Abstract
In the present review the data concerning selective synthetic transformations of isatins to 2-oxindoles, and studies of their biological activity are summarized.
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Y. Wei, M. Shi, Chem. Rev., 2013, 113, 6659.
A. D. Allen, T. T. Tidwell, Chem. Rev., 2013, 113, 7287.
X. Tian, P. Melchiorre, Angew. Chem., Int. Ed., 2013, 52, 5360.
I. Saidalimu, X. Fang, X.-P. He, J. Liang, X. Yang, F. Wu, Angew. Chem., Int. Ed., 2013, 52, 5566.
W. Sun, G. Zhu, C. Wu, G. Li, L. Hong, R. Wang, Angew. Chem., Int. Ed., 2013, 52, 8633.
K. Shen, X. Liu, L. Lin, X. Feng, Chem. Sci., 2012, 3, 327.
G. S. Singh, Z. Y. Desta, Chem. Rev., 2012, 112, 6104.
A. D. Borthwick, Chem. Rev., 2012, 112, 3641.
S. Peddibhotla, Curr. Bioact. Compd., 2009, 5, 20.
C. Avendaco, J. C. Menendez, Curr. Org. Synth., 2004, 1, 65.
N. R. Ball-Jones, J. J. Badillo, A. K. Franz, Org. Biomol. Chem., 2012, 10, 5165.
R. Dalpozzo, G. Bartoli, G. Bencivenni, Chem. Soc. Rev., 2012, 41, 7247.
A. Kumar, S. S. Chimn, RSC Adv., 2012, 2, 9748.
F. Macaev, A. Geronikaki, N. Sucman, in Targets in Heterocycliic Systems. Chemistry and Properties, Eds O. A. Attanasi, D. Spinelli, Pesaro-Urbino, Societa Chimica Italiana, 2011, 15, 294.
F. Macaev, in Selected Methods for Synthesis and Modification of Heterocycles, IBS PRESS, Moscow, 2004, 3, 75.
F. Z. Macaev, O. M. Radul, A. P. Gudima, Russ. Chem. Bull. (Int. Ed.), 2008, 57, 1571 [Izv. Akad. Nauk, Ser. Khim., 2008, 1540].
Y. Kamano, H.-P. Zhang, Y. Ichihara, H. Kizu, K. Komiyama, G. R. Pettit, Tetrahedron Lett., 1995, 36, 2783.
F. Z. Macaev, O. M. Radul, M. Gdanets, S. T. Malinovskii, A. P. Gudima, Zhurn. Strukt. Khim., 2006, 47, 803 [Russ. J. Struct. Chem. (Engl. Transl.), 2006, 47, 769].
F. Z. Macaev, A. Geronikaki, O. M. Radul, A. P. Gudima, Abstr. of the 4th Eurasian Meeting on Heterocyclic Chemistry (Thessaloniki, Greece, 27–31 August 2006), 175.
K. C. Joshi, A. Dandia, S. J. Bhagat, Indian Chem. Soc., 1990, 67, 753.
F. Z. Macaev, O. M. Radul, I. N. Shterbets, S. I. Pogrebnoi, N. S. Sucman, S. T. Malinovskii, A. N. Barba, M. Gdanets, Khim. Geterotsikl. Soed., 2007, 374 [Chem. Heterocycl. Compd. (Engl. Transl.), 2007, 43, 298].
M. A. Rehter, F. Z. Macaev, F. B. Babilev, G. N. Grushetskaya, S. V. Rudakov, Khim. Geterotsikl. Soed., 1996, 483 [Chem. Heterocycl. Compd. (Engl. Transl.), 1996, 32, 418].
M. A. Rehter, B. A. Rehter, I. G. Yazlovetskii, A. A. Panasenko, F. Z. Macaev, Khim. Geterotsikl. Soed., 1998, 308 [Chem. Heterocycl. Compd. (Engl. Transl.), 1998, 38, 275].
C. L. Woodard, Z. Li, A. K. Kathcart, J. Terrell, L. Gerena, M. Lopez-Sanchez, D. E. Kyle, A. K. Bhattacharjee, D. A. Nichols, W. Ellis, S. T. Prigge, J. A. Geyer, N. C. Waters, J. Med. Chem., 2003, 46, 3877.
D. Prodius, F. Macaev, E. Stingaci, V. Pogrebnoi, V. Mereacre, G. Novitchi, G. E. Kostakis, C. E. Anson, A. K. Powell, Chem. Commun., 2013, 49, 1915.
D. Prodius, F. Macaev, Y. Lan, G. Novitchi, S. Pogrebnoi, E. Stingaci, V. Mereacre, G. E. Kostakis, C. E. Anson, A. K. Powell, Chem. Commun., 2013, 49, 9215.
