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CAS 72983-78-9

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5-Iminodaunorubicin

Description:
5-Iminodaunorubicin is an anthracycline derivative, primarily known for its application in cancer treatment. It is structurally related to daunorubicin, a well-known chemotherapeutic agent. This compound exhibits potent antitumor activity by intercalating into DNA, thereby disrupting the replication process and inhibiting topoisomerase II, an enzyme crucial for DNA unwinding. The presence of the imino group in its structure enhances its biological activity compared to its parent compound. 5-Iminodaunorubicin is characterized by its ability to induce apoptosis in cancer cells, making it a subject of interest in oncology research. Additionally, like other anthracyclines, it may exhibit cardiotoxicity, necessitating careful monitoring during treatment. Its solubility, stability, and pharmacokinetic properties are essential factors influencing its therapeutic efficacy and safety profile. Overall, 5-Iminodaunorubicin represents a significant compound in the development of targeted cancer therapies, with ongoing studies aimed at optimizing its use in clinical settings.
Formula:C27H30N2O9
InChI:InChI=1S/C27H30N2O9/c1-10-23(31)14(28)7-17(37-10)38-16-9-27(35,11(2)30)8-13-19(16)26(34)20-21(25(13)33)24(32)12-5-4-6-15(36-3)18(12)22(20)29/h4-6,10,14,16-17,23,29,31,33-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,23+,27-/m0/s1
InChI key:InChIKey=BLLIIPIJZPKUEG-HPTNQIKVSA-N
SMILES:OC=1C2=C([C@@H](O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C[C@@](C(C)=O)(O)C2)C(O)=C4C1C(=O)C=5C(C4=N)=C(OC)C=CC5
Synonyms:
  • 5(8H)-Naphthacenone, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-, (8S,10S)-
  • 5-Iminodaunomycin
  • NSC 254681
  • 5(8H)-Naphthacenone, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-, (8S-cis)-
  • (8S,10S)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,9,10,12-tetrahydro-6,8,11-trihydroxy-12-imino-1-methoxy-5(8H)-naphthacenone
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