메뉴 건너뛰기




Volumn 39, Issue 26, 1996, Pages 5072-5082

Design, synthesis, and evaluation of nonpeptidic inhibitors of human rhinovirus 3C protease

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 BENZO[B]THIOPHENYLMETHYL)ISATIN 5 CARBOXAMIDE; 1 METHYLISATIN 5 CARBOXAMIDE; CINNAMYLISATIN 5 CARBOXAMIDE; ISATIN DERIVATIVE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; VIRUS ENZYME;

EID: 12644306888     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960603e     Document Type: Article
Times cited : (150)

References (54)
  • 1
    • 0000824034 scopus 로고
    • Rhinoviruses
    • Fields, B. N., Knipe, D. M., Eds.; Raven Press: New York, Chapter 22
    • (a) Couch, R. B. Rhinoviruses. In Virology; Fields, B. N., Knipe, D. M., Eds.; Raven Press: New York, 1990; Vol. 1, Chapter 22, pp 607-629.
    • (1990) Virology , vol.1 , pp. 607-629
    • Couch, R.B.1
  • 2
    • 0026803235 scopus 로고
    • Treatment of the Picornavirus Common Cold by Inhibitors of Viral Uncoating and Attachment
    • and references cited therein
    • (b) See: McKinlay, M. A.; Pevear, D. C.; Rossman, M. G. Treatment of the Picornavirus Common Cold by Inhibitors of Viral Uncoating and Attachment. Annu. Rev. Microbiol. 1992, 46, 635-654 and references cited therein. (c) Phillpotts, R. J.; Tyrell, D. A. J. Rhinovirus Colds. Br. Med. Bull. 1985, 41, 386-390. (d) Gwaltney, J. M. Rhinoviruses. In Viral Infections of Humans; Evans, A. S., Ed.; Plenum Publishing Corp.: New York, 1982; Chapter 20, pp 491-517. (e) Gwaltney, J. M. The Common Cold. In Principles and Practices of Infectious Diseases; Mandell, G. L., Douglas, R. G., Bennett, J. E., Eds.; John Wiley & Sons: New York, 1985; Chapter 38, pp 351-355.
    • (1992) Annu. Rev. Microbiol. , vol.46 , pp. 635-654
    • McKinlay, M.A.1    Pevear, D.C.2    Rossman, M.G.3
  • 3
    • 0022410295 scopus 로고
    • Rhinovirus Colds
    • (b) See: McKinlay, M. A.; Pevear, D. C.; Rossman, M. G. Treatment of the Picornavirus Common Cold by Inhibitors of Viral Uncoating and Attachment. Annu. Rev. Microbiol. 1992, 46, 635-654 and references cited therein. (c) Phillpotts, R. J.; Tyrell, D. A. J. Rhinovirus Colds. Br. Med. Bull. 1985, 41, 386-390. (d) Gwaltney, J. M. Rhinoviruses. In Viral Infections of Humans; Evans, A. S., Ed.; Plenum Publishing Corp.: New York, 1982; Chapter 20, pp 491-517. (e) Gwaltney, J. M. The Common Cold. In Principles and Practices of Infectious Diseases; Mandell, G. L., Douglas, R. G., Bennett, J. E., Eds.; John Wiley & Sons: New York, 1985; Chapter 38, pp 351-355.
    • (1985) Br. Med. Bull. , vol.41 , pp. 386-390
    • Phillpotts, R.J.1    Tyrell, D.A.J.2
  • 4
    • 0026803235 scopus 로고
    • Rhinoviruses
    • Evans, A. S., Ed.; Plenum Publishing Corp.: New York, Chapter 20
    • (b) See: McKinlay, M. A.; Pevear, D. C.; Rossman, M. G. Treatment of the Picornavirus Common Cold by Inhibitors of Viral Uncoating and Attachment. Annu. Rev. Microbiol. 1992, 46, 635-654 and references cited therein. (c) Phillpotts, R. J.; Tyrell, D. A. J. Rhinovirus Colds. Br. Med. Bull. 1985, 41, 386-390. (d) Gwaltney, J. M. Rhinoviruses. In Viral Infections of Humans; Evans, A. S., Ed.; Plenum Publishing Corp.: New York, 1982; Chapter 20, pp 491-517. (e) Gwaltney, J. M. The Common Cold. In Principles and Practices of Infectious Diseases; Mandell, G. L., Douglas, R. G., Bennett, J. E., Eds.; John Wiley & Sons: New York, 1985; Chapter 38, pp 351-355.
