Synthesis and reactivity of some chiral, nonracemic 1- azabicyclo[4.1.0]heptanes related to the azinomycins

Tetrahedron

Volumn 54, Issue 22, 1998, Pages 6029-6034

  Hodgkinson, Timothy J ^a   Kelland, Lloyd R ^b   Shipman, Michael ^a   Vile, Julia ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZINOMYCIN; QUINUCLIDINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHIRALITY; CYTOTOXICITY; DNA ALKYLATION; DNA REPLICATION; DRUG SYNTHESIS; ENANTIOMER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

EID: 0032575241     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00283-X     Document Type: Article

References (13)

1. 1. (a) K. Nagaoka, M. Matsumoto, J. Ono, K. Yokoi, S. Ishizeki, and T. Nakashima, J. Antibiot., 1986, 39, 1527;
2. (b) K. Yokoi, K. Nagaoka, and T. Nakashima, Chem. Pharm. Bull., 1986, 34, 4554;
3. (c) S. Ishizeki, M. Ohtsuka, K. Irinoda, K.-I. Kukita, K. Nagaoka, and T. Nakashima, J. Antibiot., 1987, 40, 60.
4. 2. Azinomycin B has been shown to be identical to carzinophilin whose structure had previously been incorrectly assigned; see E.J. Moran and R.W. Armstrong, Tetrahedron Lett., 1991, 32, 3807.
5. 3. R.W. Armstrong, M.E. Salvati, and M. Nguyen, J. Am. Chem. Soc., 1992, 114, 3144.
6. 4. Azinomycin B / carzinophilin is highly unstable, see H. Kamada, S. Wakaki, Y. Fujimoto, K. Tomioka, S. Ueyama, H. Maruma, and K. Uzu, J. Antibiot., Ser. A, 1955, 8, 187.
7. 5. Azinomycin analogues containing the 1-azabicyclo[3.1.0]hexane ring system have been shown to be prone to ring opening in the presence of nucleophiles. See, for example (a) M. Hashimoto and S. Terishima, Heterocycles, 1998, 47, 59;
8. (b) M. Hashimoto, K. Yamada, and S. Terashima, Chem. Lett., 1992, 975.
9. 6. For other recent applications of 1-azabicyclo[4.1.0]heptanes in medicinal chemistry, see (a) M.K. Tong and B. Ganem, J. Am. Chem. Soc., 1988, 110, 312;
10. (b) B. Bernet, A.R.C. Bulusu Murty, and A. Vasella, Helv. Chim. Acta, 1990, 73, 940;
11. (c) H. Paulsen, M. Matzke, B. Orthen, R. Nuck, and W. Reutter, Liebigs Ann. Chem., 1990, 953;
12. (d) O.R. Martin, F. Xie, and L. Liu, Tetrahedron Lett., 1995, 36, 4027.
13. 7. T.J. Hodgkinson and M. Shipman, Synthesis, 1998, in press.