TY - JOUR
T1 - Synthesis of aminoanthraquinone derivatives and their in vitro evaluation as potential anti-cancer drugs
AU - Katzhendler, Jehoshua
AU - Gean, Keria Fiorella
AU - Bar-Ad, Gidon
AU - Tashma, Zeev
AU - Ben-Shoshan, Raphael
AU - Ringel, Israel
AU - Bachrach, Uriel
AU - Ramu, Avner
PY - 1989
Y1 - 1989
N2 - Anthraquinones, monosubstituted by aminoalkylamino side chains at positions 1, 2 or disubstituted at positions 1, 5 or 1, 8 were prepared. Their in vitro cytotoxic activity (ED50) was evaluated using: 1) P388 murine leukemia cells and 2) a subline of these cells resistant to doxorubicin (P388/ADR). The results of the structure-activity relationship analysis indicated that monosubstitution in position 1 or 2 showed a decrease of the activity when compared to adryamicin. Disubstitution in positions 1, 5 by N,N-dimethyl ethylenediamine side chain led to optimal activity, whereas the presence of cyclic dialkylamino substituents in the same positions resulted in a corresponding decrease in the anti-tumor activity. Disubstitution in positions 1,8 did not show any improvement in the cytotoxic activity.
AB - Anthraquinones, monosubstituted by aminoalkylamino side chains at positions 1, 2 or disubstituted at positions 1, 5 or 1, 8 were prepared. Their in vitro cytotoxic activity (ED50) was evaluated using: 1) P388 murine leukemia cells and 2) a subline of these cells resistant to doxorubicin (P388/ADR). The results of the structure-activity relationship analysis indicated that monosubstitution in position 1 or 2 showed a decrease of the activity when compared to adryamicin. Disubstitution in positions 1, 5 by N,N-dimethyl ethylenediamine side chain led to optimal activity, whereas the presence of cyclic dialkylamino substituents in the same positions resulted in a corresponding decrease in the anti-tumor activity. Disubstitution in positions 1,8 did not show any improvement in the cytotoxic activity.
KW - aminoantraquinones
KW - anti-cancer
KW - DNA
KW - intercalation
UR - http://www.scopus.com/inward/record.url?scp=0024578824&partnerID=8YFLogxK
U2 - 10.1016/0223-5234(89)90159-1
DO - 10.1016/0223-5234(89)90159-1
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AN - SCOPUS:0024578824
SN - 0223-5234
VL - 24
SP - 23
EP - 30
JO - European Journal of Medicinal Chemistry
JF - European Journal of Medicinal Chemistry
IS - 1
ER -