    • (1982) Viral Infections of Humans , pp. 491-517
    • Gwaltney, J.M.1
  • 5
    • 0026803235 scopus 로고
    • The Common Cold
    • Mandell, G. L., Douglas, R. G., Bennett, J. E., Eds.; John Wiley & Sons: New York, Chapter 38
    • (b) See: McKinlay, M. A.; Pevear, D. C.; Rossman, M. G. Treatment of the Picornavirus Common Cold by Inhibitors of Viral Uncoating and Attachment. Annu. Rev. Microbiol. 1992, 46, 635-654 and references cited therein. (c) Phillpotts, R. J.; Tyrell, D. A. J. Rhinovirus Colds. Br. Med. Bull. 1985, 41, 386-390. (d) Gwaltney, J. M. Rhinoviruses. In Viral Infections of Humans; Evans, A. S., Ed.; Plenum Publishing Corp.: New York, 1982; Chapter 20, pp 491-517. (e) Gwaltney, J. M. The Common Cold. In Principles and Practices of Infectious Diseases; Mandell, G. L., Douglas, R. G., Bennett, J. E., Eds.; John Wiley & Sons: New York, 1985; Chapter 38, pp 351-355.
    • (1985) Principles and Practices of Infectious Diseases , pp. 351-355
    • Gwaltney, J.M.1
  • 6
    • 0023947898 scopus 로고
    • Viral Proteinases
    • and references cited therein
    • See: Kräusslich, H.-G.; Wimmer, E. Viral Proteinases. Annu. Rev. Biochem. 1988, 57, 701-754 and references cited therein.
    • (1988) Annu. Rev. Biochem. , vol.57 , pp. 701-754
    • Kräusslich, H.-G.1    Wimmer, E.2
  • 8
    • 0000700098 scopus 로고
    • Molecular cloning and complete sequence determination of the RNA genome of human rhinovirus type 14
    • (a) Callahan, P. L.; Mizutani, S.; Colonno, R. J. Molecular cloning and complete sequence determination of the RNA genome of human rhinovirus type 14. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 732-736.
    • (1985) Proc. Natl. Acad. Sci. U.S.A. , vol.82 , pp. 732-736
    • Callahan, P.L.1    Mizutani, S.2    Colonno, R.J.3
  • 9
    • 0021770960 scopus 로고
    • The complete nucleotide sequence of the common cold virus: Human rhinovirus 14
    • (b) Stanway, G.; Hughes, P. J.; Mountford, R. C.; Minor, P. D.; Almond, J. W. The complete nucleotide sequence of the common cold virus: human rhinovirus 14. Nucleic Acids Res. 1984, 12, 7859-7875.
    • (1984) Nucleic Acids Res. , vol.12 , pp. 7859-7875
    • Stanway, G.1    Hughes, P.J.2    Mountford, R.C.3    Minor, P.D.4    Almond, J.W.5
  • 10
    • 0028607508 scopus 로고
    • Complete sequence of the RNA genome of human rhinovirus 16, a clinically useful common cold virus belonging to the ICAM-1 receptor group
    • (c) Lee, W.-M.; Wang, W.; Rueckart, R. R. Complete sequence of the RNA genome of human rhinovirus 16, a clinically useful common cold virus belonging to the ICAM-1 receptor group. Virus Genes 1995, 9, 177-181.
    • (1995) Virus Genes , vol.9 , pp. 177-181
    • Lee, W.-M.1    Wang, W.2    Rueckart, R.R.3
  • 11
    • 0024468899 scopus 로고
    • Hydrolysis of a Series of Synthetic Peptide Substrates by the Human Rhinovirus 14 3C Protease, Cloned and Express in Escherichia coli
    • (a) Orr, D. C.; Long, A. C.; Kay, J.; Dunn, B. M.; Cameron, J. M. Hydrolysis of a Series of Synthetic Peptide Substrates by the Human Rhinovirus 14 3C Protease, Cloned and Express in Escherichia coli. J. Gen. Virol. 1989, 70, 2931-2942.
