Synthesis of methyl bacteriopheophorbide-d with 8-propyl group

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 11, 1997, Pages 1415-1418

  Tamiaki, Hitoshi ^a   Tomida, Taro ^a   Miyatake, Tomohiro ^a  

^a RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUP; PHEOPHORBIDE;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030973069     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00231-X     Document Type: Article

References (16)

1. A recent review: Tamiaki, H. Coord. Chem. Rev. 1996, 148, 183-197.
2. Smith, K. M.; Goff, D. A. J. Chem. Soc., Perkin Trans. 1 1985, 1009-1113.
3. Smith, K. M.; Bisset, G. M. F.; Bushell, M. J. J. Org. Chem. 1980, 45, 2218-2224.
4. One attempt to prepare petroporphyrin analogues with several 8-alkyl groups was proposed: Atkinsoh, E. J.; Clezy, P. S.; Leung, C. W. F.; Ramadan, S.; Salek, A.; Zhuo, M. Aust. J. Chem. 1995, 48, 1873-1885.
5. Tamiaki, H.; Amakawa, M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99.
6. Tamiaki, H.; Miyatake, T.; Tanikaga, R. Tetrahedron Lett. 1997, 38, 267-270.
7. Chang, C. K.; Sotiriou, C. J. Org. Chem. 1987, 52, 926-929. Pandey, R. K.; Constantine, S. C.; Goff, D. A.; Kozyrev, A. N.; Dougherty, T. J.; Smith, K. M. Bioorg. Med. Chem. Lett. 1996, 6, 105-110.
8. Chang, C. K.; Sotiriou, C. J. Org. Chem. 1987, 52, 926-929. Pandey, R. K.; Constantine, S. C.; Goff, D. A.; Kozyrev, A. N.; Dougherty, T. J.; Smith, K. M. Bioorg. Med. Chem. Lett. 1996, 6, 105-110.
9. Compound 5 has already been synthesized by other procedures: Inhoffen, H. H.; Jäger, P.; Mählhop, R.; Mengler, C.-D. Liebigs Ann. Chem. 1967, 704, 188-207. Also, similar 8-vinylchlorins were recently prepared: Gerlach, B.; Smith, K. M. Tetrahedron Lett. 1996, 37, 5431-5434; Zheng, G.; Kozyrev. A. N.; Dougherty, T. J.; Smith, K. M.; Pandey, R. K., Chem. Lett. 1996, 1119-1120.
10. Compound 5 has already been synthesized by other procedures: Inhoffen, H. H.; Jäger, P.; Mählhop, R.; Mengler, C.-D. Liebigs Ann. Chem. 1967, 704, 188-207. Also, similar 8-vinylchlorins were recently prepared: Gerlach, B.; Smith, K. M. Tetrahedron Lett. 1996, 37, 5431-5434; Zheng, G.; Kozyrev. A. N.; Dougherty, T. J.; Smith, K. M.; Pandey, R. K., Chem. Lett. 1996, 1119-1120.
11. Compound 5 has already been synthesized by other procedures: Inhoffen, H. H.; Jäger, P.; Mählhop, R.; Mengler, C.-D. Liebigs Ann. Chem. 1967, 704, 188-207. Also, similar 8-vinylchlorins were recently prepared: Gerlach, B.; Smith, K. M. Tetrahedron Lett. 1996, 37, 5431-5434; Zheng, G.; Kozyrev. A. N.; Dougherty, T. J.; Smith, K. M.; Pandey, R. K., Chem. Lett. 1996, 1119-1120.
12. Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421-12432.
13. Tamiaki, H.; Shimono, Y.; Rattray, A. G. M.; Tanikaga, R. Bioorg. Med. Chem. Lett. 1996, 6, 2085-2086.
14. 1H-NMR, VIS, IR and/or MS spectra.
15. 1-epimerically pure zinc methyl 8-Et-12-Me-BPhe-d) was investigated: Tamiaki, H.; Takeuchi, S.; Tanikaga, R.; Balaban, S. T.; Holzwarth, A. R.; Schaffner, K. Chem. Lett. 1994, 401-402. Balaban, T. S.; Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. B 1997, 101, in press.
16. 1-epimerically pure zinc methyl 8-Et-12-Me-BPhe-d) was investigated: Tamiaki, H.; Takeuchi, S.; Tanikaga, R.; Balaban, S. T.; Holzwarth, A. R.; Schaffner, K. Chem. Lett. 1994, 401-402. Balaban, T. S.; Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. B 1997, 101, in press.