抗疟药α-(二正丁氨基甲基)-2,7-二氯-9-对氯亚苄基-4-芴甲醇的晶体和分子结构

CRYSTAL AND MOLECULAR STRUCTURE OF THE ANTIMALARIAL AGENT α-(DIBUTYLAMINOMETHYL)-2,7-DICHLORO-9-(p-CHLOROBENZYLIDENE)-4-FLUORENEMETHANOL(BENFLUMETOL)

摘要: 用X晶体衍射测定了氨基醇类抗疟药本芴醇( benflumetol I )的单晶结构,并与已知同类抗疟药金鸡纳生物碱进行了比较。再一次说明了氨基醇类化合物产生抗疟作用的三维空间结构特征。本芴醇的芴环平面与对氯苯基平面的二面角为52.8°。分子内 N-O 距离为2.709A,这一距离与金鸡纳生物碱分子内脂肪氮原子与氧原子之间距离相近。侧链中 N-C-C-O 的扭转角为47.6°。本芴醇单晶结构中存在分子内氢键,而未发现分子间氢键,这与以往认为产生抗疟作用的氨基醇类化合物存在分子间氢键而无分子内氢键不同。

Abstract: The three-dimensional crystal and molecular structure of benflumetol(I), α-(dibutylaminomethyl)-2,7-dichloro-9-(p-chlorobenzylidene)-4-fluorenemethanol, was determined by X-ray crystallography and compared with the crystal structures of the cinchona alkaloids. The aromatic rings of fluorene-phenyl system of benflumetol are twisted from each other by 52.8°. The torsion angle of N-C-C-O of benflumetol is 47.6°. The intramolecular aliphatic N-O distance in benflumetol is 2.709A, which is close to the N-O distance found in antimalarial cinchona alkaloids. Benflumetol contains an intramolecular hydrogen bond between the aliphatic nitrogen and oxygen atoms, no intermolecular hydrogen bond was found, which is different from the known amino alcohol antimalarials. 