The synthesis of (R)-1-(2-oxocyclopentyliden)-2-alkanols and the (S)-forms, and their bio-antimutagenic activity against UV-induced Escherichia coli WP2 B/r Trp-

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 2, 1997, Pages 199-202

  Iriye, Ryozo ^a   Takai, Katsuki ^a   Noguchi, Masakazu ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ANTIMUTAGENIC AGENT;

ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; ENANTIOMER; ESCHERICHIA COLI; MUTATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET RADIATION;

EID: 0031021968     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00611-7     Document Type: Article

References (18)

1. T. Kada and H. Mochizuki, J. Radiat. Res., 22, 297-302 (1981).
2. K. Kakimuma, J. Koike, K. Kotani, N. Ikekawa, T. Kada and M. Nomoto, Agric. Biol Chem. (Tokyo), 48, 1905-1906 (1984).
3. K. Ishibashi, W. Takahashi, H. Takei, and K. Kakimuma, Agric. Biol Chem., 51, 1045-1049 (1987).
4. R. Iriye, K. Furukawa and M. Takeshita, Biosci. Biotech. Biochem. (Tokyo), 56, 512-513 (1992).
5. R. Iriye, A. Nakamura and M. Takeshita, Biosci. Biotech. Biochem. (Tokyo), 59, 401-407 (1995).
6. H. Sies, in •Oxidative Stress: Oxidants and Antioxidants•, ed. by H. Zollner, R. J. Schaur and H. Esterbauer, Academic Press, New York, 1991, p 337-369. H. Esterbauer, H. Zollner and R. J. Schaur, in •Membrane Lipids Oxidation• , Vol 1, CRC Press, Boca Raton, FL., 1990, p 239. H. Schauenstein, H. Esterbauer and H. Zollner, in •Aldehydes in Biological Systems; Their Natural Occurrence and Biological Activities•, Pion Ltd, London, 1977. Synthesis; S. Kang, K. Jung, J. Chung, E. Namkoong and T. Kim, J. Org. Chem., 60, 4678-4679 (1995).
7. H. Sies, in •Oxidative Stress: Oxidants and Antioxidants•, ed. by H. Zollner, R. J. Schaur and H. Esterbauer, Academic Press, New York, 1991, p 337-369. H. Esterbauer, H. Zollner and R. J. Schaur, in •Membrane Lipids Oxidation• , Vol 1, CRC Press, Boca Raton, FL., 1990, p 239. H. Schauenstein, H. Esterbauer and H. Zollner, in •Aldehydes in Biological Systems; Their Natural Occurrence and Biological Activities•, Pion Ltd, London, 1977. Synthesis; S. Kang, K. Jung, J. Chung, E. Namkoong and T. Kim, J. Org. Chem., 60, 4678-4679 (1995).
8. H. Sies, in •Oxidative Stress: Oxidants and Antioxidants•, ed. by H. Zollner, R. J. Schaur and H. Esterbauer, Academic Press, New York, 1991, p 337-369. H. Esterbauer, H. Zollner and R. J. Schaur, in •Membrane Lipids Oxidation• , Vol 1, CRC Press, Boca Raton, FL., 1990, p 239. H. Schauenstein, H. Esterbauer and H. Zollner, in •Aldehydes in Biological Systems; Their Natural Occurrence and Biological Activities•, Pion Ltd, London, 1977. Synthesis; S. Kang, K. Jung, J. Chung, E. Namkoong and T. Kim, J. Org. Chem., 60, 4678-4679 (1995).
9. H. Sies, in •Oxidative Stress: Oxidants and Antioxidants•, ed. by H. Zollner, R. J. Schaur and H. Esterbauer, Academic Press, New York, 1991, p 337-369. H. Esterbauer, H. Zollner and R. J. Schaur, in •Membrane Lipids Oxidation• , Vol 1, CRC Press, Boca Raton, FL., 1990, p 239. H. Schauenstein, H. Esterbauer and H. Zollner, in •Aldehydes in Biological Systems; Their Natural Occurrence and Biological Activities•, Pion Ltd, London, 1977. Synthesis; S. Kang, K. Jung, J. Chung, E. Namkoong and T. Kim, J. Org. Chem., 60, 4678-4679 (1995).
10. The reaction with use of excess amounts (1.5 equimols) of the sodium salt (5) (at 55°C for 16 hr) and with unsolubilization of the salt without preheating of the suspension caused the α-rearrangement reaction to yield 1-[(R)-O-MEMmandelyloxy]-2-octanone (12) in addition with 6s-a.
11. 2-3=10.1 & 2.7 Hz, 2 [76.35]), 5.26 (1H, s, mandelyl [76.67]), [170.81, COO], [222.87, CO].
12. The optically active 2-hydroxyalkanals have been prepared from (S)-aminoacids: M. Larcheveque and Y. Petit, bull. Soc. Chim. Fr., 1989, 130-139. H. Hagiwara, K. Kimura, and H. Uda, J. Chem. Soc., 1992, 693-700.
13. The optically active 2-hydroxyalkanals have been prepared from (S)-aminoacids: M. Larcheveque and Y. Petit, bull. Soc. Chim. Fr., 1989, 130-139. H. Hagiwara, K. Kimura, and H. Uda, J. Chem. Soc., 1992, 693-700.
14. 5).
15. 2 to form the epoxide with (1S,2S)-configuration. Formula presented
16. All new compounds showed reasonable precise MS spectra.
17. J. A. Dale and H. S. Mosher, J. Am, Chem. Soc., 95, 512-519 (1973).
18. 2-proton signals of each isomer were overlapped.