CAS 119288-23-2

7(O)-(3-amino-2,3,6-trideoxy-2-fluorotalopyranosyl)adriamycinone

Description:

7(O)-(3-amino-2,3,6-trideoxy-2-fluorotalopyranosyl)adriamycinone, identified by its CAS number 119288-23-2, is a derivative of adriamycin, a well-known anthracycline antibiotic used in cancer therapy. This compound features a modified sugar moiety, specifically a 3-amino-2,3,6-trideoxy-2-fluorotalopyranosyl group, which enhances its pharmacological properties. The presence of the amino group may contribute to increased solubility and improved interaction with biological targets, while the fluorine substitution can influence the compound's stability and reactivity. The structural modifications aim to optimize the drug's efficacy and reduce potential side effects associated with traditional adriamycin. As with other anthracyclines, this compound likely exhibits mechanisms of action that include intercalation into DNA and inhibition of topoisomerase II, leading to disruption of DNA replication and transcription in rapidly dividing cancer cells. Further studies would be necessary to fully elucidate its biological activity, therapeutic potential, and safety profile in clinical applications.

Formula: C₂₇H₂₉ClFNO₁₁

InChI: InChI=1/C27H28FNO11.ClH/c1-9-21(32)20(29)19(28)26(39-9)40-13-7-27(37,14(31)8-30)6-11-16(13)25(36)18-17(23(11)34)22(33)10-4-3-5-12(38-2)15(10)24(18)35;/h3-5,9,13,19-21,26,30,32,34,36-37H,6-8,29H2,1-2H3;1H/t9-,13-,19+,20-,21+,26-,27-;/m0./s1

Synonyms:

• 7(O)-(3-Amino-2,3,6-trideoxy-2-fluoro-alpha-L-talopyranosyl)adriamycinone
• 7-Atfta
• 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-2-fluoro-alpha-L-talopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S-cis)-
• (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-2-fluoro-alpha-L-talopyranoside hydrochloride
• 7(O)-(3-Amino-2,3,6-trideoxy-2-fluorotalopyranosyl)adriamycinone