메뉴 건너뛰기




Volumn 46, Issue 1, 2003, Pages 12-15

Stereoselective synthesis of β-lactams with polyaromatic imines: Entry to new and novel anticancer agents

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; AZETIDINONE DERIVATIVE; BETA LACTAM DERIVATIVE; IMINE;

EID: 0037413527     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0255825     Document Type: Article
Times cited : (188)

References (43)
  • 2
    • 0034725762 scopus 로고    scopus 로고
    • Polyhydroxy amino acid derivatives via β-lactams using enantiospecific approaches and microwave techniques
    • (a) Manhas, M. S.; Banik, B. K.; Mathur, A.; Vincent, J. E.; Bose, A. K. Polyhydroxy Amino Acid Derivatives via β-Lactams Using Enantiospecific Approaches and Microwave Techniques. Tetrahedron, Symposium in Print 2000, 56, 5587-5601.
    • (2000) Tetrahedron, Symposium in Print , vol.56 , pp. 5587-5601
    • Manhas, M.S.1    Banik, B.K.2    Mathur, A.3    Vincent, J.E.4    Bose, A.K.5
  • 3
    • 0000120480 scopus 로고    scopus 로고
    • Microwave assisted synthesis of vinyl β-lactam: Synthons for natural products
    • (b) Bose, A. K.; Mathur, C.; Wagle, D. R.; Manhas, M. S. Microwave assisted synthesis of vinyl β-lactam: Synthons for natural products. Tetrahedron, Symposium in Print, 2000, 56, 5603-5619.
    • (2000) Tetrahedron, Symposium in Print , vol.56 , pp. 5603-5619
    • Bose, A.K.1    Mathur, C.2    Wagle, D.R.3    Manhas, M.S.4
  • 4
    • 0000096261 scopus 로고
    • Recent advances in the β-lactam synthon methodology
    • (c) Ojima, I. Recent advances in the β-lactam synthon methodology. Acc. Chem Res. 1995, 28, 383-389.
    • (1995) Acc. Chem Res. , vol.28 , pp. 383-389
    • Ojima, I.1
  • 5
    • 0001105785 scopus 로고
    • Stereospecific glycosylation via ferrier rearrangement for optical resolution
    • (d) Banik. B. K.; Manhas, M. S.; Bose, A. K. Stereospecific Glycosylation via Ferrier Rearrangement for Optical Resolution. J. Org. Chem. 1994, 59, 4714-4716.
    • (1994) J. Org. Chem. , vol.59 , pp. 4714-4716
    • Banik, B.K.1    Manhas, M.S.2    Bose, A.K.3
  • 6
    • 33751385575 scopus 로고
    • Versatile β-lactam synthons: Enantiospecific synthesis of (-)-ployoxamic acid
    • (e) Banik, B. K.; Manhas, M. S.; Bose, A. K. Versatile β-lactam synthons: Enantiospecific synthesis of (-)-ployoxamic acid. J. Org. Chem. 1993, 58, 307-309.
    • (1993) J. Org. Chem. , vol.58 , pp. 307-309
    • Banik, B.K.1    Manhas, M.S.2    Bose, A.K.3
  • 12
    • 0028282060 scopus 로고
    • Serine protease: (a) Mascaretti, O. A.; Boschetti, C. E.; Danelon, G. O. Mata; E. G.; Roveri, O. A. Curr. Med. Chem. 1995, 1, 441-470. (b) Edwards, P. D.; Bernstein, P. R. Med. Res. Rev. 1994, 14, 127-194.
    • (1994) Med. Res. Rev. , vol.14 , pp. 127-194
    • Edwards, P.D.1    Bernstein, P.R.2
  • 15
    • 0034405709 scopus 로고    scopus 로고
    • Synthesis of 3-unsubstituted ferrocenyl β-lactams by indium-induced reaction
    • (a) Ghatak, A.; Becker, F. F.; Banik, B. K. Synthesis of 3-unsubstituted ferrocenyl β-lactams by indium-induced reaction. Heterocycles 2000, 53, 2769-2772.