    • (1989) J. Gen. Virol. , vol.70 , pp. 2931-2942
    • Orr, D.C.1    Long, A.C.2    Kay, J.3    Dunn, B.M.4    Cameron, J.M.5
  • 12
    • 0024431580 scopus 로고
    • Cleavage of Small Peptides in Vitro by Human Rhinovirus 14 3C Protease Expressed in Escherichia coli
    • (b) Cordingly, M. G.; Register, R. B.; Callahan, P. L.; Garsky, V. M.; Colonno, R. J. Cleavage of Small Peptides In Vitro by Human Rhinovirus 14 3C Protease Expressed in Escherichia coli. J. Virol. 1989, 63, 5037-5045.
    • (1989) J. Virol. , vol.63 , pp. 5037-5045
    • Cordingly, M.G.1    Register, R.B.2    Callahan, P.L.3    Garsky, V.M.4    Colonno, R.J.5
  • 14
    • 0000686943 scopus 로고
    • Viral cysteine proteases are homologous to the trypsin-like family of serine proteases: Structural and functional implications
    • (b) Bazan, J. F.; Fletterick, R. J. Viral cysteine proteases are homologous to the trypsin-like family of serine proteases: Structural and functional implications. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 7872-7876.
    • (1988) Proc. Natl. Acad. Sci. U.S.A. , vol.85 , pp. 7872-7876
    • Bazan, J.F.1    Fletterick, R.J.2
  • 15
    • 0022570578 scopus 로고
    • Poliovirus-encoded Proteinase 3C: A Possible Evolutionary Link between Cellular Serine and Cysteine Proteinase Families
    • (c) Gorbalenya, A. E.; Blinov, V. M.; Donchenko, A. P. Poliovirus-encoded Proteinase 3C: A Possible Evolutionary Link Between Cellular Serine and Cysteine Proteinase Families. FEBS Lett. 1986, 194, 253-257.
    • (1986) FEBS Lett. , vol.194 , pp. 253-257
    • Gorbalenya, A.E.1    Blinov, V.M.2    Donchenko, A.P.3
  • 16
    • 0028328469 scopus 로고
    • Picornaviral 3C cysteine proteinases have a fold similar to chymotrypsin-like serine proteinases
    • (d) Allaire, M.; Chernala, M. M.; Malcolm, B. A.; James, M. N. G. Picornaviral 3C cysteine proteinases have a fold similar to chymotrypsin-like serine proteinases. Nature 1994, 369, 72-76.
    • (1994) Nature , vol.369 , pp. 72-76
    • Allaire, M.1    Chernala, M.M.2    Malcolm, B.A.3    James, M.N.G.4
  • 17
    • 0030012893 scopus 로고    scopus 로고
    • Synthesis and Activity of Piperizine-containing Antirhinoviral Agents and Crystal Structure of SDZ 880-061 Bound to Human Rhinovirus 14
    • and references cited therein
    • See Oren, D. A.; Zhang, A.; Nesvadba, H.; Rosenwirth, B.; Arnold, E. Synthesis and Activity of Piperizine-containing Antirhinoviral Agents and Crystal Structure of SDZ 880-061 Bound to Human Rhinovirus 14. J. Mol. Biol. 1996, 259, 120-134 and references cited therein.
    • (1996) J. Mol. Biol. , vol.259 , pp. 120-134
    • Oren, D.A.1    Zhang, A.2    Nesvadba, H.3    Rosenwirth, B.4    Arnold, E.5
  • 18
    • 0025677291 scopus 로고
    • Spiro Indolinone Beta-lactams, Inhibitors of Poliovirus and Rhinovirus 3C-Proteinases
    • (a) Skiles, J. W.; McNeil, D. Spiro Indolinone Beta-lactams, Inhibitors of Poliovirus and Rhinovirus 3C-Proteinases. Tetrahedron Lett. 1990, 31, 7277-7280.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7277-7280
    • Skiles, J.W.1    McNeil, D.2
  • 20
    • 0025868141 scopus 로고
    • Structure and Stereochemistry of Thysanone: A Novel Human Rhinovirus 3C-Protease Inhibitor from Thysanophora penicilloides
    • (c) Singh, S. B.; Cordingley, M. G.; Ball, R. G.; Smith, J. L.; Dombrowski, A. W.; Goetz, M. A. Structure and Stereochemistry of Thysanone: A Novel Human Rhinovirus 3C-Protease Inhibitor from Thysanophora penicilloides. Tetrahedron Lett. 1991, 32, 5279-5282.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 5279-5282
    • Singh, S.B.1    Cordingley, M.G.2    Ball, R.G.3    Smith, J.L.4    Dombrowski, A.W.5    Goetz, M.A.6
  • 25
    • 84986512474 scopus 로고
    • CHARMM: A Program for Macromolecular Energy, Minimization, and Dynamics Calculations
    • Models of peptides bound to HRV-14 3CP were created from a combination of constrained molecular dynamics and molecular mechanics minimizations using the CHARMM software: Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Kaplus, M. CHARMM: A Program for Macromolecular Energy, Minimization, and Dynamics Calculations. J. Comput. Chem. 1983, 4, 187-217.
