Examples



mdbootstrap.com



 
Статья
2022

Key structures in the synthesis of steroid antitumor agents. Methods for upbuilding the 17β-pregnane side chain of 3-methoxy-19-norpregna-1,3,5(10)-trien-20-ones with and without an additional 16α,17α-carbocycle


M. O. TserfasM. O. Tserfas, Yu. V. KuznetsovYu. V. Kuznetsov, I. V. ZavarzinI. V. Zavarzin
Российский химический вестник
https://doi.org/10.1007/s11172-022-3593-0
Abstract / Full Text

Methods for extending the side chain of 20-oxopregnanes were summarized. The possibilities of alkylation of 3-methoxy-19-norpregna-1,3,5(10)-trien-20-one and its 16α,17α-methano and -butano derivatives with alkyl halides in the presence of lithium diisopropylamide were studied. The Claisen—Schmidt condensation of these steroids with aromatic aldehydes resulted in a series of the corresponding 21-benzylidenesteroids. Carrying out the Claisen—Schmidt condensation in an aprotic solvent in the presence of lithium diisopropylamide yielded, in addition to the target 21-benzylidenesteroids, the corresponding 21-benzoyl derivatives — steroidal 1,3-diketones.

Author information
  • N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian FederationM. O. Tserfas, Yu. V. Kuznetsov, V. V. Knyazev, I. S. Levina & I. V. Zavarzin
References
  1. R. L. Siegel, K. D. Miller, A. Jemal, CAA Cancer J. Clin., 2020, 70, 7; DOI: https://doi.org/10.3322/caac.21590.
  2. F. Lumachi, D. A. Santeufemia, S. M. M. Basso, World J. Biol. Chem., 2015, 6, 231; DOI: https://doi.org/10.4331/wjbc.v6.i3.231.
  3. K. Dahlman-Wright, V. Cavailles, S. A. Fuqua, V. C. Jordan, J. A. Katzenellenbogen, K. S. Korach, A. Maggi, M. Muramatsu, M. G. Parker, J. A. Gustafsson, Pharmacol. Rev., 2006, 58, 773; DOI: 10.1124%2Fpr.58.4.8.
  4. B. J. Deroo, K. S. Korach, J. Clin. Invest., 2006, 116, 561; DOI: https://doi.org/10.1172/JCI27987.
  5. K. A. Burns, K. S. Korach, Arch. Toxicol., 2012, 86, 1491; DOI: https://doi.org/10.1007/s00204-012-0868-5.
  6. D. P. McDonnell, S. E. Wardell, Cur. Opin. Pharmacol., 2010, 10, 620; DOI: https://doi.org/10.1016/j.coph.2010.09.007.
  7. J. A. R. Salvador, J. F. S. Carvalho, M. A. C. Neves, S. M. Silvestre, A. J. Leitao, M. M. C. Silva, M. L. S. Melo, Nat. Prod. Rep., 2013, 30, 324; DOI: https://doi.org/10.1039/C2NP20082A.
  8. A. J. Begam S. Jubie, M. J. Nanjan, Bioorg. Chem., 2017, 71, 257; DOI: https://doi.org/10.1016/j.bioorg.2017.02.011.
  9. D. P. McDonnell, S. E. Wardell, J. D. Norris, J. Med. Chem., 2015, 58, 4883; DOI: https://doi.org/10.1021/acs.jmedchem.5b00760.
  10. H. K. Patel, T. Bihani, Pharm. Therap., 2018, 186, 1; DOI: https://doi.org/10.1016/j.pharmthera.2017.12.012.
  11. T. Traboulsi, M. El Ezzy, J. L. Gleason, S. Mader, J. Mol. Endocrinol., 2017, 58, R15; DOI: https://doi.org/10.1530/JME-16-0024.
  12. N. Kumar, H. K. Gulat, A. Sharma, Sh. Heer, A. K. Jassal, L. Arora, S. Kaur, A. Singh, K. Bhagat, A. Kaur, H. Singh, J. V. Singh, P. Mohinder, S. Bedi, Molec. Divers., 2021, 25, 603; DOI: https://doi.org/10.1007/s11030-020-10133-y.
  13. Yu. V. Kuznetsov, I. S. Levina, A. M. Scherbakov, O. E. Andreeva, I. V. Fedyushkina, A. S. Dmitrenok, A. S. Shashkov, I. V. Zavarzin, Eur. J. Med. Chem., 2018, 143, 670; DOI: https://doi.org/10.1016/j.ejmech.2017.11.042.
  14. Yu. V. Kuznetsov, I. S. Levina, A. M. Scherbakov, O. E. Andreeva, A. S. Dmitrenok, O. R. Malyshev, I. V. Zavarzin, Steroids, 2018, 137, 1; DOI: https://doi.org/10.1016/j.steroids.2018.07.007.
  15. A. M. Scherbakov, I. S. Levina, Y. Kuznetsov, M. Tserfas, I. Zavarzin, Ann. Oncol., 2020, 31, Suppl. 1, 58; DOI: https://doi.org/10.1016/j.annonc.2020.01.042.
  16. M. O. Tserfas, Yu. V. Kuznetsov, I. S. Levina, I. V. Zavarzin, Russ. Chem. Bull., 2019, 68, 2350; DOI: https://doi.org/10.1007/s11172-019-2710-1.