    • (2000) Heterocycles , vol.53 , pp. 2769-2772
    • Ghatak, A.1    Becker, F.F.2    Banik, B.K.3
  • 17
    • 0034686858 scopus 로고    scopus 로고
    • Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines
    • Banik, B. K.; Becker, F. F. Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines. Tetrahedron Lett. 2000, 41, 6551-6554.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 6551-6554
    • Banik, B.K.1    Becker, F.F.2
  • 18
    • 0035746425 scopus 로고    scopus 로고
    • Synthesis of tricyclic β-lactams via palladium acetate mediated Heck reaction
    • Ng, S.; Banik, I.; Okawa, A.; Becker, F. F.; Banik, B. K. Synthesis of tricyclic β-lactams via palladium acetate mediated 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
  • 19
    • 0012239005 scopus 로고    scopus 로고
    • Biological investigation of novel β-lactams as anticancer agents
    • Orlando, FL, April, MEDI-213
    • Banik, B. K.; Becker, F. F. Biological Investigation of Novel β-Lactams as Anticancer Agents. Presented at the American Chemical Society (ACS) National Meeting, Orlando, FL, April 2002, MEDI-213. We sent this paper for presentation to the ACS on October 31, 2001 and it was accepted on December 16, 2001. The drug synthesis and chemistry branch of the NCI tested 17a in their 60 cell lines and sent us the report on August 8, 2001.
    • (2002) American Chemical Society (ACS) National Meeting
    • Banik, B.K.1    Becker, F.F.2
  • 20
    • 0030814274 scopus 로고    scopus 로고
    • Immunologically specific activation of a cephalosporin derivative of mitomycin C by monoclonal antibody β-lactamase conjugates
    • Cephalosporin has been used as a prodrug to increase the antitumor activity of mitomycin C. Vrudhula, V.; Svensson, H. P.; Senter, P. D. Immunologically specific activation of a cephalosporin derivative of mitomycin C by monoclonal antibody β-lactamase conjugates. J. Med. Chem. 1997, 40, 2788-2792.
    • (1997) J. Med. Chem. , vol.40 , pp. 2788-2792
    • Vrudhula, V.1    Svensson, H.P.2    Senter, P.D.3
  • 21
    • 0032553002 scopus 로고    scopus 로고
    • Polycyclic aromatic compounds as anticancer agents: Synthesis and biological evaluation of some chrysene derivatives
    • (a) Becker, F. F.; Banik, B. K. Polycyclic Aromatic Compounds as Anticancer Agents: Synthesis and Biological Evaluation of Some Chrysene Derivatives. Bioorg., Med. Chem. Lett. 1998, 8, 2877-2880.
    • (1998) Bioorg., Med. Chem. Lett. , vol.8 , pp. 2877-2880
    • Becker, F.F.1    Banik, B.K.2
  • 22
    • 0033761583 scopus 로고    scopus 로고
    • Polycyclic aromatic compounds as anticancer agents: Synthesis and biological evaluation of dibenzofluorene derivatives
    • (b) Becker, F. F.; Mukhopadhyay, C.; Hackfeld, L.; Banik, I.; Banik, B. K. Polycyclic aromatic compounds as anticancer agents: Synthesis and biological evaluation of dibenzofluorene derivatives. Bioorg., Med. Chem. 2000, 8, 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
  • 23
    • 0035108369 scopus 로고    scopus 로고
    • Polycyclic aromatic compounds as anticancer agents: Structure-activity relationships of chrysene and pyrene derivatives
    • (c) Banik, B. K.; Becker, F. F. Polycyclic aromatic compounds as anticancer agents: Structure-activity relationships of chrysene and pyrene derivatives. Bioorg., Med. Chem. 2001, 9, 593-605.
    • (2001) Bioorg., Med. Chem. , vol.9 , pp. 593-605
    • Banik, B.K.1    Becker, F.F.2
  • 24
    • 0034827198 scopus 로고    scopus 로고
    • Synthesis, electrophilic substitution and structure-activity relationship studies of polycyclic aromatic compounds for the development of anticancer agents
    • (d) Banik, B. K.; Becker, F. F. Synthesis, electrophilic substitution and structure-activity relationship studies of polycyclic aromatic compounds for the development of anticancer agents. Curr. Med. Chem. 2001, 8, 1513-1533.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1513-1533
    • Banik, B.K.1    Becker, F.F.2
  • 25
    • 0012292521 scopus 로고    scopus 로고
    • US Patent 6015811, 2000
    • Also see: (a) Becker, F. F.; Banik, B. K. US Patent 6015811, 2000.
    • Becker, F.F.1    Banik, B.K.2
  • 27
    • 0012239613 scopus 로고    scopus 로고
    • US Patent 6362200, 2002
    • (c) Becker, F. F.; Banik, B. K. US Patent 6362200, 2002. The controls for the MTT assay were achieved by including in every run one of our previously reported, consistently active agents, as well as cisplatin. In the majority of the runs, one of our inactive agents was used as a negative control, but a run was not considered reliable unless at least one "new" agent in that run demonstrated positive and another negative activity. The consistency of the in vitro assay was examined by comparing given agents over a period of 20 months. Although there was occasional variation in the result of a given agent and cisplatin against a single tumor line, in the vast majority of the cases, the compound's status remained within its original activity classification.
