Main Article Content
Abstract
Microwave-mediated optically active O-glycosides of anticancer β-lactams is synthesized by cycloaddition reaction of an activated carbohydrate acid with an imine. The stereochemistry differences of the products under microwave-induced reaction and classical method is not significant in contrast to other known available methods.
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Article Details
References
- L. Formigli, L. Papucci, A. Tani, N. Schiavone, A. Tempestini, G.E. Orlandini, S. Capaccioli and S. Zecchi Orlandini, Aponecrosis: Morphological and Biochemical Exploration of a Syncretic Process of Cell Death Sharing Apoptosis and Necrosis, J. Cell. Physiol., 182, 41 (2000); https://doi.org/10.1002/(SICI)1097-4652(200001)182:1<41::AID-JCP5>3.0.CO;2-7.
- S. Sperandio, I. de Belle and D.E. Bredesen, An Alternative, Nonapopto-tic form of Programmed Cell Death, Proc. Natl. Acad. Sci. USA, 97, 14376 (2000); https://doi.org/10.1073/pnas.97.26.14376.
- B.K. Banik, F.F. Becker and I. Banik, Synthesis of Anticancer b-Lactams: Mechanism of Action, Bioorg. Med. Chem., 12, 2523 (2004); https://doi.org/10.1016/j.bmc.2004.03.033.
- B.K. Banik, Heterocyclic Scaffolds I, Topics In: Heterocyclic Chemistry, Springer, vol. 22, pp 1-379 (2010).
- B.K. Banik, b-Lactams: Synthesis and Biological Evaluation, Topics In: Heterocyclic Chemistry, Springer, vol. 30, pp 1-226 (2012).
- B.K. Banik, b-Lactam Chemistry, Tetrahedron Symposium-in-Print, 68, 10627-10834 (2012); https://doi.org/10.1016/S0040-4020(12)01701-2.
- I. Banik and B.K. Banik, Microwave-Induced Chemical Manipulation of b-Lactam, Springer, vol. 88, pp. 781-1007 (2012).
- B.K. Banik, Beta Lactams: Novel Synthetic Pathways and Applications, Springer, pp. 1-419 (2017).
- P.T. Parvatkar, P.S. Parameswaran and B.K. Banik, ed.: B.K. Banik, Solid Phase Synthesis of b-Lactams: Results and Scope, In: Beta Lactams: Novel Synthetic Pathways and Applications, Spinger, pp. 253-284 (2017).
- S. Basu and B.K. Banik, ed.: B.K. Banik, Beta Lactams as Clinically Active Molecules, In: Beta Lactams: Novel Synthetic Pathways and Appli-cations, Springer, pp. 285-310 (2017).
- B.K. Banik, Synthesis and Biological Studies of Novel b-Lactams, CRC Book, pp. 31-72 (2013).
- I. Banik, F.F. Becker and B.K. Banik, Stereoselective Synthesis of b-Lactams with Polyaromatic Imines: Entry to New and Novel Anticancer Agents, J. Med. Chem., 46, 12 (2003); https://doi.org/10.1021/jm0255825.
- B.K. Banik, Curr. Med. Chem., 11, (2004); https://doi.org/10.2174/0929867043364892.
- B.K. Banik, I. Banik and F.F. Becker, Stereocontrolled Synthesis of Anti-cancer b-Lactams via the Staudinger Reaction, Bioorg. Med. Chem., 13, 3611 (2005); https://doi.org/10.1016/j.bmc.2005.03.044.
- B.K. Banik and F.F. Becker, Selective Anticancer Activity of b-Lactams Derived from Polyaromatic Compound, Mol. Med. Rep., 3, 315 (2010); https://doi.org/10.3892/mmr_000000257.
- B.K. Banik, I. Banik and F.F. Becker, ed.: B. Banik, Novel Anticancer b-Lactams. Heterocyclic Scaffolds I. Topics in Heterocyclic Chemistry, Springer, Berlin, Heidelberg, vol. vol 22, pp. 349-373 (2010); https://doi.org/10.1007/7081_2010_28.
- B.K. Banik, I. Banik and F.F. Becker, Asymmetric Synthesis of Anti-cancer b-Lactams via Staudinger Reaction: Utilization of Chiral Ketene from Carbohydrate, Eur. J. Med. Chem., 45, 846 (2010); https://doi.org/10.1016/j.ejmech.2009.11.024.
- B.K. Banik, S. Samajdar and F.F. Becker, Asymmetric Synthesis of Anticancer b-Lactams via Staudinger Reaction, Mol. Med. Rep., 3, 319 (2010); https://doi.org/10.3892/mmr_000000259.
- B.K. Banik, Curing Cancer through Manipulation of Molecules, Int. Innov., 50-53 (2011).
