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Diastereoselective Synthesis of 3,4-Dıbenzoil-3,4-Dihydro-1H-Spiro [Benzo[cd]Indol-5,3'-Indoline]-2,2’(2aH)-Diones

Yıl 2019, Cilt: 1 Sayı: 1, 20 - 23, 01.02.2019

Öz

Diastereoselective syntheses of 3,4-dibenzoyl-3,4-dihydro-1H-spiro[benzo[cd]indole-5,3'-indoline]-2,2'(2aH)-dionesin boiling DMF have been carried out starting with 3-(2-phenyl-2-oxoethylidene)indolin-2-ones via a Diels-Alder addition reaction. Theoretical and practical investigations of structure-activity relationships in the group of synthesizedspirooxindoleshave been performed.

Kaynakça

  • Macaev F., Geronikaki A., Sucman N. Recent application of isatins in synthesis of functionalized spirocyclicoxindoles. Chapter in „Targets in heterocycliic systems. Chemistry and Properties”. Ed. O. A. Attanasi and D. Spinelli. Italian Chemical Society, 2011, nr 15, 294-326.
  • Millemaggi A., Taylor R.J.K.3-Alkenyl-oxindoles: natural products, pharmaceuticals, and recent synthetic advances in tandem/telescoped approaches. Eur. J. Org. Chem. 2010, 24, 4527-4547.
  • HanschC.,Sammes P., Taylor J. Comprehensive Medicinal Chemistry. Oxford: Pergamon, 1990. vol. 6. 756 p.
  • Radul O., Junghietu G., Rehter M. Buhaniuk S.A simple way to obtain 1-substituted isatins. Chem. Heterocycl. Comp. 1983, 3, 353-355.
  • Sucman N., Radul O., Pogrebnoi S., Viher V., Gdaniec M., Simonov Iu., Macaev F. The synthesis and the structure of the 1-ethyl-3-(2-oxo-2-phenyletyliden)-2-indolinone, the product of the [2+4]-cycloaddition.All-Russian conference with international participation “Chemistry and Medicine”. 2010. Ufa: Russian Academy of Sciences. p. 317.
  • Macaev F., Ribkovskaia Z., Pogrebnoi S., Boldescu V., Rusu G., Shvets N., Dimoglo A., Geronikaki A., Reynolds R. The structure-antituberculosis activity relationships study in a series of 5-aryl-2-thio-1,3,4-oxadiazole derivatives. Bioorganic and Medicinal Chemistry. 2011, 19, 6792-6807.
  • Macaev F., Rusu G., Pogrebnoi S., Gudima A., Stingaci E., Vlad L., Shvets N., Kandemirli F., Dimoglo A., Reynolds R. Synthesis of Novel 5-Aryl-2-thio-1,3,4-Oxadiazoles and its Structure-Anti-mycobacterial Activity study. Bioorganic and Medicinal Chemistry. 2005, 13, 4842-4850.
  • Geronikaki A., Babaev E., Dearden J., Dehaen W., Filimonov D., Galaeva I., Krajneva V., Lagunin A., Macaev F., Molodavkin G., Poroikov V., Pogrebnoi S., Saloutin V., Stepanchikova A., Stingaci E., Tkach N., Vlad L., Voronina T. Design, synthesis, computational and biological evaluation of new anxiolytics. Bioorganic and Medicinal Chemistry. 2004, 12, 6559-6568.
  • Geronikaki A., Dearden J., Filimonov D., Galaeva I., Garibova T., Gloriozova T., Krajneva V., Lagunin A., Macaev F., Molodavkin G., Poroikov V., Pogrebnoi S., Shepeli F., Voronina T., Tsitlakidou M., Vlad L. Design of new cognition enhancers: from computer prediction to synthesis and biological evaluation. J. Med. Chem. 2004, 47, 2870-2876.
  • MacaevF., RadulO., ShterbetI., PogrebnoiS., SucmanN., MalinovskiiS., BarbaA., Gdaniec M.. Synthesis and structure of new oxoindoles. Chem. Heterocycl. Comp., 2007, 43(3), 298-305
Yıl 2019, Cilt: 1 Sayı: 1, 20 - 23, 01.02.2019

