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Synthesis and Biological Activities of Some Novel Spiro Heterocyclic Pyrrolizidine Derivatives of 11H-indeno[1,2-b]quinoxaline through 1,3-Dipolar Cycloaddition
Corresponding Author(s) : Chhagan Lal
Asian Journal of Chemistry,
Vol. 32 No. 5 (2020): Vol 32 Issue 5
Abstract
The synthesis of spiropyrrolidines by the Knoevenagel condensation has been reported as highly bioactive natural and synthetic organic products. The synthesis was initiated by Knoevenagel condensation of indole-2-one with an appropriate benzaldehyde in presence of L-proline to afford spiropyrrolidines. Herein, a design and pathway of syntheses of a library of spiropyrrolidines bearing spiro heterocyclic indeno[1,2-b]quinoxaline-11-one motifs were reported, which also demonstrated an exceptional inhibitory activity against the anticancer cells. A novel series of dispiroindenoquinoxaline pyrrolizidines were synthesized by the condensation of indeno[1,2-b]quinoxalin-11-one and starting material (a product of ninhydrin and aldehyde derivatives). The structure of the synthesized compounds was established by spectral data.
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- P. Pattanaik, S. Nayak, D.R. Mishra, P. Panda, B.P. Raiguru, N. Priyadarsini Mishra, S. Mohapatra, N.A. Mallampudi, C.S. and Purohit, Tetrahedron Lett., 59, 2688 (2018); https://doi.org/10.1016/j.tetlet.2018.05.087
- A.V. Velikorodov, N.N. Stepkina, E.A. Shustova and V.A. Ionova, Russ. J. Org. Chem., 51, 674 (2015); https://doi.org/10.1134/S1070428015050164
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- H. Liu, G.L. Dou and D.Q. Shi, J. Comb.Chem., 12, 292 (2010); https://doi.org/10.1021/cc900195t
- A.R. Suresh Babu and R. Raghunathan, Synth. Commun., 38, 1433 (2008); https://doi.org/10.1080/00397910801914327
- A.M. Akondi, S. Mekala, M.L. Kantam, R. Trivedi, L.R. Chowhane and A. Das, New J. Chem., 41, 873 (2017); https://doi.org/10.1039/c6nj02869a
- M. Moemeni, H. Arvinnezhad, S. Samadi, M. Tajbakhsh, K. Jadidi and H.R. Khavasi, J. Heterocycl. Chem., 49, 190 (2012); https://doi.org/10.1002/jhet.685
- P. Saraswat, G. Jeyabalan, M.Z. Hassan, M.U. Rahman and N.K. Nyola, Synth. Commun.,46, 1643 (2016); https://doi.org/10.1080/00397911.2016.1211704
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- K. Karthikeyan, P.M. Sivakumar, M. Doble and P.T. Perumal, Eur. J. Med. Chem., 45, 3446 (2010); https://doi.org/10.1016/j.ejmech.2010.04.035
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- L.R. Wen, Y.J. Shi, G.Y. Liu and M. Li, J. Org. Chem., 77, 4252 (2012); https://doi.org/10.1021/jo202665q
- H. Liu, G.L. Dou and D.Q. Shi, J. Comb.Chem., 12, 633 (2010); https://doi.org/10.1021/cc100035q
- K.E. Kolb, K.W. Field and P.F. Schatz, J. Chem. Educ., 67, A304 (1990); https://doi.org/10.1021/ed067pA304
- K. Selvakumar, V. Vaithiyanathan and P. Shanmugam, Chem. Commun., 46, 2826 (2010); https://doi.org/10.1039/B924066G
- A. Dömling, Chem. Rev., 106, 17 (2006); https://doi.org/10.1021/cr0505728