    • Becker, F.F.1    Banik, B.K.2
  • 29
    • 0032190805 scopus 로고    scopus 로고
    • A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine
    • We have devised methods for the synthesis of polyaromatic nitro compounds and amines described in this paper. For example, see: (a) Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine. Tetrahedron Lett. 1998, 39, 7243-7247. (b) Banik, B. K.; Suhendra, M.; Banik, I.; Becker, F. F. Indium/ammonium chloride mediated reduction of aromatic nitro compounds: Practical synthesis of 6-amino chrysene. Synth. Commun. 2000, 30, 3745-3754. (c) Basu, M. K.; Becker, F. F.; Banik, B. K. Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride. Tetrahedron Lett. 2001, 41, 6551-6554. (d) Samajdar, S.; Becker, F. F.; Banik, B. K. Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate. Tetrahedron Lett. 2000, 41, 8017-8020.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7243-7247
    • Banik, B.K.1    Mukhopadhyay, C.2    Venkatraman, M.S.3    Becker, F.F.4
  • 30
    • 0033806181 scopus 로고    scopus 로고
    • Indium/ammonium chloride mediated reduction of aromatic nitro compounds: Practical synthesis of 6-amino chrysene
    • We have devised methods for the synthesis of polyaromatic nitro compounds and amines described in this paper. For example, see: (a) Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine. Tetrahedron Lett. 1998, 39, 7243-7247. (b) Banik, B. K.; Suhendra, M.; Banik, I.; Becker, F. F. Indium/ammonium chloride mediated reduction of aromatic nitro compounds: Practical synthesis of 6-amino chrysene. Synth. Commun. 2000, 30, 3745-3754. (c) Basu, M. K.; Becker, F. F.; Banik, B. K. Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride. Tetrahedron Lett. 2001, 41, 6551-6554. (d) Samajdar, S.; Becker, F. F.; Banik, B. K. Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate. Tetrahedron Lett. 2000, 41, 8017-8020.
    • (2000) Synth. Commun. , vol.30 , pp. 3745-3754
    • Banik, B.K.1    Suhendra, M.2    Banik, I.3    Becker, F.F.4
  • 31
    • 0034702560 scopus 로고    scopus 로고
    • Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride
    • We have devised methods for the synthesis of polyaromatic nitro compounds and amines described in this paper. For example, see: (a) Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine. Tetrahedron Lett. 1998, 39, 7243-7247. (b) Banik, B. K.; Suhendra, M.; Banik, I.; Becker, F. F. Indium/ammonium chloride mediated reduction of aromatic nitro compounds: Practical synthesis of 6-amino chrysene. Synth. Commun. 2000, 30, 3745-3754. (c) Basu, M. K.; Becker, F. F.; Banik, B. K. Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride. Tetrahedron Lett. 2001, 41, 6551-6554. (d) Samajdar, S.; Becker, F. F.; Banik, B. K. Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate. Tetrahedron Lett. 2000, 41, 8017-8020.
    • (2001) Tetrahedron Lett. , vol.41 , pp. 6551-6554
    • Basu, M.K.1    Becker, F.F.2    Banik, B.K.3
  • 32
    • 0034649133 scopus 로고    scopus 로고
    • Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate
    • We have devised methods for the synthesis of polyaromatic nitro compounds and amines described in this paper. For example, see: (a) Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine. Tetrahedron Lett. 1998, 39, 7243-7247. (b) Banik, B. K.; Suhendra, M.; Banik, I.; Becker, F. F. Indium/ammonium chloride mediated reduction of aromatic nitro compounds: Practical synthesis of 6-amino chrysene. Synth. Commun. 2000, 30, 3745-3754. (c) Basu, M. K.; Becker, F. F.; Banik, B. K. Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride. Tetrahedron Lett. 2001, 41, 6551-6554. (d) Samajdar, S.; Becker, F. F.; Banik, B. K. Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate. Tetrahedron Lett. 2000, 41, 8017-8020.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 8017-8020
    • Samajdar, S.1    Becker, F.F.2    Banik, B.K.3
  • 33
    • 0033525683 scopus 로고    scopus 로고
    • A convenient trans-stereoselective synthesis of phenanthridine derived 2-azetidinones using the Staudinger Ketene-Imine cycloaddition
    • (a) Alcaide, B.; Vicente-Rodriguez, A. A Convenient trans-stereoselective synthesis of phenanthridine derived 2-azetidinones using the Staudinger Ketene-Imine cycloaddition. Tetrahedron Lett. 1999, 40, 2005-2006.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2005-2006
    • Alcaide, B.1    Vicente-Rodriguez, A.2
  • 35
    • 0027761171 scopus 로고
    • Synthesis of trans-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one. A key starting β-lactam for 2-epi-taxol
    • (c) Endo, M.; 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. 1993, 3, 2483-2486.