Öz

Kaynakça

  • Macaev F., Geronikaki A., Sucman N. Recent application of isatins in synthesis of functionalized spirocyclicoxindoles. Chapter in „Targets in heterocycliic systems. Chemistry and Properties”. Ed. O. A. Attanasi and D. Spinelli. Italian Chemical Society, 2011, nr 15, 294-326.
  • Millemaggi A., Taylor R.J.K.3-Alkenyl-oxindoles: natural products, pharmaceuticals, and recent synthetic advances in tandem/telescoped approaches. Eur. J. Org. Chem. 2010, 24, 4527-4547.
  • HanschC.,Sammes P., Taylor J. Comprehensive Medicinal Chemistry. Oxford: Pergamon, 1990. vol. 6. 756 p.
  • Radul O., Junghietu G., Rehter M. Buhaniuk S.A simple way to obtain 1-substituted isatins. Chem. Heterocycl. Comp. 1983, 3, 353-355.
  • Sucman N., Radul O., Pogrebnoi S., Viher V., Gdaniec M., Simonov Iu., Macaev F. The synthesis and the structure of the 1-ethyl-3-(2-oxo-2-phenyletyliden)-2-indolinone, the product of the [2+4]-cycloaddition.All-Russian conference with international participation “Chemistry and Medicine”. 2010. Ufa: Russian Academy of Sciences. p. 317.
  • Macaev F., Ribkovskaia Z., Pogrebnoi S., Boldescu V., Rusu G., Shvets N., Dimoglo A., Geronikaki A., Reynolds R. The structure-antituberculosis activity relationships study in a series of 5-aryl-2-thio-1,3,4-oxadiazole derivatives. Bioorganic and Medicinal Chemistry. 2011, 19, 6792-6807.
  • Macaev F., Rusu G., Pogrebnoi S., Gudima A., Stingaci E., Vlad L., Shvets N., Kandemirli F., Dimoglo A., Reynolds R. Synthesis of Novel 5-Aryl-2-thio-1,3,4-Oxadiazoles and its Structure-Anti-mycobacterial Activity study. Bioorganic and Medicinal Chemistry. 2005, 13, 4842-4850.
  • Geronikaki A., Babaev E., Dearden J., Dehaen W., Filimonov D., Galaeva I., Krajneva V., Lagunin A., Macaev F., Molodavkin G., Poroikov V., Pogrebnoi S., Saloutin V., Stepanchikova A., Stingaci E., Tkach N., Vlad L., Voronina T. Design, synthesis, computational and biological evaluation of new anxiolytics. Bioorganic and Medicinal Chemistry. 2004, 12, 6559-6568.
  • Geronikaki A., Dearden J., Filimonov D., Galaeva I., Garibova T., Gloriozova T., Krajneva V., Lagunin A., Macaev F., Molodavkin G., Poroikov V., Pogrebnoi S., Shepeli F., Voronina T., Tsitlakidou M., Vlad L. Design of new cognition enhancers: from computer prediction to synthesis and biological evaluation. J. Med. Chem. 2004, 47, 2870-2876.
  • MacaevF., RadulO., ShterbetI., PogrebnoiS., SucmanN., MalinovskiiS., BarbaA., Gdaniec M.. Synthesis and structure of new oxoindoles. Chem. Heterocycl. Comp., 2007, 43(3), 298-305
Toplam 10 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Bitki Bilimi, Ziraat Mühendisliği, Ziraat, Veterinerlik ve Gıda Bilimleri, Bahçe Bitkileri Yetiştirme ve Islahı, Tarım Politikaları
Bölüm Makaleler
Yazarlar

Natalia Sucman Bu kişi benim

Vsevolod Pogrebno Bu kişi benim

Veceslav Boldescu Bu kişi benim

Fliur Macaev Bu kişi benim

Yayımlanma Tarihi 1 Şubat 2019
Gönderilme Tarihi 10 Aralık 2018
Yayımlandığı Sayı Yıl 2019 Cilt: 1 Sayı: 1

Kaynak Göster

APA Sucman, N., Pogrebno, V., Boldescu, V., Macaev, F. (2019). Diastereoselective Synthesis of 3,4-Dıbenzoil-3,4-Dihydro-1H-Spiro [Benzo[cd]Indol-5,3’-Indoline]-2,2’(2aH)-Diones. Uluslararası Anadolu Ziraat Mühendisliği Bilimleri Dergisi, 1(1), 20-23.