- B.K. Banik, M.S. Manhas and A.K. Bose, Studies on Lactams: 89. Versatile, b-Lactam Synthons: Enantiospecific Synthesis of (-)-Polyoxamic Acid, J. Org. Chem., 58, 307 (1993); https://doi.org/10.1021/jo00054a007.
- B.K. Banik, M.S. Manhas and A.K. Bose, Stereospecific Glycosylation via Ferrier Rearrangement for Optical Resolution, J. Org. Chem., 59, 4714 (1994); https://doi.org/10.1021/jo00096a004.
- B.K. Banik, M.S. Manhas and A.K. Bose, Enantiopure Hydroxy b-Lactams via Glycosylation, Tetrahedron Lett., 38, 5077 (1997); https://doi.org/10.1016/S0040-4039(97)01130-1.
- A.K. Bose, B.K. Banik, C. Mathur, D.R. Wagle and M.S. Manhas, Poly-hydroxy Amino Acid Derivatives via b-Lactams using Enantiospecific Approaches and Microwave Techniques, Tetrahedron, 56, 5603 (2000); https://doi.org/10.1016/S0040-4020(00)00410-5.
- A.L. Shaikh, O. Esparza and B.K. Banik, An Efficient Synthesis of Optically Active trans-(3R,4R)-3-acetoxy-4-aryl-1-(chrysen-6-yl)-azetidin-2-ones using (+)-Car-3-ene as a Chiral Auxiliary, Helv. Chim. Acta, 94, 2188 (2011); https://doi.org/10.1002/hlca.201100225.
- B.K. Banik, M.S. Manhas, Z. Kaluza, K.J. Barakat and A.K. Bose, Micro-wave-Induced Organic Reaction Enhancement Chemistry:4 Convenient Synthesis of Enantiopure a-Hydroxy-b-Lactams, Tetrahedron Lett., 33, 3603 (1992); https://doi.org/10.1016/S0040-4039(00)92513-9.
- A.K. Bose, B.K. Banik, K.J. Barakat and M.S. Manhas, Simplified Rapid Hydrogenation Under Microwave Irradiation: Selective Transformations of b-Lactams, Synlett, 575 (1993); https://doi.org/10.1055/s-1993-22534.
- B.K. Banik, K.J. Barakat, D.R. Wagle, M.S. Manhas and A.K. Bose, Microwave-Assisted Rapid and Simplified Hydrogenation, J. Org. Chem., 64, 5746 (1999); https://doi.org/10.1021/jo981516s.
- A.K. Bose, B.K. Banik and M.S. Manhas, Stereocontrol of b-Lactam Formation using Microwave Irradiation, Tetrahedron Lett., 36, 213 (1995); https://doi.org/10.1016/0040-4039(94)02225-Z.
- B.K. Banik, H. Aguilar and D. Cordova, Unprecedented Stereocontrol of b-Lactam Formation Derived from N-Cinnamylidenearylamine, Heterocycles, 71, 2321 (2007); https://doi.org/10.3987/COM-07-11134.
- H. Aguilar and B.K. Banik, Stereoselctivity of 3,3-Disubstituted b-Lactam Formation via Staudinger Reaction, Heterocycl. Commun., 15, 365 (2009); https://doi.org/10.1515/HC.2009.15.5.365.
- D. Bandyopadhyay and B.K. Banik, Microwave-Induced Stereocontrol of b-Lactam Formation with an N-Benzylidene-9,10-dihydrophenan-thren-3-amine via Staudinger Cycloaddition, Helv. Chim. Acta, 93, 298 (2010); https://doi.org/10.1002/hlca.200900212.
- R. Rodriguez and B.K. Banik, Diasteroselectivity in b-Lactam Form-ation with Conjugated Imines, Heterocycl. Lett., 1, 31 (2011).
- I. Banik, F.F. Backer and B.K. Banik, Microwave-Induced Stereo-specific Synthesis of b-Lactams Derived from Polyaromatic Imines: Influence of Multicyclic Rings at the Nitrogen, Heterocycl. Lett., 1, 55 (2011).
- D. Bandyopadhyay, M. Yanez and B.K. Banik, Microwave-Induced Stereoselectivity of b-Lactam Formation, Effects of Solvents, Heterocycl. Lett., 1, 65 (2011).
- B.K. Banik, B. Lecea, A. Arrieta, A. de Cózar and F.P. Cossío, On the Stereodivergent Behavior Observed in the Staudinger Reaction between Methoxyketene and (E)-N-Benzylidenearyl Amines, Angew. Chem. Int. Ed., 46, 3028 (2007); https://doi.org/10.1002/anie.200605231.
