Synthesis,Crystal Structure and Anticoagulant Activity of 5-Chloro-N-[[(5S)-2-oxo-3-[4-(2-oxopyridin-1(2H)-yl)phenyl]oxazolidin-5-yl]methyl]thiophene-2-carboxamide  

作　　者：刘巍 袁静 张士俊 徐为人 黄长江 汤立达 

机构地区：[1]Tianjin Key Laboratory of Molecular Design and Drug Discovery,Tianjin Institute of Pharmaceutical Research

出　　处：《Chinese Journal of Structural Chemistry》2014年第7期1091-1095,共5页结构化学（英文）

基　　金：Supported by Key Projects of Tianjin Science and Technology Support Plan(12ZCZDSY01100)

摘　　要：The title compound （zifaxaban 2, C20HI6C1N3O4S, Mr = 429.87） was synthesized and its crystal structure was determined by single-crystal X-ray diffraction. Zifaxaban crystallizes in monoclinic, space group P21 with a = 5.7900（12）, b = 13.086（3）, c = 12.889（3） A, β= 100.86（3）°, V = 959.1（3） ）k3, Z = 2, Dc= 1.489 g/cm3, F（000） = 444,μ= 0.342 mm-l, the final R = 0.0320 and wR = 0.0640 for 2717 observed reflections （I 〉 20（I）. The absolute configuration of the stereogenic center in the title compound was confirmed to be S by single-crystal X-ray diffraction. Four existing intermolecular hydrogen bonds help to stabilize the lattice and the molecule in the lattice to adopt an L-shape conformation. Zifaxaban was slightly more active than rivaroxaban 1 in in vitro assay against human FXa and therefore is promising as a drug candidate.The title compound （zifaxaban 2, C20HI6C1N3O4S, Mr = 429.87） was synthesized and its crystal structure was determined by single-crystal X-ray diffraction. Zifaxaban crystallizes in monoclinic, space group P21 with a = 5.7900（12）, b = 13.086（3）, c = 12.889（3） A, β= 100.86（3）°, V = 959.1（3） ）k3, Z = 2, Dc= 1.489 g/cm3, F（000） = 444,μ= 0.342 mm-l, the final R = 0.0320 and wR = 0.0640 for 2717 observed reflections （I 〉 20（I）. The absolute configuration of the stereogenic center in the title compound was confirmed to be S by single-crystal X-ray diffraction. Four existing intermolecular hydrogen bonds help to stabilize the lattice and the molecule in the lattice to adopt an L-shape conformation. Zifaxaban was slightly more active than rivaroxaban 1 in in vitro assay against human FXa and therefore is promising as a drug candidate.

关 键 词：SYNTHESIS crystal structure OXAZOLIDINONE factor Xa inhibitor zifaxaban 

分 类 号：O641.3[理学—物理化学]