Synthesis and antitumor activity of leinamycin derivatives: Modifications of C-8 hydroxy and C-9 keto groups

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 8, 1998, Pages 909-912

  Kanda, Yutaka ^a   Ashizawa, Tadashi ^a   Saitoh, Yutaka ^a   Saito, Hiromitsu ^a   Gomi, Katsushige ^a   Okabe, Masami ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LEINAMYCIN;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; DIASTEREOISOMER; DNA CLEAVAGE; DRUG CONJUGATION; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

ANTIBIOTICS, ANTINEOPLASTIC; CELL DIVISION; HELA CELLS; HUMANS; INDICATORS AND REAGENTS; LACTAMS; MACROLIDES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; THIONES;

EID: 19244376064     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00133-4     Document Type: Article

References (10)

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3. (c) Hirayama, N. Matsuzawa, E. S. Chem. Lett. 1993, 1957.
4. 2. (a) Hara, M.; Saitoh, Y.; Nakano, H. Biochemistry 1990, 29, 5676.
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6. 3. Oxidative DNA cleavage by leinamycin in addition to the DNA alkylation was recently reported. Mitra, K.; Kim, W.; Daniels, J. S.; Gates, K. S. J. Am. Chem. Soc. 1997, 119, 11691.
7. 4. For our synthetic approach, see: (a) Kanda, Y; Saito, H.; Fukuyama, T. Tetrahedron Lett. 1992, 33, 5701.
8. (b) Kanda, Y.; Fukuyama, T. J. Am. Chem. Soc. 1993, 115, 8451.
9. + 595.1606, found 595.1606.
10. 6. Each isomer at the C=N double bond was isolated in case of 9b and 9c. The stereochemistry was determined by NMR spectra. For the determination of oxime stereochemistry, see: Gasc, J.-C.; Gouin D'Ambrieres, S.; Lutz, A.; Chantot, J.-F. J. Antibiotics 1991, 44, 313.