New synthesis of cycloalca[с]nicotinoamide and nitrile derivatives

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Somente assinantes

Resumo

Nitriles and amide of nicotinic acid were synthesized by Knoevenagel reactions, nucleophilic vinyl substitution (SNVin), and alkylation. The structure of (1-amino-5-phenyl-5,6,7,8-tetrahydrothieno[2,3- c ]isoquinolin-2-yl)(phenyl)methanone was studied by X-ray analysis.

Sobre autores

I. Dyachenko

Lugansk State Pedagogical University

V. Dyachenko

Lugansk State Pedagogical University

P. Dorovatovskii

National Research Center “Kurchatov Institute”

V. Khrustalev

Peoples’ Friendship University of Russia (RUDN University);Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

G. Abakarov

Dagestan State Technical University

V. Nenajdenko

Lomonosov Moscow State University

Email: nenajdenko@gmail.com

Bibliografia

  1. Шкляев Ю.В. Химия и компьютерное моделирование. Бутлеровские сообщ. 2002, 7, 21-33.
  2. Zhang L., Song X., Wang N., Zhao L., Feng Q., You X., Peng C., Gao T., Xiong M., He B., Gao C., Luo Y., Xu Y., Zhang Q., Yu L. RSC Adv. 2015, 5, 25967-25978. doi: 10.1039/c5ra02365c
  3. Issac Y.A., Ali M.S., Erian A.W. Sci. Pharm. 2000, 68, 389-401. doi: 10.3797/scipharm.aut-00-36
  4. Kamal A.M., Radwan S.M., Zaki R.M. Eur. J. Med. Chem. 2011, 46, 567-578. doi: 10.1016/j.ejmech.2010.11.036
  5. Alman E.L., Painter H.I., Samra J., Carrasquilla M., Llinas M. Antimicrob. Agents Chemother. 2016, 60, 6635-6649. doi: 10.1128/AAC.01224-16
  6. Hart C.J.S., Munro T., Andrews K.T., Ryan J.H., Riches A.G., Skinner-Adams T.S. Int. J. Parasitol. Drugs Drug. Resist. 2017, 7, 83-89. doi: 10.1016/j.ijpddr.2017.01.005
  7. Ashwell G.J., Gandolfo D.S. J. Mater. Chem. 2002, 12, 411-415. doi: 10.1039/b109872c
  8. Ashwell G.J., Maxwell A.A., Green A. J. Mater. Chem. 2002, 12, 2192-2196. doi: 10.1039/b200565b
  9. Ashwell G.J., Ranjan R., Whittam A.J., Gandolfo D.S. J. Mater. Chem. 2000, 10, 63-68. doi: 10.1039/a902954k
  10. Hsin L.-W., Chang L.-T., Rothman R.B., Dersch C.M., Fishback J.A., Matsumoto R.R. J. Med. Chem. 2010, 53, 1392-1396. doi: 10.1021/jm901503e
  11. Coumar M.S., Tsai M.-T., Chu C.-Y., Uang B.-J, Lin W.-H., Chang C.-Y., Chang T.-Y., Leou J.-S., Teng C.-H., Wu J.-S., Fang M.-Y., Chen C.-H., Hsu J.T.-A., Wu S.-Y., Chao Y.-S., Hsieh H.-P. Chem. Med. Chem. 2010, 5, 255-267. doi: 10.1002/cmdc.200900339
  12. Дяченко И.В., Дяченко В.Д. ЖОрХ. 2017, 53, 1735-1754.
  13. Dyachenko I.V., Dyachenko V.D. Russ. J. Org. Chem. 2017, 53, 1769-1787. doi: 10.1134/S1070428017120016
  14. Дяченко И.В., Калашник И.Н., Дяченко В.Д., Дороватовский П.В., Хрусталев В.Г., Ненайденко В.Г. ЖОрХ. 2019, 55, 1273-1286.
  15. Dyachenko I.V., Kalashnik I.N., Dyachenko V.D., Dorovatovskii P.V., Khrustalev V.N., Nenajdenko V.G. Russ. J. Org. Chem. 2019, 55, 1177-1188. doi: 10.1134/S1070428019080177
  16. Ненайденко В.Г. Усп. хим. 2020, 89, 1274-1336.
  17. Nenajdenko V.G. Russ. Chem. Rev. 2020, 89, 1274-1336. doi: 10.1070/RCR5010.
  18. Литвинов В.П., Доценко В.В., Кривоколыско С.Г. Химия тиенопиридинов и родственных систем. М.: Наука, 2006.
  19. Rappoport Z. Acc. Chem. Res. 1992, 25, 474-479. doi: 10.1021/ar00022a007
  20. Химическая энциклопедия. В 5 Т. Т. 3. Ред. И.Л. Кнунянц. М.: Большая Российская энциклопедия, 1992.
  21. Lockman J.W., Reeder M.D., Suzuki K., Ostanin K., Hoff R., Bhoite, L., Austin H., Baichwal V., Willardsen J.A. Bioorg. Med. Chem. Lett. 2010, 20, 2283-2286. doi: 10.1016/j.bmcl.2010.02.005
  22. Simard J.R., Grütter C., Pawar V., Aust B., Wolf A., Rabiller M., Wulfert S., Robubi A., Klüter S., Ottmann C., Rauh D. J. Am. Chem. Soc. 2009, 131, 18478-18488. doi: 10.1021/ja907795q
  23. Schnute M.E., Cuotahy M.M., Brideau R.J., Homa F.L., Hopkins T.A., Knechtel M.L., Oien N.L., Pitts T.W., Poorman R.A., Wathen M.W., Wieber J.L. J. Med. Chem. 2005, 48, 5794-5804. doi: 10.1021/jm050162b
  24. Mermerian A.H., Case A., Stein R.L., Cuny G.D. Bioorg. Med. Chem. Lett. 2007, 17, 3729-3732. doi: 10.1016/j.bmcl.2007.04.027
  25. Bruker, SAINT, Bruker AXS Inc., Madison, 2013.
  26. Krause L., Herbst-Irmer R., Sheldrick G.M., Stalke D. J. Appl. Crystallogr. 2015, 48, 3-10. doi: 10.1107/S1600576714022985
  27. Spek A.L. PLATON. A Multipurpose Crystallographic Tool. The Netherlands: Utrecht University, 2015.
  28. Sheldrick G.M. Acta Crystallogr., Sect. C. 2015, 71, 3-8. doi: 10.1107/S2053229614024218

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML

Declaração de direitos autorais © Russian Academy of Sciences, 2023