• Bulletin of the Korean Chemical Society
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• v.27 no.9
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• pp.1359-1363
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• 2006

Novel anthracycline analogues 2-9 as potential anticancer agents were synthesized from daunomycin (1a) and doxorubicin (1b). Compounds 2, 6, and 7 were prepared by the nucleophilic displacement type esterification of a 14-bromodaunomycin (1c) with a sodium lactate, and stearic acid, respectively. Compounds 3-5 and 7-9 were prepared by the reaction of either daunomycin (1a) or doxorubicin (1b) with L-lactic and stearic acids in the presence of EDCI/PP reagents.

• Bulletin of the Korean Chemical Society
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• v.22 no.6
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• pp.581-586
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• 2001

The potential anticancer agents, new anthracycline analogues (2-9) have been synthesized from the glycosides daunomycin (1a) and doxorubicin (1b). Compounds 2 and 6 were prepared by nucleophilic displacement esterification of a 14-bromodauomycin(1c) with sodium or potassium salts of butyric and all trans retinoic acid, respectively. Compounds 3 and 7 were obtained from daunomycin (1a) by direct amidation with a butyric and all trans retinoic acid in the presence of EDCI and PP, respectively. Compounds 4 and 8 were obtained from doxorubicin (1b) by reaction with the corresponding acids in the same manner. Compounds 5 and 9 were prepared from doxorubicin (1b) by acylation with two equivalents of the corresponding acids under the same reaction conditions.

• Journal of the Korean Chemical Society
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• v.34 no.5
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• pp.465-468
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• 1990

7-Deoxy-9-methyl aklavinones, the derivatives of aklavinone (the aglycone of extensive family of glycosidically derived from anthracycline antibiotics possessing significant activity), were synthesized by the simple and efficient reaction procedure.

• Bulletin of the Korean Chemical Society
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• v.22 no.6
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• pp.587-592
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• 2001

The potential anticancer agents new anthracycline derivatives (2~9) have been synthesized from daunomycin (1a) and doxorubicin (1b) ad starting materials. Compounds 2 and 6 were prepared by the nucleophilic displacement type esterification of a 14-bromodaunomycin (1c) with a acetylsalicylic and palmitic acid in triethylamine, respectively. Compound 3 and 7 were obtained from daunomycin (1a) by direct amidation with the corresponding acids in the presence of EDCI and PP as esterification regents. Whereas 4 and 8 were prepared by reaction of doxorubicin (1b) with one equivalent of acetylsalicylic and palmitic acid using DCC/DMAP, respectively, 5 and 9 were obtained from 1b by acylation with two equivalents of the corresponding acids using EDCI/PP reagents.

• YAKHAK HOEJI
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• v.41 no.6
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• pp.718-723
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• 1997

In the course of developing novel antitumor intercalating agents, we synthesized 3- carbamoyloxymethyl-azaanthraquinones 6-12, incorporating the latent alkylating functionality. These compounds were designed to explore the effect of heteroatom incorporation into anthraquinone chromophore and the effect of the incorporation of the latent alkylating functionality. The derivatives were prepared by hetero Diels-Alder reaction as a key step followed by functionality of allylic methyl to the desired substituents. Growth inhibitory studies of the azaanthraquinones were conducted in vitro against human cancer cell lines (SNU-354: liver and MCF7: breast) and human epidermoid carcinoma cells that are sensitive (KB-3-1) and multidrug-resistant (KB-V-1). The derivatives were 10 to 100-fold less potent than doxorubicin against sensitive cell lines. However, they were marginally cross-resistant with doxorubicin against KB-V-1.

• 한국생물공학회:학술대회논문집
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• 2003.04a
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• pp.533-538
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• 2003

To establish an effective and reliable technique of mutation by protoplast regeneration in doxorubicin overproducing industrial strain, it is essential to optimize the conditions for protoplast regeneration. $CaCO_3$ as buffer, the negative effect of glucose was still evident without significant changes in pH, ruling out acidity as responsible for the suppression of anthracycline production and suggesting a direct effect of glucose on antibiotic biosynthesis. Production of doxorubicin was improved in doxorubicin overproducing industrial strain (BR-Dox) when protoplast regenerated. BR-Dox4 and BR-Dox6 of BR-Dox derivatives improved doxorubicin production by 25.2 % and 12.2 %, respectively.

• YAKHAK HOEJI
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• v.40 no.2
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• pp.117-125
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• 1996

3'-Deamino-3-hydroxy-4'-fluoro- or 3'-deamino-3'-hydroxy-4'-azido-daunorubicin(6,8) and -doxorubicin(7,9) have been synthesized, respectively. Compounds 7,8 and 9 were mo re cytotoxic than daunorubicin(1) and doxorubicin(2) against L1210 murine leukemic cell in vitro. When administered intraperitoneally for 9 days starting 1 day after tumor inoculation, compounds 7(T/C 605%) and 9(T/C 488%) showed significant antitumor activity for ip-inoculuated L1210 murine leukemia at wide range of doses.

• YAKHAK HOEJI
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• v.40 no.1
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• pp.10-18
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• 1996

Daunirubicin and doxorubicin analogues (5,7,8,9,) in which the natural amino sugar, daunosamine, is replaced by rhamnopyranosyl or 4'-amino rhamnopyranosyl residues have been p repared. The in vitro cytotoxicity of compound 5 or 7 was similar to that of doxorubicin for P388 murine leukemic cell line. But compound 8 or 9 was less cytotoxic than doxorubicin. When administered intravenously on day 1, compound 9 showed antitumor activity comparable to that of doxorubicin against ip-inoculated L1210 murine leukemia and found to be less toxic than doxorubicin. But the in vivo antitumor activity of compound 7 or 8 was inferior to that of doxorubicin.