메뉴 건너뛰기




Volumn 45, Issue 2, 2010, Pages 846-848

Asymmetric synthesis of anticancer β-lactams via Staudinger reaction: Utilization of chiral ketene from carbohydrate

Author keywords

Lactams; Anticancer agents; Asymmetric synthesis; Carbohydrate; In vitro tests; Staudinger reaction

Indexed keywords

ANTINEOPLASTIC AGENT; BETA LACTAM DERIVATIVE; CARBOHYDRATE; KETENE DERIVATIVE;

EID: 73549100633     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.11.024     Document Type: Article
Times cited : (94)

References (32)
  • 1
    • 0032489812 scopus 로고    scopus 로고
    • Targeted delivery of chemotherapeutics: tumor-activated prodrug therapy
    • For an example, see:
    • For an example, see:. Chari R.V.J. Targeted delivery of chemotherapeutics: tumor-activated prodrug therapy. Adv. Drug Deliv. Rev. 31 (1998) 89-104
    • (1998) Adv. Drug Deliv. Rev. , vol.31 , pp. 89-104
    • Chari, R.V.J.1
  • 2
    • 0034405709 scopus 로고    scopus 로고
    • Indium-mediated facile synthesis of 3-unsubstituted ferrocenyl β-lactams
    • Ghatak A., Becker F.F., and Banik B.K. Indium-mediated facile synthesis of 3-unsubstituted ferrocenyl β-lactams. Heterocycles 53 (2000) 2769-2773
    • (2000) Heterocycles , vol.53 , pp. 2769-2773
    • Ghatak, A.1    Becker, F.F.2    Banik, B.K.3
  • 3
    • 0034698449 scopus 로고    scopus 로고
    • Indium-mediated facile synthesis of 3-unsubstituted β-lactams
    • Banik B.K., Ghatak A., and Becker F.F. Indium-mediated facile synthesis of 3-unsubstituted β-lactams. J. Chem. Soc. Perkin Trans. 1 (2000) 2179-2181
    • (2000) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 2179-2181
    • Banik, B.K.1    Ghatak, A.2    Becker, F.F.3
  • 4
    • 0034686858 scopus 로고    scopus 로고
    • Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines
    • Banik B.K., and Becker F.F. Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines. Tetrahedron Lett. 41 (2000) 6551-6554
    • (2000) Tetrahedron Lett. , vol.41 , pp. 6551-6554
    • Banik, B.K.1    Becker, F.F.2
  • 5
    • 0035746425 scopus 로고    scopus 로고
    • Synthesis of tricyclic β-lactams via palladium acetate-induced Heck reaction
    • Ng S., Banik I., Okawa A., Becker F.F., and Banik B.K. Synthesis of tricyclic β-lactams via palladium acetate-induced Heck reaction. J. Chem. Res. (2001) 118-119
    • (2001) J. Chem. Res. , pp. 118-119
    • Ng, S.1    Banik, I.2    Okawa, A.3    Becker, F.F.4    Banik, B.K.5
  • 6
    • 0037121595 scopus 로고    scopus 로고
    • A new entry to N-unsubstituted β-lactams through a solid-phase approach
    • Dasgupta S.K., and Banik B.K. A new entry to N-unsubstituted β-lactams through a solid-phase approach. Tetrahedron Lett. 43 (2002) 445-9447
    • (2002) Tetrahedron Lett. , vol.43 , pp. 445-9447
    • Dasgupta, S.K.1    Banik, B.K.2
  • 7
    • 0037450457 scopus 로고    scopus 로고
    • A facile synthesis of oxazines by indium-induced reduction-rearrangement of the nitro β-lactams
    • Banik B.K., Samajdar S., and Banik I. A facile synthesis of oxazines by indium-induced reduction-rearrangement of the nitro β-lactams. Tetrahedron Lett. 44 (2003) 1699-1701
    • (2003) Tetrahedron Lett. , vol.44 , pp. 1699-1701
    • Banik, B.K.1    Samajdar, S.2    Banik, I.3
  • 8
    • 0037344467 scopus 로고    scopus 로고
    • Cycloaddition of naphthalenyl and anthracenyl imines: interesting aspects of the Staudinger reaction
