Citation:
LIU Wei, YUAN Jing, ZHANG Shi-Jun, XU Wei-Ren, HUANG Chang-Jiang, TANG Li-Da. 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[J]. Chinese Journal of Structural Chemistry,
2014, 33(7): 1091-1095.
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
摘要:
The title compound (zifaxaban 2, C20H16ClN3O4S, 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) Å, β=100.86(3)°, V=959.1(3) Å3, Z=2, Dc=1.489 g/cm3, F(000)=444, μ=0.342 mm-1, the final R=0.0320 and wR=0.0640 for 2717 observed reflections (I>2σ(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.
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关键词:
- synthesis
- / crystal structure
- / oxazolidinone
- / factor Xa inhibitor
- / zifaxaban
English
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
Abstract:
The title compound (zifaxaban 2, C20H16ClN3O4S, 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) Å, β=100.86(3)°, V=959.1(3) Å3, Z=2, Dc=1.489 g/cm3, F(000)=444, μ=0.342 mm-1, the final R=0.0320 and wR=0.0640 for 2717 observed reflections (I>2σ(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.
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Key words:
- synthesis
- / crystal structure
- / oxazolidinone
- / factor Xa inhibitor
- / zifaxaban
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