메뉴 건너뛰기




Volumn 16, Issue 10, 2011, Pages 8745-8757

Facile synthesis of functionalized spiropyrrolizidine oxindoles via a three-component tandem cycloaddition reaction

Author keywords

Cycloaddition; Isatin; Spiropyrrolizidine oxindoles

Indexed keywords


EID: 80054881561     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16108745     Document Type: Article
Times cited : (20)

References (44)
  • 1
    • 0032143275 scopus 로고    scopus 로고
    • Tryprostatin A, a specific and novel inhibitor of microtubule assembly
    • Usui, T.; Kondoh, M.; Cui, C. B.; Mayumi, T.; Osada, H. Tryprostatin A, a specific and novel inhibitor of microtubule assembly. Biochem. J. 1998, 333, 543-538.
    • (1998) Biochem. J. , vol.333 , pp. 543-538
    • Usui, T.1    Kondoh, M.2    Cui, C.B.3    Mayumi, T.4    Osada, H.5
  • 3
    • 0038392407 scopus 로고    scopus 로고
    • Construction of spiro[pyrrolidine-3, 3-oxindoles]-recent applications to the synthesis of oxindole alkaloids
    • Marti, C.; Carreira, E. M. Construction of spiro[pyrrolidine-3, 3-oxindoles]-recent applications to the synthesis of oxindole alkaloids. Eur. J. Org. Chem. 2003, 2003, 2209-2219.
    • (2003) Eur. J. Org. Chem. , vol.2003 , pp. 2209-2219
    • Marti, C.1    Carreira, E.M.2
  • 4
    • 52449097257 scopus 로고    scopus 로고
    • Discovery of antimycobacterial spiro-piperidin-4-ones: An atom economic, stereoselective synthesis, and biological intervention
    • Kumar, R. R.; Perumal, S.; Senthilkumar, P.; Yogeeswari, P.; Sriram, D. Discovery of antimycobacterial spiro-piperidin-4-ones: An atom economic, stereoselective synthesis, and biological intervention. J. Med. Chem. 2008, 51, 5731-5735.
    • (2008) J. Med. Chem. , vol.51 , pp. 5731-5735
    • Kumar, R.R.1    Perumal, S.2    Senthilkumar, P.3    Yogeeswari, P.4    Sriram, D.5
  • 5
    • 67650504633 scopus 로고    scopus 로고
    • A facile synthesis and antimycobacterial evaluation of novel spiro-pyrido-pyrrolizines and pyrrolidines
    • Kumar, R. R.; Perumal, S.; Senthilkumar, P.; Yogeeswari, P.; Sriram, D. A facile synthesis and antimycobacterial evaluation of novel spiro-pyrido- pyrrolizines and pyrrolidines. Eur. J. Med. Chem. 2009, 44, 3821-3829.
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 3821-3829
    • Kumar, R.R.1    Perumal, S.2    Senthilkumar, P.3    Yogeeswari, P.4    Sriram, D.5
  • 6
    • 72049097924 scopus 로고    scopus 로고
    • Novel three-component domino reactions of ketones, isatin and amino acids: Synthesis and discovery of antimycobacterial activity of highly functionalised novel dispiropyrrolidines
    • Kumar, R. S.; Rajesh, S. M.; Perumal, S.; Banerjee, D.; Yogeeswari, P.; Sriram, D. Novel three-component domino reactions of ketones, isatin and amino acids: Synthesis and discovery of antimycobacterial activity of highly functionalised novel dispiropyrrolidines. Eur. J. Med. Chem. 2010, 45, 411-422.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 411-422
    • Kumar, R.S.1    Rajesh, S.M.2    Perumal, S.3    Banerjee, D.4    Yogeeswari, P.5    Sriram, D.6
  • 7
    • 78449282828 scopus 로고    scopus 로고
    • A facile 1, 3-dipolar cycloaddition of azomethine ylides to 2-arylidene-1, 3-indanediones: Synthesis of dispirooxindolylpyrrolothiazoles and their antimycobacterial evaluation
    • Maheswari, S. U.; Balamurugan, K.; Perumal, S.; Yogeeswari, P.; Sriram, D. A facile 1, 3-dipolar cycloaddition of azomethine ylides to 2-arylidene-1, 3-indanediones: Synthesis of dispirooxindolylpyrrolothiazoles and their antimycobacterial evaluation. Bioorg. Med. Chem. Lett. 2010, 20, 7278-7282.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 7278-7282
