Acridine derivatives. IV. Synthesis, molecular structure, and antitumor activity of the novel 9‐anilino‐2,3‐methylenedioxyacridines

Abstract

In the biological and physical investigation of a new class of deoxyribonucleic acid (DNA)‐intercalating antitumor agents, novel 9‐anilino‐2,3‐methylenedioxyacridines (twelve compounds) have been synthesized and evaluated for the activity against L1210 leukemia in vivo. A few of them possessed the same potency of the antitumor activity as 4′‐(9‐acridinylamino)methanesulfonyl‐m‐anisidine (amsacrine, m‐AMSA), which is an important antitumor agent in clinical use. The molecular structure of a typical one, 9a in this series have been determined by the X‐ray diffraction method using a single crystal. The results of this X‐ray investigation have shown that the new class of acridine derivatives have the methylenedioxy group fused at the 2‐ and 3‐positions of the acridine ring.

Synthesis, anticancer, anti-HIV-1, and antimicrobial activity of some tricyclic triazino and triazolo[4,3-e]purine derivatives

“…Oligo and polyribonucleotides containing selected triazolo [2,3-a] purines were moderately active against HIV but showed greater potency against human cyclomelagovirus (HCMV) than ganciclovir (Tutonda et al, 1998). These findings, together with the fact that the majority of DNA intercalating agents comprising a planar tricyclic or tetracyclic chromophore (Palmer et al, 1988;Filippatos et al, 1994;Kimura et al, 1992;Abadi et al, 1999), motivated our interest toward the design and synthesis of some triazino and triazolo [4,3-e] anticancer, antiviral and antimicrobial activities hoping to go a step forward in the field of antimetabolities. Two new series of substituted 6,8-dimethyl-1,4-dihydro-1,2,4-triazino[4,3-e]purine-7,9(6H, 8H)-diones 3; 4; 5 and 6a, b (Scheme 1) and 5,7,9-trimethyl-1,2,4-triazolo[4,3-e] purine-6,8(5H, 7H, 9H)-diones 11a-d; 12 and 13a-c (Scheme 2).…”

Synthesis and Structure-Activity Studies of Peptide-Acridine/Acridone Conjugates

“…The three-ring aromatic molecule is able to intercalate to nucleic acid and in consequence causes a disturbance in its synthesis [1][2][3][4][5]13,14].…”

“…The introduction of a new substitution to the motif of an appropriate molecule may have an influence on the activity of that compound. In the last few decades, acridines which are known as antitumor [1][2][3][4][5], antiviral [6][7][8], antiprion [9,10], antimicrobal [11], antiinflamatory and analgesic agents [12] have been in the center of interest of scientists. Those pharmaceutical properties have led scientists into modifying the acridine substitution pattern.…”

Ultrasonic irradiation of the ullmann condensation: Application to the preparation of dioxolo, dioxino, cyclopent, and imidazolo anthranilic acid derivatives

“…Scheme 1 To improve this method, we chose different acridine analogues already described with poor yields, and compared the classical Ullman-Jourdan condensation [6] with ultrasound. There are only few references on the synthesis of dioxolo [7], dioxino [8], cyclopent [9], and imidazolo acridine. In all these cases, the N-aryl anthranilic acids used as precursor for the synthesis of acridines are described with low yields.…”