RAS Chemistry & Material ScienceЖурнал общей химии Russian Journal of General Chemistry

  • ISSN (Print) 0044-460X
  • ISSN (Online) 3034-5596

Synthesis of Formylphenyl 1-Oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylates and Their (E)-1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-yliminomethyl Derivatives

PII
10.31857/S0044460X24070016-1
DOI
10.31857/S0044460X24070016
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 94 / Issue number 7
Pages
786-804
Abstract
Formylphenyloxohydroepoxyisoindole carboxylates were prepared by the reaction of 4-hydroxy-3-methoxy-, 4-hydroxy-3-ethoxy- and 3-hydroxy-4-methoxybenzaldehydes with substituted isoindolecarboxylic acids {2-methyl-1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic, 2-(3,4-dimethoxyphenethyl)1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic, 2-(benzo[d][1,3]dioxol-5-ylmethyl)-1-oxo1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic, 6-oxo-3,4,6,6a,7,8-hexahydro-2H,10bH-8,10a-epoxy[1,3]oxazino[2,3-a]isoindole-7-carboxylic, 2-(2,3-dichlorobenzyl)-1-oxo-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic} in dichloromethane in the presence of dicyclohexylcarbodiimide. The corresponding (E)-azomethines were synthesized by condensation of formylphenyloxohydroepoxyisoindole carboxylates with 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one in methanol.
Keywords
изоиндол 4-аминоантипирин ванилин ванилаль изованилин сложные эфиры азометины лекарственные средства
Date of publication
17.09.2025
Year of publication
2025
Number of purchasers
0
Views
14

