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2004
Anthracene derivatives
Q 1080
Synthesis and Cytotoxic Evaluation of Two Novel Anthraquinone Derivatives. —
and aminohexanoic acid are incorporated as specific side arms in the synthesis
45- 116 L-Serine
of anthraquinone derivatives (IX) and (XI). The side arms, weakly related to ametantrone side chains, are not only able to form hydrogenic or covalent bonds with DNA base
pairs, but also possess nucleophilic groups to intercalate more easily with DNA three
dimensional structures. Carrying out the synthesis of the anthraquinone backbone by
Friedel—Crafts intramolecular cyclization in the presence of H3BO 3 and conc. H2SO4
instead of AlCl3 increases the yield and reduces the reaction time. Higher yields of the
final products in the amidation step can also be achieved by using ethyl chloroformate
as coupling agent. Compounds (IX) and (XI) are cytotoxic in micromolar concentrations, although they are almost as effective as the control doxorubicin against a panel
of cancer cell lines. — (SADEGHI-ALIABADI*, H.; TABARZADI, M.; ZARGHI,
A.; Farmaco 59 (2004) 8, 645-649; Dep. Pharm. Chem., Fac. Pharm. Pharm. Sci.,
Isfahan Univ. Med. Sci., Isfahan, Iran; Eng.) — H. Hoennerscheid
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