- E.V. Dalessandro, H.P. Collin, L.G.L. Guimarães, M.S. Valle and J.R. Pliego, J. Phys. Chem. B, 121, 5300 (2017); https://doi.org/10.1021/acs.jpcb.7b03191
- Y. Huang, Y.-X.Huang, J. Sun and C.-G. Yan, New J. Chem., 43, 8903 (2019); https://doi.org/10.1039/C9NJ00994A
- I.S. Santos, F.S. Guerra, L.F. Bernardino, P.D. Fernandes, L. Hamerski and B.V. Silva, J. Brazilian Chem. Soc., 198-209 (2019); https://doi.org/10.21577/0103-5053.20180153
References
P. Pattanaik, S. Nayak, D.R. Mishra, P. Panda, B.P. Raiguru, N. Priyadarsini Mishra, S. Mohapatra, N.A. Mallampudi, C.S. and Purohit, Tetrahedron Lett., 59, 2688 (2018); https://doi.org/10.1016/j.tetlet.2018.05.087
A.V. Velikorodov, N.N. Stepkina, E.A. Shustova and V.A. Ionova, Russ. J. Org. Chem., 51, 674 (2015); https://doi.org/10.1134/S1070428015050164
A.Y. Barkov, N.S. Zimnitskiy, V.Y. Korotaev, I.B. Kutyashev, V.S. Moshkin and V.Y. Sosnovskikh, Chem. Heterocycl. Compd., 53, 451 (2017); https://doi.org/10.1007/s10593-017-2074-0
H. Liu, G.L. Dou and D.Q. Shi, J. Comb.Chem., 12, 292 (2010); https://doi.org/10.1021/cc900195t
A.R. Suresh Babu and R. Raghunathan, Synth. Commun., 38, 1433 (2008); https://doi.org/10.1080/00397910801914327
A.M. Akondi, S. Mekala, M.L. Kantam, R. Trivedi, L.R. Chowhane and A. Das, New J. Chem., 41, 873 (2017); https://doi.org/10.1039/c6nj02869a
M. Moemeni, H. Arvinnezhad, S. Samadi, M. Tajbakhsh, K. Jadidi and H.R. Khavasi, J. Heterocycl. Chem., 49, 190 (2012); https://doi.org/10.1002/jhet.685
P. Saraswat, G. Jeyabalan, M.Z. Hassan, M.U. Rahman and N.K. Nyola, Synth. Commun.,46, 1643 (2016); https://doi.org/10.1080/00397911.2016.1211704
S.-Y. Li, J.M. Finefield, J.D. Sunderhaus, T.J. Mcafoos, R.M. Williams and D.H. Sherman, J. Med. Chem., 134, 788 (2012); https://doi.org/10.1021/ja2093212
K. Karthikeyan, P.M. Sivakumar, M. Doble and P.T. Perumal, Eur. J. Med. Chem., 45, 3446 (2010); https://doi.org/10.1016/j.ejmech.2010.04.035
R.T. Pardasani, P. Pardasani, V. Chaturvedi, S.K. Yadav, A. Saxena and I. Sharma, Heteroatom Chem., 14, 36 (2003); https://doi.org/10.1002/hc.10063
L.R. Wen, Y.J. Shi, G.Y. Liu and M. Li, J. Org. Chem., 77, 4252 (2012); https://doi.org/10.1021/jo202665q
H. Liu, G.L. Dou and D.Q. Shi, J. Comb.Chem., 12, 633 (2010); https://doi.org/10.1021/cc100035q
K.E. Kolb, K.W. Field and P.F. Schatz, J. Chem. Educ., 67, A304 (1990); https://doi.org/10.1021/ed067pA304
K. Selvakumar, V. Vaithiyanathan and P. Shanmugam, Chem. Commun., 46, 2826 (2010); https://doi.org/10.1039/B924066G
A. Dömling, Chem. Rev., 106, 17 (2006); https://doi.org/10.1021/cr0505728
E.V. Dalessandro, H.P. Collin, L.G.L. Guimarães, M.S. Valle and J.R. Pliego, J. Phys. Chem. B, 121, 5300 (2017); https://doi.org/10.1021/acs.jpcb.7b03191
Y. Huang, Y.-X.Huang, J. Sun and C.-G. Yan, New J. Chem., 43, 8903 (2019); https://doi.org/10.1039/C9NJ00994A
I.S. Santos, F.S. Guerra, L.F. Bernardino, P.D. Fernandes, L. Hamerski and B.V. Silva, J. Brazilian Chem. Soc., 198-209 (2019); https://doi.org/10.21577/0103-5053.20180153