    • (1983) J. Comput. Chem. , vol.4 , pp. 187-217
    • Brooks, B.R.1    Bruccoleri, R.E.2    Olafson, B.D.3    States, D.J.4    Swaminathan, S.5    Kaplus, M.6
  • 26
    • 0028848890 scopus 로고    scopus 로고
    • Lilly Research Laboratories, Indianapolis, IN 46285, personal communication
    • During the course of our research, isatin derivatives have been reported to be inhibitors of serine and cysteine proteases. (a) This class of compounds was discovered by a screening program; Spitzer, W. A. Lilly Research Laboratories, Indianapolis, IN 46285, personal communication. (b) Iyers, R. A.; Hanna, P. E. N-(Carbobenzyloxy)isatin: A Slow Binding α-Keto Lactam Inhibitor of α-Chymotrypsin. Bioorg. Med. Chem. Lett. 1995, 5, 89-92.
    • Spitzer, W.A.1
  • 27
    • 0028848890 scopus 로고    scopus 로고
    • N-(Carbobenzyloxy)isatin: A Slow Binding α-Keto Lactam Inhibitor of α-Chymotrypsin
    • During the course of our research, isatin derivatives have been reported to be inhibitors of serine and cysteine proteases. (a) This class of compounds was discovered by a screening program; Spitzer, W. A. Lilly Research Laboratories, Indianapolis, IN 46285, personal communication. (b) Iyers, R. A.; Hanna, P. E. N-(Carbobenzyloxy)isatin: A Slow Binding α-Keto Lactam Inhibitor of α-Chymotrypsin. Bioorg. Med. Chem. Lett. 1995, 5, 89-92.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 89-92
    • Iyers, R.A.1    Hanna, P.E.2
  • 31
    • 84986437005 scopus 로고
    • MacroModel - An Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics
    • Modeling exercises were performed with MacroModel: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. MacroModel - An Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-467.
    • (1990) J. Comput. Chem. , vol.11 , pp. 440-467
    • Mohamadi, F.1    Richards, N.G.J.2    Guida, W.C.3    Liskamp, R.4    Lipton, M.5    Caufield, C.6    Chang, G.7    Hendrickson, T.8    Still, W.C.9
  • 32
    • 12644302576 scopus 로고    scopus 로고
    • note
    • See the Experimental Section for methods and details of the ab initio quantum mechanical calculations.
  • 33
    • 6944251055 scopus 로고
    • Note on the Approximation Treatment for Many-Electron Systems
    • (a) Møller, C.; Plesset, M. S. Note on the Approximation Treatment for Many-Electron Systems. Phys. Rev. 1934, 46, 618-622.
    • (1934) Phys. Rev. , vol.46 , pp. 618-622
    • Møller, C.1    Plesset, M.S.2
  • 34
    • 84987058929 scopus 로고
    • Variational Configuration Interaction Methods and Comparison with Perturbation Theory
    • (b) Pople, J. A.; Seeger, R.; Krishnan, R. Variational Configuration Interaction Methods and Comparison with Perturbation Theory. Int. J. Quant. Chem. Symp. 1977, 11, 149-163.
    • (1977) Int. J. Quant. Chem. Symp. , vol.11 , pp. 149-163
    • Pople, J.A.1    Seeger, R.2    Krishnan, R.3
  • 35
    • 0000649832 scopus 로고
    • Contribution of triple substitutions to the electron correlation energy in fourth order perturbation theory
    • (c) Krishnan, R.; Frisch, M. J.; Pople, J. A. Contribution of triple substitutions to the electron correlation energy in fourth order perturbation theory. J. Chem. Phys. 1980, 72, 4244-4245.