    • Maheswari, S.U.1    Balamurugan, K.2    Perumal, S.3    Yogeeswari, P.4    Sriram, D.5
  • 8
    • 78649319292 scopus 로고    scopus 로고
    • A regio-and stereoselective 1, 3-dipolar cycloaddition for the synthesis of novel spiropyrrolothiazolyloxindoles and their antitubercular evaluation
    • Prasanna, P.; Balamurugan, K.; Perumal, S.; Yogeeswari, P.; Sriram, D. A regio-and stereoselective 1, 3-dipolar cycloaddition for the synthesis of novel spiropyrrolothiazolyloxindoles and their antitubercular evaluation. Eur. J. Med. Chem. 2010, 45, 5653-5661.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 5653-5661
    • Prasanna, P.1    Balamurugan, K.2    Perumal, S.3    Yogeeswari, P.4    Sriram, D.5
  • 9
    • 72049094262 scopus 로고    scopus 로고
    • A highly atom economic, chemo-, regio-and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents
    • Karthikeyan, S. V.; Bala, B. D.; Raja, V. P.; Perumal, S.; Yogeeswari, P.; Sriram, D. A highly atom economic, chemo-, regio-and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents. Bioorg. Med. Chem. Lett. 2010, 20, 350-353.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 350-353
    • Karthikeyan, S.V.1    Bala, B.D.2    Raja, V.P.3    Perumal, S.4    Yogeeswari, P.5    Sriram, D.6
  • 10
    • 34248562794 scopus 로고    scopus 로고
    • Synthesis of novel 3′-spirocyclic-oxindole derivatives and assessment of their cytostatic activities
    • DOI 10.1016/j.tet.2007.04.028, PII S0040402007006709
    • Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Synthesis of novel 3'-spirocyclicoxindole derivatives and assessment of their cytostatic activities. Tetrahedron 2007, 63, 5579-5586. (Pubitemid 46755350)
    • (2007) Tetrahedron , vol.63 , Issue.25 , pp. 5579-5586
    • Yong, S.R.1    Ung, A.T.2    Pyne, S.G.3    Skelton, B.W.4    White, A.H.5
  • 12
    • 57949106458 scopus 로고    scopus 로고
    • Regioselective synthesis of dispiro[1H-indene-2, 3'-pyrrolidine-2', 3"-[3H]indole]-1, 2" (1"H)-diones of potential anti-tumor properties
    • Girgis, A. S. Regioselective synthesis of dispiro[1H-indene-2, 3'-pyrrolidine-2', 3"-[3H]indole]-1, 2" (1"H)-diones of potential anti-tumor properties. Eur. J. Med. Chem. 2009, 44, 91-100.
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 91-100
    • Girgis, A.S.1
  • 15
    • 41249097895 scopus 로고    scopus 로고
    • Synthesis of novel spiropyrrolizidines as potent antimicrobial agents for human and plant pathogens
    • Periyasami, G.; Raghunathan, R.; Surendiran, G.; Mathivanan, N. Synthesis of novel spiropyrrolizidines as potent antimicrobial agents for human and plant pathogens. Bioorg. Med. Chem. Lett. 2008, 18, 2342-23425.
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 2342-23425
    • Periyasami, G.1    Raghunathan, R.2    Surendiran, G.3    Mathivanan, N.4
  • 16
    • 78649666112 scopus 로고    scopus 로고
    • Synthesis, characterization, and antimicrobial activity of 3′-(4-(2-substituted thiazol-4-yl) phenyl) spiro[indoline-3, 2′-thiazolidine]-2, 4′-diones
    • Mhaske, P. C.; Shelke, S. H.; Jadhav, R. P.; Raundal, H. N.; Patil, S. V.; Patil, A. A.; Bobade, V. D. Synthesis, characterization, and antimicrobial activity of 3′-(4-(2-substituted thiazol-4-yl) phenyl) spiro[indoline-3, 2′-thiazolidine]-2, 4′-diones. J. Heterocyclic Chem. 2010, 47, 1415-1420.