- B.C. Borer and D.W. Balogh, An Asymmetric Synthesis of a 3-Hydroxy-b-Lactam By Ketene-Imine Cycloaddition: Utilization of Chiral Ketenes from Carbohydrates, Tetrahedron Lett., 32, 1039 (1991); https://doi.org/10.1016/S0040-4039(00)74481-9.
References
L. Formigli, L. Papucci, A. Tani, N. Schiavone, A. Tempestini, G.E. Orlandini, S. Capaccioli and S. Zecchi Orlandini, Aponecrosis: Morphological and Biochemical Exploration of a Syncretic Process of Cell Death Sharing Apoptosis and Necrosis, J. Cell. Physiol., 182, 41 (2000); https://doi.org/10.1002/(SICI)1097-4652(200001)182:1<41::AID-JCP5>3.0.CO;2-7.
S. Sperandio, I. de Belle and D.E. Bredesen, An Alternative, Nonapopto-tic form of Programmed Cell Death, Proc. Natl. Acad. Sci. USA, 97, 14376 (2000); https://doi.org/10.1073/pnas.97.26.14376.
B.K. Banik, F.F. Becker and I. Banik, Synthesis of Anticancer b-Lactams: Mechanism of Action, Bioorg. Med. Chem., 12, 2523 (2004); https://doi.org/10.1016/j.bmc.2004.03.033.
B.K. Banik, Heterocyclic Scaffolds I, Topics In: Heterocyclic Chemistry, Springer, vol. 22, pp 1-379 (2010).
B.K. Banik, b-Lactams: Synthesis and Biological Evaluation, Topics In: Heterocyclic Chemistry, Springer, vol. 30, pp 1-226 (2012).
B.K. Banik, b-Lactam Chemistry, Tetrahedron Symposium-in-Print, 68, 10627-10834 (2012); https://doi.org/10.1016/S0040-4020(12)01701-2.
I. Banik and B.K. Banik, Microwave-Induced Chemical Manipulation of b-Lactam, Springer, vol. 88, pp. 781-1007 (2012).
B.K. Banik, Beta Lactams: Novel Synthetic Pathways and Applications, Springer, pp. 1-419 (2017).
P.T. Parvatkar, P.S. Parameswaran and B.K. Banik, ed.: B.K. Banik, Solid Phase Synthesis of b-Lactams: Results and Scope, In: Beta Lactams: Novel Synthetic Pathways and Applications, Spinger, pp. 253-284 (2017).
S. Basu and B.K. Banik, ed.: B.K. Banik, Beta Lactams as Clinically Active Molecules, In: Beta Lactams: Novel Synthetic Pathways and Appli-cations, Springer, pp. 285-310 (2017).
B.K. Banik, Synthesis and Biological Studies of Novel b-Lactams, CRC Book, pp. 31-72 (2013).
I. Banik, F.F. Becker and B.K. Banik, Stereoselective Synthesis of b-Lactams with Polyaromatic Imines: Entry to New and Novel Anticancer Agents, J. Med. Chem., 46, 12 (2003); https://doi.org/10.1021/jm0255825.
B.K. Banik, Curr. Med. Chem., 11, (2004); https://doi.org/10.2174/0929867043364892.
B.K. Banik, I. Banik and F.F. Becker, Stereocontrolled Synthesis of Anti-cancer b-Lactams via the Staudinger Reaction, Bioorg. Med. Chem., 13, 3611 (2005); https://doi.org/10.1016/j.bmc.2005.03.044.
B.K. Banik and F.F. Becker, Selective Anticancer Activity of b-Lactams Derived from Polyaromatic Compound, Mol. Med. Rep., 3, 315 (2010); https://doi.org/10.3892/mmr_000000257.
B.K. Banik, I. Banik and F.F. Becker, ed.: B. Banik, Novel Anticancer b-Lactams. Heterocyclic Scaffolds I. Topics in Heterocyclic Chemistry, Springer, Berlin, Heidelberg, vol. vol 22, pp. 349-373 (2010); https://doi.org/10.1007/7081_2010_28.
B.K. Banik, I. Banik and F.F. Becker, Asymmetric Synthesis of Anti-cancer b-Lactams via Staudinger Reaction: Utilization of Chiral Ketene from Carbohydrate, Eur. J. Med. Chem., 45, 846 (2010); https://doi.org/10.1016/j.ejmech.2009.11.024.
B.K. Banik, S. Samajdar and F.F. Becker, Asymmetric Synthesis of Anticancer b-Lactams via Staudinger Reaction, Mol. Med. Rep., 3, 319 (2010); https://doi.org/10.3892/mmr_000000259.
B.K. Banik, Curing Cancer through Manipulation of Molecules, Int. Innov., 50-53 (2011).
B.K. Banik, M.S. Manhas and A.K. Bose, Studies on Lactams: 89. Versatile, b-Lactam Synthons: Enantiospecific Synthesis of (-)-Polyoxamic Acid, J. Org. Chem., 58, 307 (1993); https://doi.org/10.1021/jo00054a007.
