The structure of a biological alkylating agent with antiumor properties: N-{2-[(chloroethyl)thio]ethyl}-10-methyl-9-anthracenemethylamine hydrochloride and of its selfalkylation product 10-methyl-9-[(4-thiomorpholino)methyl]anthracene

摘要: The structures of a biological alkylating agent, N{ 2-[ (2-chloroethyl)thio ]ethyl }- 10-methyl-9-anthracenemethylamine hydrochloride (I), with antitumor properties, and its self-alkylation product, 10-methyl9-[(4-thiomorpholino)methyl]anthracene (II), have been determined. Crystal data for (I) are C20H23CINS +. Cl-, M r = 380.38, 22.748 (2), b 13.007 (1), c 6.3443 (8) A, V= 1877.2 (4) A 3, D C 1.35 Mg m -3, space group P21212 ~, Z 4. (II) C20H2~NS, 307.46, 35.816 (6), 6.8965 (9), 13.895 (2) fl= 105.89 (1) °, 3300.9 (8)/k s, Dc 1.24 P21/a, 8 (2 molecules per asymmetric unit). final R values were 0.050 1220 observed 0.047 4513 (II). In the agent there is no internal NH... S hydrogen bond in side chain, unlike case other ICR compounds which acridine agents intramolecular NH...N bonds their chains. This lack bonding may facilitate process. flexibility anthracene ring system shown by variability angle between planes two outer rings as these structures. both systems do not overlap 3.4 apart, but they lie parallel planes, approximately 3.5 remarkably similar motif each.