    • (2010) J. Heterocyclic Chem. , vol.47 , pp. 1415-1420
    • Mhaske, P.C.1    Shelke, S.H.2    Jadhav, R.P.3    Raundal, H.N.4    Patil, S.V.5    Patil, A.A.6    Bobade, V.D.7
  • 17
    • 78649319292 scopus 로고    scopus 로고
    • A regio-and stereoselective 1, 3-dipolar cycloaddition for the synthesis of novel spiropyrrolothiazolyloxindoles and their antitubercular evaluation
    • Prasanna, P.; Balamurugan, K.; Perumal, S.; Yogeeswari, P.; Sriram, D. A regio-and stereoselective 1, 3-dipolar cycloaddition for the synthesis of novel spiropyrrolothiazolyloxindoles and their antitubercular evaluation. Eur. J. Med. Chem. 2010, 45, 5653-5661.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 5653-5661
    • Prasanna, P.1    Balamurugan, K.2    Perumal, S.3    Yogeeswari, P.4    Sriram, D.5
  • 18
    • 0037293565 scopus 로고    scopus 로고
    • Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines
    • DOI 10.1016/S0968-0896(02)00439-X, PII S096808960200439X
    • Raj, A. A.; Raghunathan, R.; Sridevi Kumari, M. R.; Raman, N. Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines. Bioorg. Med. Chem. 2003, 11, 407-419. (Pubitemid 36051031)
    • (2003) Bioorganic and Medicinal Chemistry , vol.11 , Issue.3 , pp. 407-419
    • Amal Raj, A.1    Raghunathan, R.2    SrideviKumari, M.R.3    Raman, N.4
  • 19
    • 78649319737 scopus 로고    scopus 로고
    • Regiospecific synthesis and biological evaluation of spirooxindolopyrrolizidines via [3+2] cycloaddition of azomethine ylide
    • Thangamani, A. Regiospecific synthesis and biological evaluation of spirooxindolopyrrolizidines via [3+2] cycloaddition of azomethine ylide. Eur. J. Med. Chem. 2010, 45, 6120-6126.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 6120-6126
    • Thangamani, A.1
  • 20
    • 33644807569 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part I
    • DOI 10.1016/j.bmcl.2006.01.073, PII S0960894X06001119
    • Jiang, T.; Kuhen, K. L.; Wolff, K.; Yin, H.; Bieza, K.; Caldwell, J.; Bursulaya, B.; Wu, T. Y.; He, Y. Design, synthesis and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part I. Bioorg. Med. Chem. Lett. 2006, 16, 2105-2108. (Pubitemid 43351059)
    • (2006) Bioorganic and Medicinal Chemistry Letters , vol.16 , Issue.8 , pp. 2105-2108
    • Jiang, T.1    Kuhen, K.L.2    Wolff, K.3    Yin, H.4    Bieza, K.5    Caldwell, J.6    Bursulaya, B.7    Wu, T.Y.-H.8    He, Y.9
  • 22
    • 0017079032 scopus 로고
    • Oxindole-3-spiropyrrolidines and piperidines. Synthesis and local anesthetic activity
    • Kornet, M. J.; Thio, A. P. Oxindole-3-spiropyrrolidines and piperidines. Synthesis and local anesthetic activity. J. Med. Chem. 1976, 19, 892-898.
    • (1976) J. Med. Chem. , vol.19 , pp. 892-898
    • Kornet, M.J.1    Thio, A.P.2
  • 27
    • 33749314877 scopus 로고    scopus 로고
    • An efficient synthesis of a spirocyclic oxindole analogue
    • DOI 10.3390/11090700
    • Teng, D.; Zhang, H.; Mendonca, A. An efficient synthesis of a spirocyclic oxindole analogue. Molecules 2006, 11, 700-706. (Pubitemid 44492708)
    • (2006) Molecules , vol.11 , Issue.9 , pp. 700-706
    • Teng, D.1    Zhang, H.2    Mendonca, A.3
  • 29
    • 33746297623 scopus 로고    scopus 로고
    • Highly diastereoselective one-pot synthesis of spirocyclic oxindoles through intramolecular Ullmann coupling and Claisen rearrangement
    • DOI 10.1002/anie.200504247
    • Miyamoto, H.; Okawa, Y.; Nakazaki, A.; Kobayashi, S. Highly diastereoselective one-pot synthesis of spirocyclic oxindoles through intramolecular Ullmann coupling and Claisen rearrangement. Angew. Chem. Int. Ed. 2006, 45, 2274-2277. (Pubitemid 44105161)
    • (2006) Angewandte Chemie - International Edition , vol.45 , Issue.14 , pp. 2274-2277
    • Miyamoto, H.1    Okawa, Y.2    Nakazaki, A.3    Kobayashi, S.4
  • 30
    • 33846430515 scopus 로고    scopus 로고
    • Simple and one-pot protocol for synthesis of indene-spiro-oxindoles involving tandem Prins and Friedel-Crafts reactions
    • Basavaiah, D.; Reddy, K. R. Simple and one-pot protocol for synthesis of indene-spiro-oxindoles involving tandem Prins and Friedel-Crafts reactions. Org. Lett. 2007, 9, 57-60.
