TY - JOUR
T1 - Structure-activity relationships of elloramycin and tetracenomycin C
AU - Rohr, Jürgen
AU - Zeeck, Axel
PY - 1990
Y1 - 1990
N2 - The structure-activity relationships of the anthracycline-related antibiotics of the tetracenomycin C/elloramycin-type were investigated by derivatization of elloramycin (1) and elloramycinone (2). During hydrolysis experiments a unique transglycosylation reaction was discovered, converting elloramycin (1) into isoelloramycin (10) by treatment with anhydrous trifluoroacetic acid. Following the proposed structure-activity relationship concept, 8-O-methylelloramycinone (14) was synthesized from elloramycinone (2), and was shown to be the most active derivative according to the proliferation inhibition assay against murine L1210 leukemia cells.
AB - The structure-activity relationships of the anthracycline-related antibiotics of the tetracenomycin C/elloramycin-type were investigated by derivatization of elloramycin (1) and elloramycinone (2). During hydrolysis experiments a unique transglycosylation reaction was discovered, converting elloramycin (1) into isoelloramycin (10) by treatment with anhydrous trifluoroacetic acid. Following the proposed structure-activity relationship concept, 8-O-methylelloramycinone (14) was synthesized from elloramycinone (2), and was shown to be the most active derivative according to the proliferation inhibition assay against murine L1210 leukemia cells.
UR - http://www.scopus.com/inward/record.url?scp=0025103761&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0025103761&partnerID=8YFLogxK
U2 - 10.7164/antibiotics.43.1169
DO - 10.7164/antibiotics.43.1169
M3 - Article
C2 - 2211379
AN - SCOPUS:0025103761
SN - 0021-8820
VL - 43
SP - 1169
EP - 1178
JO - Journal of Antibiotics
JF - Journal of Antibiotics
IS - 9
ER -