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. shu

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

1.
Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, China

Received Date: 7 January 2014
Available Online: 20 May 2014
Fund Project:

The title compound (zifaxaban 2, C₂₀H₁₆ClN₃O₄S, M_r=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, D_c=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.
- synthesis,
- crystal structure,
- oxazolidinone,
- factor Xa inhibitor,
- zifaxaban
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