    • (2007) Org. Lett. , vol.9 , pp. 57-60
    • Basavaiah, D.1    Reddy, K.R.2
  • 31
    • 70349784950 scopus 로고    scopus 로고
    • Targeting structural and stereochemical complexity by organocascade catalysis: Construction of spirocyclic oxindoles having multiple stereocenters
    • Bencivenni, G.; Wu, L. Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M. P.; Bartoli, G.; Melchiorre, P. Targeting structural and stereochemical complexity by organocascade catalysis: Construction of spirocyclic oxindoles having multiple stereocenters. Angew. Chem. Int. Ed. 2009, 48, 7200-7203.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7200-7203
    • Bencivenni, G.1    Wu, L.Y.2    Mazzanti, A.3    Giannichi, B.4    Pesciaioli, F.5    Song, M.P.6    Bartoli, G.7    Melchiorre, P.8
  • 32
    • 77952712196 scopus 로고    scopus 로고
    • An efficient one-pot synthesis of novel pyrazolophthalazinyl spirooxindoles
    • Shanthi, G.; Perumal, P. T. An efficient one-pot synthesis of novel pyrazolophthalazinyl spirooxindoles. J. Chem. Sci. 2010, 122, 415-421.
    • (2010) J. Chem. Sci. , vol.122 , pp. 415-421
    • Shanthi, G.1    Perumal, P.T.2
  • 33
    • 76649091565 scopus 로고    scopus 로고
    • Chemistry of andrographolide: Formation of novel di-spiropyrrolidino and di-spiropyrrolizidino-oxindole adducts via one-pot three-component [3+2] azomethine ylide cycloaddition
    • Hazra, A.; Paira, P.; Sahu, K. B.; Naskar, S.; Saha, P.; Paira, R.; Mondal, S.; Maity, A.; Luger, P.; Weber, M.; Mondal, N. B.; Banerjee, S. Chemistry of andrographolide: formation of novel di-spiropyrrolidino and di-spiropyrrolizidino-oxindole adducts via one-pot three-component [3+2] azomethine ylide cycloaddition. Tetrahedron Lett. 2010, 51, 1585-1588.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 1585-1588
    • Hazra, A.1    Paira, P.2    Sahu, K.B.3    Naskar, S.4    Saha, P.5    Paira, R.6    Mondal, S.7    Maity, A.8    Luger, P.9    Weber, M.10    Mondal, N.B.11    Banerjee, S.12
  • 34
    • 33745243766 scopus 로고    scopus 로고
    • 1,3-Dipolar cycloaddition of azomethine ylides generated from aziridines in supercritical carbon dioxide
    • DOI 10.1016/j.tetlet.2006.05.179, PII S0040403906011348
    • Gomes, P. J. S.; Nunes, C. M.; Pais, A. A. C. C.; Pinho e Melo, T. M. V. D.; Arnaut, L. G. 1, 3-Dipolar cycloaddition of azomethine ylides generated from aziridines in supercritical carbon dioxide. Tetrahedron Lett. 2006, 47, 5475-5479. (Pubitemid 43929026)
    • (2006) Tetrahedron Letters , vol.47 , Issue.31 , pp. 5475-5479
    • Gomes, P.J.S.1    Nunes, C.M.2    Pais, A.A.C.C.3    Pinhoe Melo, T.M.V.D.4    Arnaut, L.G.5
  • 35
    • 33748685012 scopus 로고    scopus 로고
    • X{double bond, long}Y-ZH compounds as potential 1,3-dipoles. Part 63: Silver catalysed azomethine ylide cycloaddition-the synthesis of spiro homoserine lactone analogues
    • DOI 10.1016/j.tet.2006.08.077, PII S0040402006013792
    • Grigg, R.; Sarker, M. A. B. XY-ZH compounds as potential 1, 3-dipoles. Part 63: Silver catalysed azomethine ylide cycloaddition-the synthesis of spiro homoserine lactone analogues. Tetrahedron 2006, 62, 10332-10343. (Pubitemid 44397125)
    • (2006) Tetrahedron , vol.62 , Issue.44 , pp. 10332-10343
    • Grigg, R.1    Sarker, M.A.B.2
  • 36
    • 0035925104 scopus 로고    scopus 로고
    • Polyhydroxylated alkaloids - Natural occurrence and therapeutic applications
    • DOI 10.1016/S0031-9422(00)00451-9, PII S0031942200004519
    • Watson, A. A.; Fleet, G. W. J.; Asano, N.; Molyneux, R. J.; Nash, R. J. Polyhydroxylated alkaloidsnatural occurrence and therapeutic applications. Phytochemistry 2001, 56, 265-295. (Pubitemid 32162799)
    • (2001) Phytochemistry , vol.56 , Issue.3 , pp. 265-295
    • Watson, A.A.1    Fleet, G.W.J.2    Asano, N.3    Molyneux, R.J.4    Nash, R.J.5
  • 37
    • 35548973101 scopus 로고    scopus 로고
    • Synthesis of novel functionalized 3-spiropyrrolizidine and 3-spiropyrrolidine oxindoles from Baylis-Hillman adducts of isatin and heteroaldehydes with azomethine ylides via [3+2] cycloaddition
    • Shanmugam, P.; Viswambharan, B.; Madhavan, S. Synthesis of novel functionalized 3-spiropyrrolizidine and 3-spiropyrrolidine oxindoles from Baylis-Hillman adducts of isatin and heteroaldehydes with azomethine ylides via [3+2] cycloaddition. Org. Lett. 2007, 9, 4095-4098.
