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Synthesis and characterization of novel 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) and dihydro-alkylthio-benzyloxopyrimidine (S-DABO) analogs containing a benzo[d]thiazol moiety

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Abstract

A series of novel dihydro-alkylthio-benzyloxopyrimidine (S-DABO) and 1-[(2-hydroxyethoxy) methyl]-6-(phenylthio)thymine (HEPT) analogs bearing a (benzo[d]thiazol-2-yl)methyl moiety at the C6 position of the pyrimidine core have been synthesized. 5-Allyl-6-{(benzo[d]thiazol-2-yl)methyl}-2-thiouracil and 5-allyl-6-{(benzo-[d]thiazol-2-yl)methyl}uracil were alkylated to give, respectively, S2- and N1- ethoxymethyl and -methylthiomethyl uracil derivatives. 5-Allyl-6-[(benzo[d]thiazol-2-yl)methyl]-2-thiouracil was also alkylated by S2 with methyl bromoacetate and hydrolyzed to the corresponding acid.

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References

  1. Petersen, L., Hansen, T., Khalifa, N., Pedersen, E., and Nielsen, C., Monatsh. Chem., 2002, vol. 133, p. 1031.

    Article  CAS  Google Scholar 

  2. Khalifa, N., J. Biol. Pharm. Sci., 2004, vol. 2(1), p. 57.

    Google Scholar 

  3. Khalifa, N., Al-Omar, M., Amr, A., and Abd-Elmoez, S., J. Pure Appl. Microbiol., 2014, vol. 8(2), p. 505.

    Google Scholar 

  4. Naglah, A., Khalifa, N., Al-Omar, M., Awad, H., and Amr, A., Dig. J. Nanomater. Bios., 2014, vol. 9(1), p. 433.

    Google Scholar 

  5. Abdel Salam, O., Khalifa, N., Said, S., and Amr, A., Res. Chem. Intermed., 2014, vol. 40, p. 1147.

    Article  CAS  Google Scholar 

  6. Khalifa, N., Pedersen, E., Nielsen, C., and Al-Omar, M., Russ. J. Bioorg. Chem., 2014, vol. 40(5), p. 579.

    Article  CAS  Google Scholar 

  7. Khalifa, N., and Al-Omar, M., Int. J. Mol. Sci., 2014, vol. 15, p. 20723.

    Article  Google Scholar 

  8. Eweas, A., Khalifa, N., Ismail, N., Al-Omar, M., and Soliman, A., Med. Chem. Res., 2014, vol. 23, p. 76.

    Article  CAS  Google Scholar 

  9. Haiba, M., Al-Abdullah, E., Edrees, M., and Khalifa, N., Drug Res., 2015, vol. 65, p. 9.

    CAS  Google Scholar 

  10. Ismail, M., Khalifa, N., Fahmy, H., Nossier, E., and Abdulla, M., J. Heterocycl. Chem., 2014, vol. 51, p. 450.

    Article  CAS  Google Scholar 

  11. Khalifa, N., Al-Omar, M., Amr, A., Baiuomy, A., and Abdel-Rahman, R., Russ. J. Bioorg. Chem., 2015, vol. 41(2), p. 192.

    Article  CAS  Google Scholar 

  12. Khalifa, N., Al-Omar, M., Amr, A., and Haiba, M., Int. J. Biol. Macromol., 2013, vol. 54, p. 51.

    Article  CAS  Google Scholar 

  13. Mao, C., Sudeck, E.A., Venkatachalam, T.K., and Uckun, F.M., Biochem. Pharmacol., 2000, vol. 6, p. 1251.

    Article  Google Scholar 

  14. Robert, C., Wang, D., Julian, T., and William, L., J. Am. Chem. Soc., 2000, vol. 122, p. 12898.

    Article  Google Scholar 

  15. Nawrozkij, M., Rotili, D., Tarantino, D., Botta, G., Eremiychuk, A., Musmuca, I., Ragno, R., Samuele, A., Zanoli, S., Armand, U., Clotet-Codina, I., Novakov, I., Orlinson, B., Maga, G., Est, J., and Artico, M., J. Med. Chem., 2008, vol. 51, p. 4641.

    Article  CAS  Google Scholar 

  16. Tanaka, H., Tajashia, H., Ubasawa, M., Sekiya, K., Inouye, N., Baba, M., Shigeta, S., Wallker, R., De Clercq, E., and Miyasaka, T., J. Med. Chem., 1995, vol. 38, p. 2860.

    Article  CAS  Google Scholar 

  17. Hopkins, A., Ren, J., Tanaka, H., Baba, M., Okamato, M., Stuart, D., and Stammers, D., J. Med. Chem., 1999, vol. 42, p. 4500.

    Article  CAS  Google Scholar 

  18. Vig, R., Mao, C., Venkatachalam, T., Tuel-Ahlgren, L., and Uckun, F., Bioorg. Med. Chem. Lett., 1998, vol. 8, p. 1461.

    Article  CAS  Google Scholar 

  19. He, Y., Chen, F., Yu, X., Wang, Y., De Clercq, E., Balzarini, J., and Pannecouque, C., Bioorg. Chem., 2004, vol. 32, p. 536.

    Article  CAS  Google Scholar 

  20. Hannick, S.M, and Kishi, Y.J., J. Org. Chem., 1983, vol. 48, p. 3833.

    Article  CAS  Google Scholar 

  21. Vorbrüggen, H., Krolikiewicz, K., and Bennua, B., Chem. Ber., 1981, vol. 114, p. 1234.

    Article  Google Scholar 

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Correspondence to N. M. Khalifa.

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Khalifa, N.M., Nossier, E.S., Al-Omar, M.A. et al. Synthesis and characterization of novel 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) and dihydro-alkylthio-benzyloxopyrimidine (S-DABO) analogs containing a benzo[d]thiazol moiety. Russ J Gen Chem 86, 400–405 (2016). https://doi.org/10.1134/S107036321602033X

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  • DOI: https://doi.org/10.1134/S107036321602033X

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