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Synthesis, Structure, and Analgesic Properties of Phosphorylated Dihydro-1,4-Benzodiazepin-2-Ones*

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Condensation of 3-hydroxy-5-aryl-1.2-dihydro-3H-1.4-benzodiazepin-2-ones with diphenylchlorophosphine was found to produce 3- or 5-diphenylphosphine oxides with high analgesic activity; ED50 values were (0.08 ± 0.02) – (0.97 ± 0.27) mg/kg.

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References

  1. S. A. Andronati, L. N. Yakubovskaya, A. S. Yavorskii, et al., USSR Patent No. 1828645.

  2. K. S. Andronati, E. A. Kostenko, T. L. Karaseva, and S. A. Andronati, Khim.-Farm. Zh., 36, No. 7, 16 – 18 (2002); Pharm. Chem. J., 36(7), 356 – 359 (2002).

  3. S. Andronati, E. Semenishyna, V. Pavlovsky, et al., Eur. J. Med. Chem., 45(4), 1346 – 1351 (2010).

    Article  CAS  PubMed  Google Scholar 

  4. T. A. Voronina, Vestnik Psikhiatr. Psikhofarmakoter., 18(2), 13 – 24 (2010).

    Google Scholar 

  5. O. Palaoglu and I. H. Ayhan, Pharmacol. Biochem. Behav., 25, 215 – 217 (1986).

    Article  CAS  PubMed  Google Scholar 

  6. H. U. Zeilhofer, R. Witschiand, and K. J. Hössl, Mol. Med., 87, 465 (2009).

    Article  CAS  Google Scholar 

  7. H. U. Zeilhofer, D. Benke, and G. E. Yevenes, Annu. Rev. Pharmacol. Toxicol., 52, 111 – 133 (2012).

    Article  CAS  PubMed  Google Scholar 

  8. E. K. Dziadulewicz, M. C. Brown, A. R. Dunstan, et al., Bioorg. Med. Chem. Let., 9, 463 – 468 (1999).

    Article  CAS  Google Scholar 

  9. V. I. Pavlovsky, O. V. Tsymbalyuk, V. S. Martynyuk, et al., Neurophysiology, 45(5/6), 427 – 432 (2013).

    Article  CAS  Google Scholar 

  10. S. A. Andronati, T. A. Kabanova, V. I. Pavlovskii, et al., Odesskii Med. Zh., 123(1), 17 – 21 (2011).

    Google Scholar 

  11. V. I. Pavlovskii, T. A. Kabanova, E. A. Semenishina, et al., Vestnik ONU, 18(3), 28 – 37 (2013).

    Google Scholar 

  12. J. H. Sellstedt, J. Org. Chem., 40(10), 1508 (1975).

    Article  CAS  Google Scholar 

  13. E. Lattmann, P. Lattmann, Y. Boonprakob, et al., Arzneimittel-Forschung, 59(2), 61 (2009).

    CAS  PubMed  Google Scholar 

  14. G. M. Sheldrick, SADABS, v. 2.03, Bruker / Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin (2003).

  15. G. M. Sheldrick, Acta Cryst., A64, 112 – 122 (2008).

    Article  Google Scholar 

  16. O. V. Stefanov, Preclinical Drug Research. Methodological Recommendations [in Ukrainian], Avicena, Kiev (2001), pp. 312 – 313.

  17. V. B. Prozorovskii, Psikhofarmakol. Biol. Narkol., 7(3 – 4), 2090 – 2120 (2007).

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Correspondence to V. I. Pavlovskii.

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*For preliminary communication see: Yu. G. Gololobov, I. Yu. Krasnova, S. V. Barabanov, V. N. Khrustalev, S. A. Andronati, and V. I. Pavlovsky, Tetrahedron Let., 55, 4879 (2014); DOI:10.1016/j.tetlet.2014.07.010.

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 50, No. 4, pp. 22 – 26, April, 2016.

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Pavlovskii, V.I., Gololobov, Y.G., Andronati, S.A. et al. Synthesis, Structure, and Analgesic Properties of Phosphorylated Dihydro-1,4-Benzodiazepin-2-Ones*. Pharm Chem J 50, 229–233 (2016). https://doi.org/10.1007/s11094-016-1428-8

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  • DOI: https://doi.org/10.1007/s11094-016-1428-8

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