CAS 103946-11-8

7-O-(2,6-dideoxy-2-fluorotalopyranosyl)daunomycinone

Description:

7-O-(2,6-Dideoxy-2-fluorotalopyranosyl)daunomycinone is a complex chemical compound derived from daunomycinone, which is an anthracycline antibiotic known for its anticancer properties. This specific derivative features a sugar moiety, 2,6-dideoxy-2-fluorotalopyranosyl, attached at the 7-position of the daunomycinone structure. The presence of the fluorine atom in the sugar moiety may influence the compound's biological activity and pharmacokinetics, potentially enhancing its therapeutic efficacy or altering its interaction with biological targets. The compound is characterized by its unique structural features, which include a chromophore system typical of anthracyclines, contributing to its ability to intercalate DNA and inhibit topoisomerase II, leading to cytotoxic effects in cancer cells. Additionally, the modification with the sugar moiety can affect solubility, stability, and cellular uptake. Overall, this compound represents a significant area of research in medicinal chemistry, particularly in the development of targeted cancer therapies.

Formula: C₂₇H₂₇FO₁₁

InChI: InChI=1/C27H27FO11/c1-9-20(30)25(35)19(28)26(38-9)39-14-8-27(36,10(2)29)7-12-16(14)24(34)18-17(22(12)32)21(31)11-5-4-6-13(37-3)15(11)23(18)33/h4-6,9,14,19-20,25-26,30,32,34-36H,7-8H2,1-3H3/t9-,14-,19+,20+,25-,26-,27-/m0/s1

Synonyms:

• Dftd
• 5,12-Naphthacenedione, 8-acetyl-10-((2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S-cis)-
• (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,6-dideoxy-2-fluoro-alpha-L-talopyranoside
• 7-O-(2,6-Dideoxy-2-fluorotalopyranosyl)daunomycinone
• (7S,9S)-9-acetyl-7-[(2R,3R,4R,5S,6S)-3-fluoro-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• 5,12-Naphthacenedione, 8-acetyl-10-[(2,6-dideoxy-2-fluoro-α-L-talopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S-cis)- (9CI)