    • (1993) Bioorg., Med. Chem. Lett. , vol.3 , pp. 2483-2486
    • Endo, M.1    Droghini, R.2
  • 36
    • 0028891310 scopus 로고
    • Stereocontrol of β-lactam formation using microwave irradiation
    • (d) Bose, A. K.; Banik, B. K.; Manhas, M. S. Stereocontrol of β-lactam formation using microwave irradiation. Tetrahedron Lett. 1995, 36, 213-216.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 213-216
    • Bose, A.K.1    Banik, B.K.2    Manhas, M.S.3
  • 37
    • 0000344501 scopus 로고    scopus 로고
    • Origins of the stereodivergent outcome in the Staudinger reaction between acyl chlorides and imines
    • (a) Arrieta, A.; Lecea, B.; Cossio, F. P. Origins of the stereodivergent outcome in the Staudinger reaction between acyl chlorides and imines. J. Org. Chem. 1998, 63, 5869-5876.
    • (1998) J. Org. Chem. , vol.63 , pp. 5869-5876
    • Arrieta, A.1    Lecea, B.2    Cossio, F.P.3
  • 38
    • 0028109179 scopus 로고
    • Chiral control in the Staudinger reaction between ketenes and imines: A theoretical SCF-MO study on asymmetric torquoselectivity
    • Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. Chiral control in the Staudinger reaction between ketenes and imines: A theoretical SCF-MO study on asymmetric torquoselectivity. J. Am. Chem. Soc. 1994, 116, 2085-2093.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2085-2093
    • Cossio, F.P.1    Arrieta, A.2    Lecea, B.3    Ugalde, J.M.4
  • 39
    • 0027516557 scopus 로고
    • A semiempirical theoretical study on the formation of β-lactams from ketenes and imines
    • Cossio, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C. A semiempirical theoretical study on the formation of β-lactams from ketenes and imines. J. Am. Chem. Soc. 1993, 115, 995-1004.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 995-1004
    • Cossio, F.P.1    Ugalde, J.M.2    Lopez, X.3    Lecea, B.4    Palomo, C.5
  • 40
    • 0024323722 scopus 로고
    • Mechanism of an acid chloride-imine reaction by low-temperature FT-IR: β-lactam formation occurs exclusively through a ketene intermediate
    • Lynch, J. E.; Riseman, S. M.; Laswell, W. L.; Tschaen, D. M.; Volante, R. P.; Smith, G.; Shinkai, I. Mechanism of an acid chloride-imine reaction by low-temperature FT-IR: β-lactam formation occurs exclusively through a ketene intermediate. J. Org. Chem. 1989, 54, 3792-3796.
    • (1989) J. Org. Chem. , vol.54 , pp. 3792-3796
    • Lynch, J.E.1    Riseman, S.M.2    Laswell, W.L.3    Tschaen, D.M.4    Volante, R.P.5    Smith, G.6    Shinkai, I.7
  • 41
    • 0001695634 scopus 로고
    • β-lactams. Cis-fused β-lactams from substituted cinnamaldene anilines and azidoacetyl chloride: Scope and limitations
    • Just, G.; Ugolini, A.; Zamboni, R. β-lactams. Cis-fused β-lactams from substituted cinnamaldene anilines and azidoacetyl chloride: Scope and limitations. Synth. Commun. 1979, 9, 117-121.
    • (1979) Synth. Commun. , vol.9 , pp. 117-121
    • Just, G.1    Ugolini, A.2    Zamboni, R.3
  • 43
    • 0002813624 scopus 로고
    • Studies on the mechanism of β-lactam formation
    • Bose, A. K.; Chiang, Y. H.; Manhas, M. S. Studies on the mechanism of β-lactam formation. Tetrahedron Lett. 1972, 4091-4094.
    • (1972) Tetrahedron Lett. , pp. 4091-4094
    • Bose, A.K.1    Chiang, Y.H.2    Manhas, M.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.