    • (1980) J. Chem. Phys. , vol.72 , pp. 4244-4245
    • Krishnan, R.1    Frisch, M.J.2    Pople, J.A.3
  • 36
    • 12644256029 scopus 로고    scopus 로고
    • note
    • 1 were collected at 4 °C on a Rigaku AFC-5 diffractometer equipped with a graphite monochromator and a dual chamber area detector system of the Xuong-Hamlin design. Cell parameters are a = 34.43, b = 66.48, c = 77.86; α = β = γ = 90°. These data are 94% complete to 2.8 Å resolution (average redundancy is 4.5) with a scaling R factor on intensities of 0.113.
  • 37
    • 0027264002 scopus 로고
    • Diaminomethane dihydrochloride, a novel reagent for the synthesis of primary amides of amino acids and peptides from active esters
    • Galaverna, G.; Corradini, R.; Dossena, A.; Marchelli, R. Diaminomethane dihydrochloride, a novel reagent for the synthesis of primary amides of amino acids and peptides from active esters. Int. J. Pept. Protein Res. 1993, 42, 53-57.
    • (1993) Int. J. Pept. Protein Res. , vol.42 , pp. 53-57
    • Galaverna, G.1    Corradini, R.2    Dossena, A.3    Marchelli, R.4
  • 38
    • 0038643944 scopus 로고
    • Reactions of Isatin Dimethyl Ketal and its Ethyl Imino Ether with Methyllithium
    • Wenkert, E.; Hudlicky, T. Reactions of Isatin Dimethyl Ketal and its Ethyl Imino Ether with Methyllithium. Synth. Commun. 1977, 7, 541-547.
    • (1977) Synth. Commun. , vol.7 , pp. 541-547
    • Wenkert, E.1    Hudlicky, T.2
  • 39
    • 12644269575 scopus 로고
    • Katritky, A. R., Meth-Cohn, O., Rees C. W., Eds.; Academic Press: London, Chapter 6
    • Heck, R. F. In Palladium Reagents in Organic Syntheses; Katritky, A. R., Meth-Cohn, O., Rees C. W., Eds.; Academic Press: London, 1985; Chapter 6, pp 308-311.
    • (1985) Palladium Reagents in Organic Syntheses , pp. 308-311
    • Heck, R.F.1
  • 40
    • 0346184325 scopus 로고
    • Synthesis of Functionalized Styrenes via Palladium-Catalyzed Coupling of Aryl Bromides with Vinyl Tin Reagents
    • McKean, D. R.; Parrinello, G.; Renaldo, A. F.; Stille, J. K. Synthesis of Functionalized Styrenes via Palladium-Catalyzed Coupling of Aryl Bromides with Vinyl Tin Reagents. J. Org. Chem. 1987, 52, 422-424.
    • (1987) J. Org. Chem. , vol.52 , pp. 422-424
    • McKean, D.R.1    Parrinello, G.2    Renaldo, A.F.3    Stille, J.K.4
  • 41
    • 85028795000 scopus 로고
    • Über Methylmerkaptoatophane
    • Brand, K.; Völcker, E. Über Methylmerkaptoatophane. Arch. Pharm. 1934, 272, 257-268.
    • (1934) Arch. Pharm. , vol.272 , pp. 257-268
    • Brand, K.1    Völcker, E.2
  • 43
    • 0025053937 scopus 로고
    • Design and Synthesis of New Fluorogenic HIV Protease Substrates Based on Resonance Energy Transfer
    • (b) Wang, G. T.; Matayoshi, E.; Huffaker, H. J.; Krafft, G. A. Design and Synthesis of New Fluorogenic HIV Protease Substrates Based on Resonance Energy Transfer. Tetrahedron Lett. 1990, 31, 6493-6496.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6493-6496
    • Wang, G.T.1    Matayoshi, E.2    Huffaker, H.J.3    Krafft, G.A.4
  • 44
    • 12644276778 scopus 로고    scopus 로고
    • note
    • Assays were performed using commercially available proteases essentially as described by the supplier.
