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Volumn 37, Issue 24, 1996, Pages 4113-4116

New cytochalasins: Synthetic studies of a novel HIV-1 protease inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHALASIN; PROTEINASE INHIBITOR; TITANIUM; VIRUS ENZYME;

EID: 0029952352     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00778-2     Document Type: Article
Times cited : (14)

References (42)
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    • (1992) Annual Reports in Medicinal Chemistry , pp. 271-289
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    • For some exceptions see Erickson, J. W.; Fesik, S. W. In Annual Reports in Medicinal Chemistry; Venuti, M. C., Ed.; Academic Press, San Diego, 1992; pp. 271-289, Potts, C. M.; Faulkner, D. J.; Chan, J. A.; Simolike, G. C.; Offen, P.; Hemling, M. E.; Francis, T. A. J. Am. Chem. Soc. 1991, 113, 6321-6322. Kuntz, I. D. Science 1992, 257, 1078-1082.
    • (1992) Science , vol.257 , pp. 1078-1082
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  • 18
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    • Cytochalasins, biochemical and cell biological aspects
    • Tanenbaum, S. W., Ed.; North Holland Publishing Co.: Amsterdam
    • (a) Tamm, C. Cytochalasins, Biochemical and Cell Biological Aspects; In Frontiers of Biology, Tanenbaum, S. W., Ed.; North Holland Publishing Co.: Amsterdam 1978; Vol. 46, pp. 15
    • (1978) Frontiers of Biology , vol.46 , pp. 15
    • Tamm, C.1
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    • (1981) J. Org. Chem. , vol.46 , pp. 5383-5389
    • Weinreb, S.M.1    Kim, M.Y.2    Starret, J.E.3
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    • (b) Weinreb, S. M.; Kim, M.Y.; Starret, J. E. J. Org. Chem. 1981, 46, 5383-5389. In a somewhat related approach to functionalizing C-10 Tamm and co-workers have described an approach from glutamic acid. Tamm, C.; Ackermann, J.; Matthes, M. Helv. Chim. Acta. 1990, 73, 122-132.
    • (1990) Helv. Chim. Acta. , vol.73 , pp. 122-132
    • Tamm, C.1    Ackermann, J.2    Matthes, M.3
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    • and references therein
    • (a) For a recent review see Thomas, E. J. Acc. Chem. Res. 1991, 24, 229-235 and references therein.
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    • Thomas, E.J.1
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    • (b) Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Smith, R. A. J. J. Org. Chem. 1989, 54, 4977-4979. See also Mehta, B. K.; Ila, H.; Junjappa, H. Tetraherdon Lett. 1995, 36(11), 1925-1928. The stereochemistry was anticipated based on the conformation of the intermediate iminium ion, but was rigorously established using a combination of NMR techniques. Cosy and hmqc spectra were recorded at 500MHz.
    • (1989) J. Org. Chem. , vol.54 , pp. 4977-4979
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  • 38
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    • The stereochemistry was anticipated based on the conformation of the intermediate iminium ion, but was rigorously established using a combination of NMR techniques. Cosy and hmqc spectra were recorded at 500MHz
    • (b) Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Smith, R. A. J. J. Org. Chem. 1989, 54, 4977-4979. See also Mehta, B. K.; Ila, H.; Junjappa, H. Tetraherdon Lett. 1995, 36(11), 1925-1928. The stereochemistry was anticipated based on the conformation of the intermediate iminium ion, but was rigorously established using a combination of NMR techniques. Cosy and hmqc spectra were recorded at 500MHz.
    • (1995) Tetraherdon Lett. , vol.36 , Issue.11 , pp. 1925-1928
    • Mehta, B.K.1    Ila, H.2    Junjappa, H.3
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    • Evans, D. A.; Urpi, F.; Somers, T. C.; Clark, J. S.; Bilodeau J. J. Am. Chem. Soc. 1990, 112, 8215-8216. Evans, D. A.; Rieger, D. L.; Bilodeau, J.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047-1050.
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    • Evans, D.A.1    Rieger, D.L.2    Bilodeau, J.3    Urpi, F.4
  • 41
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    • note
    • Further manipulations to produce functionalities present in the natural product but lacking the macrocyclic ring were achieved using procedures described in the literature. For example see reference 10b.
  • 42
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    • Advanced ACS Abstracts August 1993
    • None of the intermediates shown or analogs which lack the macrocyclic ring were active in the enzyme inhibition assay. Portions of that work has been published in: Advanced ACS Abstracts August 1993.


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