B.K. Banik, M.S. Manhas and A.K. Bose, Stereospecific Glycosylation via Ferrier Rearrangement for Optical Resolution, J. Org. Chem., 59, 4714 (1994); https://doi.org/10.1021/jo00096a004.
B.K. Banik, M.S. Manhas and A.K. Bose, Enantiopure Hydroxy b-Lactams via Glycosylation, Tetrahedron Lett., 38, 5077 (1997); https://doi.org/10.1016/S0040-4039(97)01130-1.
A.K. Bose, B.K. Banik, C. Mathur, D.R. Wagle and M.S. Manhas, Poly-hydroxy Amino Acid Derivatives via b-Lactams using Enantiospecific Approaches and Microwave Techniques, Tetrahedron, 56, 5603 (2000); https://doi.org/10.1016/S0040-4020(00)00410-5.
A.L. Shaikh, O. Esparza and B.K. Banik, An Efficient Synthesis of Optically Active trans-(3R,4R)-3-acetoxy-4-aryl-1-(chrysen-6-yl)-azetidin-2-ones using (+)-Car-3-ene as a Chiral Auxiliary, Helv. Chim. Acta, 94, 2188 (2011); https://doi.org/10.1002/hlca.201100225.
B.K. Banik, M.S. Manhas, Z. Kaluza, K.J. Barakat and A.K. Bose, Micro-wave-Induced Organic Reaction Enhancement Chemistry:4 Convenient Synthesis of Enantiopure a-Hydroxy-b-Lactams, Tetrahedron Lett., 33, 3603 (1992); https://doi.org/10.1016/S0040-4039(00)92513-9.
A.K. Bose, B.K. Banik, K.J. Barakat and M.S. Manhas, Simplified Rapid Hydrogenation Under Microwave Irradiation: Selective Transformations of b-Lactams, Synlett, 575 (1993); https://doi.org/10.1055/s-1993-22534.
B.K. Banik, K.J. Barakat, D.R. Wagle, M.S. Manhas and A.K. Bose, Microwave-Assisted Rapid and Simplified Hydrogenation, J. Org. Chem., 64, 5746 (1999); https://doi.org/10.1021/jo981516s.
A.K. Bose, B.K. Banik and M.S. Manhas, Stereocontrol of b-Lactam Formation using Microwave Irradiation, Tetrahedron Lett., 36, 213 (1995); https://doi.org/10.1016/0040-4039(94)02225-Z.
B.K. Banik, H. Aguilar and D. Cordova, Unprecedented Stereocontrol of b-Lactam Formation Derived from N-Cinnamylidenearylamine, Heterocycles, 71, 2321 (2007); https://doi.org/10.3987/COM-07-11134.
H. Aguilar and B.K. Banik, Stereoselctivity of 3,3-Disubstituted b-Lactam Formation via Staudinger Reaction, Heterocycl. Commun., 15, 365 (2009); https://doi.org/10.1515/HC.2009.15.5.365.
D. Bandyopadhyay and B.K. Banik, Microwave-Induced Stereocontrol of b-Lactam Formation with an N-Benzylidene-9,10-dihydrophenan-thren-3-amine via Staudinger Cycloaddition, Helv. Chim. Acta, 93, 298 (2010); https://doi.org/10.1002/hlca.200900212.
R. Rodriguez and B.K. Banik, Diasteroselectivity in b-Lactam Form-ation with Conjugated Imines, Heterocycl. Lett., 1, 31 (2011).
I. Banik, F.F. Backer and B.K. Banik, Microwave-Induced Stereo-specific Synthesis of b-Lactams Derived from Polyaromatic Imines: Influence of Multicyclic Rings at the Nitrogen, Heterocycl. Lett., 1, 55 (2011).
D. Bandyopadhyay, M. Yanez and B.K. Banik, Microwave-Induced Stereoselectivity of b-Lactam Formation, Effects of Solvents, Heterocycl. Lett., 1, 65 (2011).
B.K. Banik, B. Lecea, A. Arrieta, A. de Cózar and F.P. Cossío, On the Stereodivergent Behavior Observed in the Staudinger Reaction between Methoxyketene and (E)-N-Benzylidenearyl Amines, Angew. Chem. Int. Ed., 46, 3028 (2007); https://doi.org/10.1002/anie.200605231.
B.C. Borer and D.W. Balogh, An Asymmetric Synthesis of a 3-Hydroxy-b-Lactam By Ketene-Imine Cycloaddition: Utilization of Chiral Ketenes from Carbohydrates, Tetrahedron Lett., 32, 1039 (1991); https://doi.org/10.1016/S0040-4039(00)74481-9.