References

  1. 1. Makhoba X.H., Viegas C., Jr., Mosa R.A., Viegas F.P.D., Pooe O.J. // Drug Des Devel Ther. 2020. Vol. 14. P. 3235. doi 10.2147/DDDT.S257494
  2. 2. Talevi A. // Front. Pharmacol. 2015. Vol. 6. P. 205. doi 10.3389/fphar.2015.00205
  3. 3. Csende F., Porkolab A. // Der Pharma Chem. 2018. Vol. 10. N 6. P. 43.
  4. 4. Kocyigit U.M., Budak Y., Gürdere M.B., Tekin Ş., Kőprülü T.K., Evtürk F., Őzcan K., Gülçin I., Ceylan M. // Bioorg. Chem. 2017. Vol. 70. P. 118. doi 10.1016/ j.bioorg.2016.12.001
  5. 5. Süloğlu A.K., Selmanoglu G., Gündoğdu Ő., Kishali N.H., Girgin G., Palabiyik S., Tan A., Kara Y., Baydar T. // Arch. Pharm. 2020. P. e2000065. doi 10.1002/ardp.202000065
  6. 6. Tan A., Yaglioglu A.S., Kishali N.H., Sahin E., Kara Y. // Med. Chem. 2020. Vol. 16. P. 69. doi 10.2174/ 1573406415666181206115638
  7. 7. Szkatuła D., Kvzyźak E., Stanowska P., Duba M., Wiatrak B. // Int. J. Mol. Sci. 2021. Vol. 22. P. 7678. doi 10.3390/ijms22147678
  8. 8. Portevin B., Tordjman C., Pastourean P., Bonnet J., Nanteuil G.D. // J. Med. Chem. 2000. Vol. 43. P. 4582. doi 10.1021/jm990965x
  9. 9. Singha L.S., Bareh V., Alam F. // Int. J. Pharm. Sci. Res. 2021. Vol. 12. N 10. P. 5341. doi 10.13040/ IJPSR.0975-8232.12(10).5341-52
  10. 10. Sakthivel A., Jeyasubramanian K., Thangagiri B., Dhaveethu Raja J. // J. Mol. Struc. 2020. Vol. 1222. Art. ID 128885. doi 10.1016/j.molstruc.2020.128885
  11. 11. Aguilar-Llanos E., Carrera-Pacheco S.E., González-Pastor R., Zúñiga-Miranda J., Rodríguez-Pólit C., Mayorga-Ramos A., Carrillo-Naranjo O., Guamán L.P., Romero-Benavides J.C., Cevallos-Morillo C., Echeverría G.A., Piro O.E., Alcívar-León Ch.D., Heredia-Moya J. // ACS Omega. 2023. Vol. 8. N 45. P. 42632. doi 10.1021/acsomega.3c05372
  12. 12. Teran R., Guevara R., Mora J., Dobronski L., Barreiro-Costa O., Beske T., Pérez-Barrera J., Araya-Maturana R., Rojas-Silva P., Poveda A., Heredia-Moya J. // Molecules. 2019. Vol. 24. N 15. P. 2696. doi 10.3390/molecules24152696
  13. 13. Çakmak R., Başaran E., Boğa, M., Erdoğan Ö., Çınar E., Çevik Ö. // Russ. J. Bioorg. Chem. 2022. Vol. 48. P. 334. doi 10.1134/S1068162022020182
  14. 14. Kumar R., Sing H., Mazumder A., Salahuddin, Yadav R.K. // Top. Curr. Chem. 2023. Vol. 381. Article no. 12. doi 10.1007/s4061-023-00422-z
  15. 15. Варламов А.В., Болтухина Е.В., Зубков Ф.И., Сидоренко Н.В., Чернышев А.И., Грудинин Д.Г. // ХГС. 2004. № 1. C. 27; Varlamov A.V., Boltukhina E.V., Zubkov F.I., Sidorenko N.V., Chernyshev A.I., Grudinin D.G. // Chem. Heterocycl. Compd. 2004. Vol. 40. N 1. P. 22. doi 10.1023/ B:COHC.0000023763.75894.63
  16. 16. Sarang P., Yadav A., Patil P., Krishna U., Trivedi G., Salunkhe M. // Synthesis. 2007. N 7. P. 1091. doi 10.1055/s-2007-965950
  17. 17. Zubkov F.I., Zaytsev V.P., Nikitina E.V., Khrustalev V.N., Gozun S.V., Boltukhina E.V., Varlamov A.V. // Tetrahedron. 2011. Vol. 67. N 47. P. 9148. doi 10.1016/j.tet.2011.09.099
  18. 18. Zubkov F.I., Nikitina E.V., Galeev T.R., Zaytsev V.P., Khrustalev V.N., Novikov R.A., Orlova D.N., Varlamov A.V. // Tetrahedron. 2014. Vol. 70. N 8. P. 1659. doi 10.1016/ j.tet.2014.01.008
  19. 19. Hizartzidis L., Tarleton M., Gordona C.P., McCluskey A. // RSC Adv. 2014. Vol. 4. P. 9709. doi 10.1039/C3RA47657J
  20. 20. Hizartzidis L., Gilbert J., Gordon C.P., Sakoff J.A., McCluskey A. // ChemMedChem. 2019. Vol. 14. N 12. P. 1152. doi 10.1002/cmdc.201900180
  21. 21. Alam M.S., Lee D.-U. // J. Chem. Crystallogr. 2011. Vol. 42. N 2. P. 93. doi10.1007/s10870-011-0209-1
  22. 22. Upadhyay A., Kar P.K., Dash S. // Spectrochim. Acta (A). 2020. Vol. 233. Art. ID 118231. doi 10.1016/ j.saa.2020.118231
  23. 23. Han J.-R., Zhen X.-L., Tian X., Li F., Liu S.-X. // Acta Crystallogr. 2007. Vol. 63. N 10. P. 4035. doi 10.1107/s1600536807043796
  24. 24. Kamdem D., Gage D. // Planta Medica. 2007. Vol. 61. N 6. P. 574. doi 10.1055/s-2006-959379
  25. 25. Panten J., Surburg H. In: Ullmann’s Encyclopedia of Industrial Chemistry, online version. Hoboken: John Wiley & Sons, Inc., 2015. P. 136. doi 10.1002/ 14356007.a11_141
  26. 26. Murray М. // Curr. Drug Metab. 2000. Vol. 1. N 1. P. 67. doi 10.2174/1389200003339270
  27. 27. Miklós F., Hetényi A., Sohár P., Stájer G. // Monatsh. Chem. 2004. Vol. 135. N 7. P. 839. doi 10.1007/ s00706-003-0161-7
  28. 28. Zilch H., Poll T., Schaefer W., Koenig B., Leser U. Pat. WO 9215310 (1992).
QR
Translate

Индексирование

Scopus

Scopus

Scopus

Crossref

Scopus

Higher Attestation Commission

At the Ministry of Education and Science of the Russian Federation

Scopus

Scientific Electronic Library