    • (2007) Org. Lett. , vol.9 , pp. 4095-4098
    • Shanmugam, P.1    Viswambharan, B.2    Madhavan, S.3
  • 38
    • 70350676939 scopus 로고    scopus 로고
    • Highly enantioselective catalytic 1, 3-dipolar cycloaddition involving 2, 3-allenoate dipolarophiles
    • Yu, J.; He, L.; Chen, X. H.; Song, J.; Chen, W. J.; Gong, L. Z. Highly enantioselective catalytic 1, 3-dipolar cycloaddition involving 2, 3-allenoate dipolarophiles. Org. Lett. 2009, 11, 4946-4949.
    • (2009) Org. Lett. , vol.11 , pp. 4946-4949
    • Yu, J.1    He, L.2    Chen, X.H.3    Song, J.4    Chen, W.J.5    Gong, L.Z.6
  • 39
    • 79955604603 scopus 로고    scopus 로고
    • Asymmetic organocatalytic 1, 3-dipolar cycloaddition of azomethine ylide to methyl 2-(2-nitrophenyl) acrylate for the synthesis of diastereoisomers of spirotryprostatin A
    • Cheng. M. N.; Wang, H.; Gong, L. Z. Asymmetic organocatalytic 1, 3-dipolar cycloaddition of azomethine ylide to methyl 2-(2-nitrophenyl) acrylate for the synthesis of diastereoisomers of spirotryprostatin A. Org. Lett. 2011, 13, 2418-2421.
    • (2011) Org. Lett. , vol.13 , pp. 2418-2421
    • Cheng, M.N.1    Wang, H.2    Gong, L.Z.3
  • 40
    • 0031434404 scopus 로고    scopus 로고
    • Indolizidine and quinolizidine alkaloids
    • Michael, J. P. Indolizidine and quinolizidine alkaloids. Nat. Prod. Rep. 1997, 14, 619-636. (Pubitemid 28010215)
    • (1997) Natural Product Reports , vol.14 , Issue.6 , pp. 619-636
    • Michael, J.P.1
  • 41
    • 0032143883 scopus 로고    scopus 로고
    • Pyrrolizidine alkaloids
    • Liddell, J. R. Pyrrolizidine alkaloids. Nat. Prod. Rep. 1998, 15, 363-370. (Pubitemid 28397879)
    • (1998) Natural Product Reports , vol.15 , Issue.4 , pp. 363-370
    • Liddell, J.R.1
  • 42
    • 0842284205 scopus 로고    scopus 로고
    • The three-component reaction between isatin, α-amino acids, and dipolarophiles
    • Rehn, S.; Bergman, J.; Stensland, B. The three-component reaction between isatin, α-amino acids, and dipolarophiles. Eur. J. Org. Chem. 2004, 2004, 413-418.
    • (2004) Eur. J. Org. Chem. , vol.2004 , pp. 413-418
    • Rehn, S.1    Bergman, J.2    Stensland, B.3
  • 43
    • 77955715841 scopus 로고    scopus 로고
    • Highly regioselective synthesis of glycospiro heterocycles through 1, 3-dipolar cycloaddition reaction
    • Prasanna, R.; Purushothaman, S.; Raghunathan, R. Highly regioselective synthesis of glycospiro heterocycles through 1, 3-dipolar cycloaddition reaction. Tetrahedron Lett. 2010, 51, 4538-4542.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 4538-4542
    • Prasanna, R.1    Purushothaman, S.2    Raghunathan, R.3
  • 44
    • 80054952801 scopus 로고    scopus 로고
    • Crystallographic data of 4a reported in this manuscript have been deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-828257. Copies of the data can be obtained free of charge via, or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk
    • Crystallographic data of 4a reported in this manuscript have been deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-828257. Copies of the data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.