  17. I. Kitagawa, M. Kobayashi, Chem. Pharm. Bull., 1978, 26, 1864.
  18. J. R. Hanson, P. B. Hitchcock, J. A. R. Salvador, J. Chem. Res. (S), 2003, 9, 556; DOI: https://doi.org/10.3184/030823403322597298.
  19. J. Cairns, R. T. Logan, G. McGarry, R. G. Roy, D. F. M. Stevenson, G. F. Woods, J. Chem. Soc., Perkin Trans. 1, 1981, 2306; DOI: https://doi.org/10.1039/P19810002306.
  20. W. Dong, H. Yang, W. Yang, W. Zhao, Org. Lett., 2020, 22, 1265; DOI: https://doi.org/10.1021/acs.orglett.9b04508.
  21. I. Cornella, J. P. Sestelo, A. Mouriño, L. A. Sarandeses, J. Org. Chem., 2002, 67, 4707; DOI: https://doi.org/10.1021/jo020022z.
  22. T. Chen, H. Yang, Y. Yang, G. Dong, D. Xing, ACS Catal., 2020, 10, 4238; DOI: https://doi.org/10.1021/acscatal.0c00019.
  23. M. S. Kwon, N. Kim, S. H. Seo, I. S. Park, R. K. Cheedrala, J. Park, Angew. Chem., Int. Ed. Engl., 2005, 44, 6913; DOI: https://doi.org/10.1002/anie.200502422.
  24. R. Mamidala, S. Samser, N. Sharma, U. Lourderaj, K. Venkatasubbaiah, Organometallics, 2017, 36, 3343; DOI: https://doi.org/10.1021/acs.organomet.7b00478.
  25. J. Das, M. Vellakkaran, D. Banerjee, J. Org. Chem., 2019, 84, 769; DOI: https://doi.org/10.1021/acs.joc.8b02609.
  26. M. Kaur, N. U. D. Reshi, K. Patra, A. Bhattacherya, S. Kunnikuruvan, J. K. Bera, Chem. Eur. J., 2021, 27, 10737; DOI: https://doi.org/10.1002/chem.202101360.
  27. G. Pawar, S. M. Ghouse, S. Kar, S. M. Chelli, S. R. Dannarm, J. Gour, R. Sonti, S. Nanduri, Chem. Asian J., 2022, 17, e202200041; DOI: https://doi.org/10.1002/asia.202200041.
  28. S. A. Runikhina, O. I. Afanasyev, K. Biriukov, D. S. Perekalin, M. Klussmann, D. Chusov, Chem. Eur. J., 2019, 25, 16225; DOI: https://doi.org/10.1002/chem.201904605.
  29. B. Li, C. Li, J. Org. Chem., 2014, 79, 2242; DOI: https://doi.org/10.1021/jo500213b.
  30. R. E. Marker, E. L. Wittle, J. Am. Chem. Soc., 1939, 61, 1329; DOI: https://doi.org/10.1021/ja01875a005.
  31. C.-S. Jiang, X.-J. Guo, J.-X. Gong, T.-T. Zhu, H.-Y. Zhang, Y.-W. Guo, Bioorg. Med. Chem. Lett., 2012, 22, 2226; DOI: https://doi.org/10.1016/j.bmcl.2012.01.103.
  32. M. B. Tufail, M. A. Javed, M. Ikram, M. H. Mahnashi, B. A. Alyami, Y. S. Alqahtani, A. Sadiq, U. Rashid, Steroids, 2021, 168, 108801; DOI: https://doi.org/10.1016/j.steroids.2021.108801.
  33. M. I. Choudhary, M. S. Alam, A. Rahman, S. Yousuf, Y.-C. Wu, A.-S. Lin, F. Shaheen, Steroids, 2011, 76, 1554; DOI: https://doi.org/10.1016/j.steroids.2011.09.006.
  34. X. Cai, S. Zhao, D. Cai, J. Zheng, Z. Zhu, D. Wei, Z. Zheng, H. Zhu, Y. Chen, Steroids, 2019, 146, 70; DOI: https://doi.org/10.1016/j.steroids.2019.03.012.
  35. X. Cai, F. Sha, C. Zhao, Z. Zheng, S. Zhao, Z. Zhu, H. Zhu, J. Chen, Y. Chen, Steroids, 2021, 171, 108830; DOI: https://doi.org/10.1016/j.steroids.2021.108830.
  36. N.-J. Fan, J.-J. Tang, He Li, X.-J. Li, B. Luo, J.-M. Gao, Eur. J. Med. Chem., 2013, 69, 182; DOI: https://doi.org/10.1016/j.ejmech.2013.08.016.
  37. N.-J. Fan, J.-J. Tang, Y.-F. Li, Y.-B. Bai, X.-M. Zhao, Heterocycles, 2019, 98, 822; DOI: https://doi.org/10.3987/COM-19-14075.
  38. A. M. Scherbakov, I. V. Zavarzin, S. K. Vorontsova, A. Hajra, O. E. Andreeva, A. V. Yadykov, I. S. Levina, Y. A. Volkova, V. Z. Shirinian, Steroids, 2018, 138, 91; DOI: https://doi.org/10.1016/j.steroids.2018.06.013.
  39. B. Yu, X.-N. Sun, X.-J. Shi, P.-P. Qi, Y.-C. Zheng, D.-Q. Yu, H.-M. Liu, Steroids, 2015, 102, 92; DOI: https://doi.org/10.1016/j.steroids.2015.08.003.
  40. M. V. Dansey, M. C. del Fueyo, A. S. Veleiro, P. H. Di Chenna, Steroids, 2017, 121, 40; DOI: https://doi.org/10.1016/j.steroids.2017.03.003.
  41. X. Zhang, N. Xu, K.-B. Li, S. Lin, F.-Z. Lu, F.-S. Du, F.-M. Li, Tetrahedron Lett., 2006, 47, 2623; DOI: https://doi.org/10.1016/j.tetlet.2006.02.019.