10-Hydroxycamptothecin

• Catalog No.: Bio-0126
• CAS Number: 19685-09-7
• M. F.: C20H16N2O5
• M. W.: 364.35144

SYNONYMS

• IUPAC name: 19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• IUPAC Traditional name: 19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• Synonyms: Camptothecin

DATABASE IDS

• CAS Number: 19685-09-7

PROPERTIES

• Application(s): Used in cancer chemotherapy
• Biological Source: Minor alkaloid from Camptotheca acuminata (Nyssaceae)
• Mechanism of Action: Inhibitor of DNA enzyme topoisomerase I

REFERENCES

• Wall, M.E. et al., J.A.C.S., 1966, 88, 3888, (isol, uv, ir, pmr, cryst struct)
• Wani, M.C. et al., J.O.C., 1969, 34, 1364, (isol, uv, ir, pmr, struct, 10-Hydroxycamptothecin, 10-Methoxycamptothecin)
• Volkmann, R. et al., J.A.C.S., 1971, 93, 5576, (synth)
• Winterfeldt, E. et al., Angew. Chem., Int. Ed., 1972, 11, 289, (synth)
• Boch, M. et al., Chem. Ber., 1972, 105, 2126, (synth)
• Tang, C. et al., J.A.C.S., 1972, 94, 8615, (synth, uv)
• Schultz, A.G., Chem. Rev., 1973, 73, 385, (rev)
• Sugasawa, T. et al., Chem. Pharm. Bull., 1974, 22, 77, (synth, ir, pmr)
• Tang, C.S.F. et al., J.A.C.S., 1975, 97, 159, (synth, uv, pmr)
• Bradley, J.C. et al., J.O.C., 1976, 41, 699, (synth)
• Sheriha, G.M. et al., Phytochemistry, 1976, 15, 505, (biosynth)
• Heckendorf, A.H. et al., Tet. Lett., 1977, 4153, (biosynth)
• Wani, M.C. et al., J. Med. Chem., 1980, 23, 554, (synth, 20-Deoxycamptothecin, 10-Hydroxycamptothecin, 10-Methoxycamptothecin)
• Hutchinson, C.R., Tetrahedron, 1981, 37, 1047, (rev)
• Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 12515
• Cai, J.-C. et al., Alkaloids (N.Y.), 1983, 21, 101, (rev, pharmacol)
• Earl, R.A., J.A.C.S., 1983, 105, 6991, (synth)
• Ihara, M. et al., J.O.C., 1983, 48, 3150, (synth)
• Earl, R.A. et al., J.O.C., 1984, 49, 4786, (synth)
• Suffness, M. et al., Alkaloids (N.Y.), 1985, 25, 83, (antineoplastic activity)
• Wall, M.E. et al., J. Med. Chem., 1986, 29, 1553, (10-Hydroxycamptothecin)
• Lin, L.-Z. et al., J. Nat. Prod., 1990, 53, 186, (cmr, Camptothecin, 10-Hydroxycamptothecin)
• Ejima, X. et al., J.C.S. Perkin 1, 1990, 27, (synth)
• Priel, E., AIDS Res. Hum. Retroviruses, 1991, 7, 65, (anti-HIV activity)
• Ezell, E.L. et al., J. Nat. Prod., 1991, 54, 1645, (pmr, cmr)
• Curran, D.P. et al., J.A.C.S., 1992, 114, 5863, (synth)
• Comins, D.L. et al., J.A.C.S., 1992, 114, 10971, (synth)
• Wall, M.E., Chron. Drug Discovery, 1993, 3, 327, (rev)
• Beijnen, J.H. et al., J. Chromatogr., 1993, 617, 111, (hplc)
• Shen, W. et al., J.O.C., 1993, 58, 611, (synth)
• Comins, D.L. et al., J.O.C., 1994, 59, 5120, (synth)
• Fang, F.G. et al., J.O.C., 1994, 59, 6142, (synth)
• Rao, A.V.R. et al., Tet. Lett., 1994, 35, 3613, (synth)
• Camptothecins, (eds. Potmesil, M. et al), CRC Press, 1995, (book)
• Wall, M.E. et al., Cancer Res., 1995, 55, 753, (rev)
• Bodley, A.L. et al., Proc. Natl. Acad. Sci. U.S.A., 1995, 92, 3726
• Jew, A. et al., Tetrahedron: Asymmetry, 1995, 6, 1245, (synth)
• Murata, N. et al., Synlett, 1997, 298-300, (synth)
• Ciufolini, M.A. et al., Tetrahedron, 1997, 53, 11049, (synth, bibl)
• Wall, M.E. et al., Alkaloids (London), 1998, 50, 509-536, (rev)
• Chavan, S.P. et al., Tet. Lett., 1998, 39, 6745-6748, (synth)
• Tagami, K. et al., Heterocycles, 2000, 53, 771-775, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CBB870; CBB875