    • Banik B.K., Banik I., and Hackfeld L. Cycloaddition of naphthalenyl and anthracenyl imines: interesting aspects of the Staudinger reaction. Heterocycles 59 (2003) 505-508
    • (2003) Heterocycles , vol.59 , pp. 505-508
    • Banik, B.K.1    Banik, I.2    Hackfeld, L.3
  • 9
    • 0032553002 scopus 로고    scopus 로고
    • Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of some chrysene derivatives
    • Becker F.F., and Banik B.K. Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of some chrysene derivatives. Bioorg. Med. Chem. Lett. 8 (1998) 2877-2880
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2877-2880
    • Becker, F.F.1    Banik, B.K.2
  • 10
    • 0033761583 scopus 로고    scopus 로고
    • Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of dibenzofluorene derivatives
    • Becker F.F., Mukhopadhyay C., Hackfeld L., Banik I., and Banik B.K. Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of dibenzofluorene derivatives. Bioorg. Med. Chem. 8 (2000) 2693-2699
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 2693-2699
    • Becker, F.F.1    Mukhopadhyay, C.2    Hackfeld, L.3    Banik, I.4    Banik, B.K.5
  • 11
    • 0035108369 scopus 로고    scopus 로고
    • Polycyclic aromatic compounds as anticancer agents: structure-activity relationships of chrysene and pyrene derivatives
    • Banik B.K., and Becker F.F. Polycyclic aromatic compounds as anticancer agents: structure-activity relationships of chrysene and pyrene derivatives. Bioorg. Med. Chem. 9 (2000) 593-605
    • (2000) Bioorg. Med. Chem. , vol.9 , pp. 593-605
    • Banik, B.K.1    Becker, F.F.2
  • 12
    • 0034827198 scopus 로고    scopus 로고
    • Synthesis electrophilic substitution and structure-activity relationship studies of polycyclic aromatic compounds towards the development of anticancer agents
    • Banik B.K., and Becker F.F. Synthesis electrophilic substitution and structure-activity relationship studies of polycyclic aromatic compounds towards the development of anticancer agents. Curr. Med. Chem. 8 (2001) 1513-1533
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1513-1533
    • Banik, B.K.1    Becker, F.F.2
  • 13
    • 2142678851 scopus 로고    scopus 로고
    • Current approaches to the development of new chemotherapeutic anticancer agents
    • Banik B.K. Current approaches to the development of new chemotherapeutic anticancer agents. Curr. Med. Chem. 8 (2001) 1343
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1343
    • Banik, B.K.1
  • 14
    • 0037413527 scopus 로고    scopus 로고
    • Stereoselective synthesis of β-lactams with polyaromatic imines: entry to new and novel anticancer agents
    • Banik I., Becker F.F., and Banik B.K. Stereoselective synthesis of β-lactams with polyaromatic imines: entry to new and novel anticancer agents. J. Med. Chem. 46 (2003) 12-15
    • (2003) J. Med. Chem. , vol.46 , pp. 12-15
    • Banik, I.1    Becker, F.F.2    Banik, B.K.3
  • 15
    • 2142824194 scopus 로고    scopus 로고
    • Synthesis of anticancer β-lactams: mechanism of action
    • Banik B.K., Becker F.F., and Banik I. Synthesis of anticancer β-lactams: mechanism of action. Bioorg. Med. Chem. 12 (2004) 2523-2528
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 2523-2528
    • Banik, B.K.1    Becker, F.F.2    Banik, I.3
  • 16
    • 18144387622 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction
    • Banik B.K., Banik I., and Becker F.F. Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction. Bioorg. Med. Chem. 13 (2005) 3611-3622
