Asymmetric synthesis of anticancer β-lactams via Staudinger reaction

Molecular Medicine Reports

Volumn 3, Issue 2, 2010, Pages 319-321

  Banik, Bimal K ^a   Samajdar, Susanta ^b   Becker, Frederick F ^b  

^a UNIVERSITY OF TEXAS PAN AMERICAN   (United States)

^b UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

lactams; Staudinger reaction

Indexed keywords

ANTINEOPLASTIC AGENT; BETA LACTAM DERIVATIVE; CHRYSENE DERIVATIVE; N (6 CHRYSENYL) 3 ACETOXY 4 PHENYL 2 AZETIDINE 2 ONE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ASYMMETRIC SYNTHESIS; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; STAUDINGER REACTION; STRUCTURE ACTIVITY RELATION;

EID: 77950843614     PISSN: 17912997     EISSN: 17913004     Source Type: Journal    
DOI: 10.3892/mmr-00000259     Document Type: Article

References (14)

1. Chari RVJ: Targeted delivery of chemotherapeutics: tumor-activated prodrug therapy. Adv Drug Delivery Rev 31: 89-104, 1998.
2. Banik BK, Samajdar S and Banik I: A facile synthesis of oxazines by indium-induced reduction-rearrangement of the nitro β-lactams. Tetrahedron Lett 44: 1699, 2003.
3. Banik BK, Banik I and Hackfeld L: Cycloaddition of naphthalenyl and anthracenyl imines: interesting aspects of the Staudinger reaction. Heterocycles 9: 505-508, 2003.
4. Banik BK and Becker FF: Polycyclic aromatic compounds as anticancer agents. Structure-activity relationships of chrysene and pyrene derivatives. Bioorg Med Chem 46: 593-605, 2001.
5. Banik I, Becker FF and Banik BK: Stereoselective synthesis of β-lactams with polyaromatic imines: entry to new and novel anticancer agents. J Med Chem 12: 12-15, 2003.
6. Banik BK, Becker FF and Banik I: Synthesis of anticancer β-lactams: mechanism of action. Bio Org Med Chem 13: 2523-2528, 2004.
7. Banik BK, Banik I and Becker FF: Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction. Bio Org Med Chem 13: 3611-3622, 2005.
8. Bose AK, Manhas MS, Banik BK and Srirajan V: β-Lactams: cyclic amides of distinction. In: Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry and Material Science. Greenberg A, Breneman CM and Liebman JF (eds). Wiley-Interscience, New York, pp157-214, 2000.
9. Borer BC and Balogh DW: An asymmetric synthesis of a 3-hydroxy-β- lactam by ketene-imine cycloaddition: utilization of chiral ketenes from carbohydrates. Tetrahedron Lett 32: 1039-1040, 1991.
10. Srirajain V, Deshmukh A and Bhawal BM: An efficient synthesis of cis-3-hydroxy-4-phenyl-β-lactams: precursor for taxol side chain. Tetrahedron 52: 5585-5590, 1996.
11. Banik BK, Samajdar S, Banik I, Zegrocka O and Becker FF: Indium-mediated stereospecific glycosylation of alcohols. Heterocycles 55: 227-230, 2001.
12. Banik BK, Lecea A, Arrieta A, Cozar A and Cossio FP: On the stereodivergent behavior observed in the Staudinger reaction between methoxyketene and (E)-N-benzylidenearyl amines. Angew Chem Int Ed 46: 3028-3032, 2007.
13. Banik BK, Manhas MS and Bose AK: Studies on lactams. Part 103. Enantiopure α-hydroxy-β-lactams via stereoselective glycosylation. Tetrahedron Lett 38: 5077-5080, 1997.
14. Hernandez AI , Balzarini J, Karlsson A, Camarasa MJ and Perez MJ: Acyclic nucleoside analogues as novel inhibitors of human mitochondrial. J Med Chem 45: 4254, 2002.