ChemInform Abstract: Synthesis and Antitumor Activity of Fluorinated 1‐Aza and 1,8‐ Diazaanthraquinones.

Abstract

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Structure-Antitumor Activity Relationships of Aza- and Diaza-Anthracene-2,9,10-Triones and Their Partially Saturated Derivatives

“…The preparation and study of a number of semisynthetic analogues of DAQA (compounds 3 and 4 ) led Ōmura to the conclusion that the bis-lactam structure of the natural product was an essential requisite for thimidylate synthase inhibition and antitumor activity [ 30 ]. However, when we investigated the antitumor activity of a small set of derivatives of the structure 5 , we found that they exhibited good antitumor activities, particularly towards solid tumors [ 31 ], while the introduction of a fluorine atom at C-3 led to compounds with antileukemic activity [ 32 ]. In order to assist the establishment of structure–activity relationships within this class of compounds, we describe here a systematic study of the in vitro antitumor properties of a large series of derivatives of structure 5 , their 5,8-dihydro derivatives 6 , where one of the electron-withdrawing pyridine nitrogen atoms has been replaced by an electron-releasing enamine-like moiety, 1-azaanthraquinones derived from structure 7 related to the marcanines and more simplified structures such as quinolinedione derivatives 8 where the lactam scaffold that appears to be essential for cytotoxic activity is maintained ( Figure 2 ).…”