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 3611-3622
    • Banik, B.K.1    Banik, I.2    Becker, F.F.3
  • 17
    • 0037068452 scopus 로고    scopus 로고
    • Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase
    • Hernandez A.I., Balzarini J., Karlsson A., Camarasa M.J., and Perez M.J. Acyclic nucleoside analogues as novel inhibitors of human mitochondrial thymidine kinase. J. Med. Chem. 45 (2002) 4254-4263
    • (2002) J. Med. Chem. , vol.45 , pp. 4254-4263
    • Hernandez, A.I.1    Balzarini, J.2    Karlsson, A.3    Camarasa, M.J.4    Perez, M.J.5
  • 19
    • 0037194644 scopus 로고    scopus 로고
    • Conformationally constrained nicotines: polycyclic, bridged, and spiro-annulated analogues as novel ligands for the nicotinic acetylcholine receptor
    • Ullrich T., Krich S., Binder D., Mereiter K., Anderson D.J., Meyer M.D., and Pyerin M. Conformationally constrained nicotines: polycyclic, bridged, and spiro-annulated analogues as novel ligands for the nicotinic acetylcholine receptor. J. Med. Chem. 45 (2002) 4047-4054
    • (2002) J. Med. Chem. , vol.45 , pp. 4047-4054
    • Ullrich, T.1    Krich, S.2    Binder, D.3    Mereiter, K.4    Anderson, D.J.5    Meyer, M.D.6    Pyerin, M.7
  • 22
    • 0029965801 scopus 로고    scopus 로고
    • An efficient synthesis of cis-3-hydroxy-4-phenyl-β-lactams: precursor for taxol side chain
    • For the symmetric synthesis of optically active hydroxy β-lactams from chiral ketenes following Staudinger reaction, see:
    • For the symmetric synthesis of optically active hydroxy β-lactams from chiral ketenes following Staudinger reaction, see:. Srirajan V., Deshmukh A.R.A.S., and Bhawal B.M. An efficient synthesis of cis-3-hydroxy-4-phenyl-β-lactams: precursor for taxol side chain. Tetrahedron 52 (1996) 5585-5590
    • (1996) Tetrahedron , vol.52 , pp. 5585-5590
    • Srirajan, V.1    Deshmukh, A.R.A.S.2    Bhawal, B.M.3
  • 23
    • 0037458535 scopus 로고    scopus 로고
    • Ephedrine derived reusable chiral auxiliary for the synthesis of optically pure 3-hydroxy-4-aryl-β-lactams
    • Shinkre B.A., Puranik V.G., Bhawal B.M., and Deshmukh A.R.A.S. Ephedrine derived reusable chiral auxiliary for the synthesis of optically pure 3-hydroxy-4-aryl-β-lactams. Tetrahedron: Asymmetry 14 (2003) 453-459
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 453-459
    • Shinkre, B.A.1    Puranik, V.G.2    Bhawal, B.M.3    Deshmukh, A.R.A.S.4
  • 24
    • 33947218419 scopus 로고    scopus 로고
    • Asymmetric synthesis of β-lactams by [2 + 2] cycloaddition using 1,4:3,6-dianhydro-d-glucitol (isosorbide) derived chiral pools
    • Shaikah A.L., Kale A.S., Shaikh M.A., Puranik V.G., and Deshmukh A.R.A.S. Asymmetric synthesis of β-lactams by [2 + 2] cycloaddition using 1,4:3,6-dianhydro-d-glucitol (isosorbide) derived chiral pools. Tetrahedron 63 (2007) 3380-3388
    • (2007) Tetrahedron , vol.63 , pp. 3380-3388
    • Shaikah, A.L.1    Kale, A.S.2    Shaikh, M.A.3    Puranik, V.G.4    Deshmukh, A.R.A.S.5
  • 25
    • 0025978010 scopus 로고
    • An asymmetric synthesis of a 3-hydroxy-β-lactam by ketene-imine cycloaddition: utilization of chiral ketenes from carbohydrates
    • Borer B.C., and Balogh D.W. An asymmetric synthesis of a 3-hydroxy-β-lactam by ketene-imine cycloaddition: utilization of chiral ketenes from carbohydrates. Tetrahedron Lett. 32 (1991) 1039-1040
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1039-1040
    • Borer, B.C.1    Balogh, D.W.2
  • 26