  • 45
    • 0024578841 scopus 로고
    • New Soluble-Formazan Assay for HIV-1 Cytopathic Effects: Application to High-Flux Screening of Synthetic and Natural Products for Aids-Antiviral Activity
    • Weislow, O. S.; Kiser, R.; Fine, D. L.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. New Soluble-Formazan Assay for HIV-1 Cytopathic Effects: Application to High-Flux Screening of Synthetic and Natural Products for Aids-Antiviral Activity. J. Natl. Cancer Inst. 1989, 81, 577-586.
    • (1989) J. Natl. Cancer Inst. , vol.81 , pp. 577-586
    • Weislow, O.S.1    Kiser, R.2    Fine, D.L.3    Bader, J.4    Shoemaker, R.H.5    Boyd, M.R.6
  • 46
    • 0002522429 scopus 로고    scopus 로고
    • Mechanisms of Toxicology
    • Klaassen, C. D., Amdur, M. O., Doull, J., Eds.; McGraw-Hill: New York, Chapter 3
    • See: Zoltán, G.; Klaassen, C. D. Mechanisms of Toxicology. In Toxicology; The Basic Science of Poisons; Klaassen, C. D., Amdur, M. O., Doull, J., Eds.; McGraw-Hill: New York, 1996; Chapter 3, pp 35-74.
    • (1996) Toxicology; the Basic Science of Poisons , pp. 35-74
    • Zoltán, G.1    Klaassen, C.D.2
  • 47
    • 0027532370 scopus 로고
    • Role of Maturation Cleavage in Infectivity of Picornaviruses: Activation of an Infectosome
    • Lee, W.-M.; Monroe, S. S.; Rueckart, R. R. Role of Maturation Cleavage in Infectivity of Picornaviruses: Activation of an Infectosome. J. Virol. 1993, 67, 2110-2122.
    • (1993) J. Virol. , vol.67 , pp. 2110-2122
    • Lee, W.-M.1    Monroe, S.S.2    Rueckart, R.R.3
  • 49
    • 12644292295 scopus 로고    scopus 로고
    • note
    • The details pertaining to this protonated thiol model will be presented elsewhere.
  • 50
    • 0006018533 scopus 로고
    • Untersuchungen über Isatin und verwandte Verbindungen, VI; Über 5-Jod-isatin und 5.5′-Dijod-indigo
    • Borsche, W.; Weussmann, H.; Fritzsche, A. Untersuchungen über Isatin und verwandte Verbindungen, VI; Über 5-Jod-isatin und 5.5′-Dijod-indigo. Chem. Ber. 1924, 57, 1770-1775.
    • (1924) Chem. Ber. , vol.57 , pp. 1770-1775
    • Borsche, W.1    Weussmann, H.2    Fritzsche, A.3
  • 51
    • 2242419359 scopus 로고
    • Ricerche sugli eterociclici: Spettri di assorbimento u.v. e proprieta cromoforiche. - Nota II. Isatine
    • Mangini, A.; Passerini, R. Ricerche sugli eterociclici: spettri di assorbimento u.v. e proprieta cromoforiche. - Nota II. Isatine. Gazz. Chim. Ital. 1955, 85, 840-880.
    • (1955) Gazz. Chim. Ital. , vol.85 , pp. 840-880
    • Mangini, A.1    Passerini, R.2
  • 52
    • 0003626919 scopus 로고
    • Untersuchungen über Isatin und verwandte Verbindungen, V: Über Nitro-isatine
    • Borsche, W.; Weussmann, H.; Fritzsche, A. Untersuchungen über Isatin und verwandte Verbindungen, V: Über Nitro-isatine. Chem. Ber. 1924, 57, 1149-1152.
    • (1924) Chem. Ber. , vol.57 , pp. 1149-1152
    • Borsche, W.1    Weussmann, H.2    Fritzsche, A.3
  • 53
    • 0039156902 scopus 로고
    • Sommelet-Hauser Rearrangement of Oxygen and Sulfur Containing Heteroaromatic Sulfonium Ylides
    • and references cited therein
    • Yamamoto, M.; Kikinuma, M.; Kohmoto, S.; Yamada, K. Sommelet-Hauser Rearrangement of Oxygen and Sulfur Containing Heteroaromatic Sulfonium Ylides. Bull. Chem. Soc. Jpn. 1989, 62, 958-960 and references cited therein.
    • (1989) Bull. Chem. Soc. Jpn. , vol.62 , pp. 958-960
    • Yamamoto, M.1    Kikinuma, M.2    Kohmoto, S.3    Yamada, K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.