G. Shanthi, P. T. Perumal, Tetrahedron Lett., 2009, 50, 3959.
V. Sargorovschi, N. Sucman, T. Iudin, E. Stingaci, F. Macaev, Chem. J. Moldova, 2010, 5, 109.
MD Pat. 4062; BOPI, 2010, 8, 21.
P. Shanmugam, V. Vaithiyanathan, B. Viswambharan, Tetrahedron, 2006, 62, 4342.
P. Shanmugam, B. Viswambharan, Synlett, 2008, 18, 2763.
N. S. Sucman, Ph. D. (Chem.) Thesis, Institute of Chemistry, Academy of Sciences of Moldova, Chisinau, 2013, 160 pp.
MD Pat. 2557; BOPI, 2004, 9, 38.
A. Geronikaki, E. Babaev, J. Dearden, W. Dehaen, D. Filimonov, I. Galaeva, V. Krajneva, A. Lagunin, F. Macaev, G. Molodavkin, V. Poroikov, S. Pogrebnoi, V. Saloutin, A. Stepanchikova, E. Stingaci, N. Tkach, T. Voronina, L. Vlad, Bioorg. Med. Chem., 2004, 12, 6559.
O. M. Radul, S. T. Malinovskii, R. Lyubodarskii, F. Z. Macaev, Kristallografiya, 2005, 50, 998 [Crystallogr. Repts (Engl. Transl.), 2005, 50, 923].
G. Zhungietu, Rev. Roum. Chem., 2001, 46, 517.
T. Jiang, K. L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T. Y.-H. Wu, Y. He, Bioorg. Med. Chem. Lett., 2006, 16, 2105.
T. Jiang, K. L. Kuhen, K. Wolff, H. Yin, K. Bieza, J. Caldwell, B. Bursulaya, T. Tuntland, K. Zhang, D. Karanewsky, Y. He, Bioorg. Med. Chem. Lett., 2006, 16, 2109.
G. Kumari, M. Modi, S. K. Gupta, R. K. Singh, Eur. J. Med. Chem., 2011, 46, 1181.
C. Marti, E. M. Carreira, J. Am. Chem. Soc., 2005, 127, 11505.
S. Chen, J. Ma, J. Wang, Tetrahedron Lett., 2008, 49, 6781.
S. Muthusamy, D. Azhagan, B. Gnanaprakasam, E. Suresh, Tetrahedron Lett., 2010, 51, 5662.
F. Z. Macaev, N. S. Sucman, E. P. Styngach, V. S. Pogrebnoi, Materials of Cluster of Conferences on the Organic Chemistry “OrgKhim-2013” (St. Petersburg, Repino, June 17–21, 2013), St. Petersburg, Repino, 2013, 180.
S. Surmava, P. Elefthetiou, A. Geronikaki, C. Petrou, F. Macaev, N. Sucman, Abstr. of the XVIII Int. AIDS Conference (Vienna, 18–23 July 2010), 56.
A. Noole, N. S. Sucman, M. A. Kabeshov, T. Kanger, F. Z. Macaev, A. V. Malkov, Chem. Eur. J., 2012, 18, 14929.
R. Boon, Antiviral Chem. Chemother., 1997, 8, 5.
O. M. Radul, S. T. Malinovskii, R. Lyuboradskii, F. Z. Macaev, Zh. Strukt. Khim., 2005, 46, 753 [Russ. J. Struct. Chem. (Engl. Transl.), 2005, 46, 732].
O. Radul, N. Sucman, S. Pogrebnoi, A. Barba, A. Geronikaki, F. Macaev, Chem. J. Moldova, 2011, 6, 101.
O. M. Radul, G. I. Zhungietu, M. A. Rehter, S. M. Buhanyuk, Khim. Geterotsikl. Soed., 1983, 353 [Chem. Heterocycl. Compd. (Engl. Transl.), 1983, 3, 353].
W.-B. Chen, Z.-J. Wu, Q.-L. Pei, L.-F. Cun, X.-M. Zhang, W.-C. Yuan, Org. Lett., 2010, 12, 3132.
F. Macaev, N. Sucman, F. Shepeli, M. Zveaghintseva, V. Pogrebnoi, Symmetry, 2011, 3, 165.
K. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith, T. A. Smitka, J. Am. Chem. Soc., 1994, 116, 9935.
J. I. Jimenez, U. Huber, R. E. Moore, G. M. L. Patterson, J. Natur. Prod., 1999, 62, 569.
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According to the materials of the Cluster of Conferences on Organic Chemistry “OrgKhim-2013” (June 17–21, 2013, St. Petersburg, Repino).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0015–0025, January, 2014.
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Macaev, F.Z., Sucman, N.S. & Boldescu, V.V. Selective transformations of isatins to substituted 2-oxindoles. Russ Chem Bull 63, 15–25 (2014). https://doi.org/10.1007/s11172-014-0389-x
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DOI: https://doi.org/10.1007/s11172-014-0389-x