    • 34250809033 scopus 로고    scopus 로고
    • On the stereodivergent behavior observed in the Staudinger reaction between methoxyketene and (E)-N-benzylidenearyl amines
    • Banik B.K., Lecea A., Arrieta A., Cozar A., and Cossio F.P. On the stereodivergent behavior observed in the Staudinger reaction between methoxyketene and (E)-N-benzylidenearyl amines. Angew. Chem. Int. Ed. 46 (2007) 3028-3032
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3028-3032
    • Banik, B.K.1    Lecea, A.2    Arrieta, A.3    Cozar, A.4    Cossio, F.P.5
  • 27
    • 0033525683 scopus 로고    scopus 로고
    • A convenient trans-stereoselective synthesis of phenanthridine derived 2-azetidinones using the Staudinger ketene-imine cycloaddition
    • For the preparation of trans β-lactams using different strategies, see:
    • For the preparation of trans β-lactams using different strategies, see:. Alcaide B., and Vicente-Rodriguez A. A convenient trans-stereoselective synthesis of phenanthridine derived 2-azetidinones using the Staudinger ketene-imine cycloaddition. Tetrahedron Lett. 40 (1999) 2005-2006
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2005-2006
    • Alcaide, B.1    Vicente-Rodriguez, A.2
  • 28
    • 0032497605 scopus 로고    scopus 로고
    • Beta-lactams derived from the reaction of phenanthridines and 11 H-dibenzo[b,e]azepin-11-one with phenylvaleryl chloride synthesis of fused analogs of the cholesterol absorption inhibitor Sch 48461
    • Afonso A., Rosenblum S.B., Puar M.S., and McPhail A.T. Beta-lactams derived from the reaction of phenanthridines and 11 H-dibenzo[b,e]azepin-11-one with phenylvaleryl chloride synthesis of fused analogs of the cholesterol absorption inhibitor Sch 48461. Tetrahedron Lett. 39 (1998) 7431-7434
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7431-7434
    • Afonso, A.1    Rosenblum, S.B.2    Puar, M.S.3    McPhail, A.T.4
  • 29
    • 0027761171 scopus 로고
    • Synthesis of trans-1- p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one. A key starting β-lactam for 2′-epi-taxol
    • Endo M., and Droghini R. Synthesis of trans-1- p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one. A key starting β-lactam for 2′-epi-taxol. Bioorg. Med. Chem. Lett. 3 (1993) 2483-2486
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 2483-2486
    • Endo, M.1    Droghini, R.2
  • 30
    • 0028891310 scopus 로고
    • Stereocontrol of β-lactam formation using microwave irradiation
    • Bose A.K., Banik B.K., and Manhas M.S. Stereocontrol of β-lactam formation using microwave irradiation. Tetrahedron Lett. 36 (1995) 213-216
    • (1995) Tetrahedron Lett. , vol.36 , pp. 213-216
    • Bose, A.K.1    Banik, B.K.2    Manhas, M.S.3
  • 31
    • 0030834192 scopus 로고    scopus 로고
    • Enantiopure α-hydroxy-β-lactams via stereoselective glycosylation
    • Banik B.K., Manhas M.S., and Bose A.K. Enantiopure α-hydroxy-β-lactams via stereoselective glycosylation. Tetrahedron Lett. 38 (1997) 5077-5080
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5077-5080
    • Banik, B.K.1    Manhas, M.S.2    Bose, A.K.3
  • 32
    • 73549088562 scopus 로고    scopus 로고
    • note
    • 3) δ (ppm): 20.72, 21.10, 22.64, 23.68, 62.61, 63.23, 65.09, 66.74, 85.93, 97.61, 115.11, 120. 90, 122.87, 123.60, 124.52, 126.68, 126.73, 126.76, 126.88, 127.03, 127.39, 127.56, 128.93, 129.16, 130.05, 131.17, 132.22, 136.16, 165.54, 169.94, 170.78.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.