69299-74-7

Usage

InChI:InChI=1/C29H31NO12/c1-11-24(34)15(30-12(2)32)7-19(41-11)42-17-9-29(39,18(33)10-31)8-14-21(17)28(38)23-22(26(14)36)25(35)13-5-4-6-16(40-3)20(13)27(23)37/h4-6,11,15,17,19,24,31,34,36,38-39H,7-10H2,1-3H3,(H,30,32)/t11-,15-,17-,19-,24+,29-/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 56420-45-2 epirubicin Hydrochloride 
• 23214-92-8 doxorubicin 
• 64-19-7 acetic acid 

Relevant academic research and scientific papers

Fatty acyl amide derivatives of doxorubicin: Synthesis and in vitro anticancer activities

Doxorubicin is extensively used in anticancer therapy. Doxorubicin is highly hydrophilic, has short half-life, and its use is associated with severe side effects at high doses. Fatty acyl amide derivatives of doxorubicin were synthesized with the expectation to improve the lipophilicity and anticancer activity of the drug. The lipophilicity was enhanced with the increase in chain length of fatty acyl moiety. Conjugation of 4′-amino group with fatty acids through an amide bond reduced the anticancer activity in leukemia, breast, ovarian, and colon cancer cell lines, suggesting that the presence of free amino group is required for anticancer activity of doxorubicin. Dodecanoyl-doxorubicin derivative was consistently the most effective among the synthesized derivatives and inhibited the proliferation of colon (HT-29) and ovarian (SK-OV-3) cancer cells by 64% and 58%, respectively, at a concentration of 1 μM after 96 h incubation.

NEW DERIVATIVES OF EPIRUBICIN, THEIR MEDICINAL APPLICATION AND PHARMACEUTICALS ACCEPTABLE FORMS OF DRUGS

New derivatives of 7-O-(3'amino-2',3',6'-trideoxy-α,β,L- arabinoheksopiranosyl)-adriamycinone (epirubicin) presented at Formula 1, where R1, R2, R3 and R4 are the same and indicate hydrogen atom, alkyl group, isopropyl, alkenyl or alkinyl, especially acetyl or alkylcarbonyl group, all with alkyl chain containing 1 to 5 carbon atoms or dimethylformamidinyl group, at which if R1 and R4 indicate simultaneously hydrogen atom, then R3 indicates dimethylformamidinyl group. According to the invention, medical application of novel epirubicin derivatives is characterized by the fact, that derivatives presented at Formula 1 are used as active substances potently inhibiting hepatitis C virus (HCV) replication. Pharmaceutically acceptable form of the drug against hepatitis C virus (HCV) infections as active substance contains epirubicin derivatives presented at Formula (1), where R1, R2, R3 and R4 have above mentioned indications, eventually in the form of hydrochloride. According to invention, form of the drug ensures simultaneously low toxicity in Huh 7 and PBMC cells, therapeutic index (TI) better than for epirubicin, and lower than for epirubicin acute toxicity in vivo.

NEW DERIVATIVES OF EPIRUBICIN, THEIR MEDICINAL APPLICATION AND PHARMACEUTICALY ACCEPTABLE FORMS OF DRUGS

The present invention relates to novel derivatives of epirubicin, pharmaceutical composition comprising these derivatives, and uses of epirubicin and its derivative for treating HCV.