Reaction #1366160

ord-3cbd80ce8cd84674aa1c2c0b9814bd84

Reaction equation

COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
Doxorubicin hydrochloride
O=C1c2ccccc2C(=O)c2cc3ccccc3cc21
5,12-Naphthacenedione
→
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
Doxorubicin

Reactants

—
DNA
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
Doxorubicin hydrochloride
O=C1c2ccccc2C(=O)c2cc3ccccc3cc21
5,12-Naphthacenedione
—
nucleic acid
—
(8s-cis)-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11 -trihydroxy-8-(hydroxyacetyl)-1-methoxy-hydrochloride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Doxorubicin hydrochloride, 5,12-Naphthacenedione, (8s-cis)-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11 -trihydroxy-8-(hydroxyacetyl)-1-methoxy-hydrochloride (hydroxydaunorubicin hydrochloride, Adriamycin) is used in a wide antineoplastic spectrum. It binds to DNA and inhibits nucleic acid synthesis, inhibits mitosis and promotes chromosomal aberrations.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06444872B1uspto-grants-2002_09