M. Artico, and A. Mai, J. Med. Chem., 51, 4641 (2008).
L. Titze and T. Eicher, Preparative Organic Chemistry: Reactions and Syntheses in Practical Organic Chemistry and Scientific Research Laboratory [Russian translation], Mir, Moscow (1999).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 248–254, February, 2010.
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Novakov, I.A., Orlinson, B.S., Nawrozkij, M.B. et al. The specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides. Chem Heterocycl Comp 46, 200–205 (2010). https://doi.org/10.1007/s10593-010-0492-3
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DOI: https://doi.org/10.1007/s10593-010-0492-3