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华法林和苯丙香豆素的异常旋光性质。

Anomalous chiroptical properties of warfarin and phenprocoumon.

作者信息

Valente E J, Trager W F

出版信息

J Med Chem. 1978 Jan;21(1):141-3. doi: 10.1021/jm00199a031.

DOI:10.1021/jm00199a031
PMID:619144
Abstract

The configurationally similar enantiomers of warfarin and phenprocoumon are found to exhibit circular dichroism curves which are nearly mirror related in the range of 240-340 nm. This effect is interpreted as being due to spatial similarities of the preferred conformations of opposite configurations of the two drugs in solution. An inherently dissymmetric chromophore (theta approximately 1.2 x 10(5)) is observed at approximately 220 nm for warfarin, the cyclic hemiketal tautomeric forms, and the cyclic methyl ketals.

摘要

华法林和苯丙香豆素的构型相似对映体在240 - 340纳米范围内呈现出近乎镜像相关的圆二色性曲线。这种效应被解释为是由于两种药物在溶液中相反构型的优选构象在空间上的相似性。对于华法林、环状半缩酮互变异构体和环状甲基缩酮,在约220纳米处观察到一个固有不对称发色团(θ约为1.2×10⁵)。

相似文献

1
Anomalous chiroptical properties of warfarin and phenprocoumon.华法林和苯丙香豆素的异常旋光性质。
J Med Chem. 1978 Jan;21(1):141-3. doi: 10.1021/jm00199a031.
2
Conformations of selected 3-substituted 4-hydroxycoumarins in solution by nuclear magnetic resonance. Warfarin and phenprocoumon.通过核磁共振确定溶液中选定的3-取代4-羟基香豆素的构象。华法林和苯丙香豆素。
J Med Chem. 1978 Feb;21(2):231-4. doi: 10.1021/jm00200a019.
3
Species differences of the stereoselective binding of phenprocoumon and warfarin enantiomers to serum albumins.苯丙香豆素和华法林对映体与血清白蛋白立体选择性结合的种属差异。
Comp Biochem Physiol C Comp Pharmacol. 1979;62C(1):101-5. doi: 10.1016/0306-4492(79)90107-2.
4
Optical studies on the mechanism of the interaction of the enantiomers of the antiocagulant drugs phenprocoumon and warfarin with human serum albumin.
Mol Pharmacol. 1977 Jan;13(1):70-9.
5
The preferred solution conformation of warfarin at the active site of cytochrome P-450 based on the CD spectra in octanol/water model system.基于正辛醇/水模型体系中的圆二色光谱,华法林在细胞色素P-450活性位点的优势溶液构象。
J Med Chem. 1984 Aug;27(8):1092-5. doi: 10.1021/jm00374a027.
6
Stereoselective metabolism of conformational analogues of warfarin by beta-naphthoflavone-inducible cytochrome P-450.β-萘黄酮诱导的细胞色素P-450对华法林构象类似物的立体选择性代谢
J Med Chem. 1985 Apr;28(4):503-6. doi: 10.1021/jm00382a021.
7
The effect of sulfinpyrazone on the disposition of pseudoracemic phenprocoumon in humans.磺吡酮对伪消旋苯丙香豆素在人体内处置的影响。
Clin Pharmacol Ther. 1987 Sep;42(3):312-9. doi: 10.1038/clpt.1987.154.
8
Structural forms of phenprocoumon and warfarin that are metabolized at the active site of CYP2C9.苯丙香豆素和华法林在CYP2C9活性位点代谢的结构形式。
Arch Biochem Biophys. 1999 Dec 1;372(1):16-28. doi: 10.1006/abbi.1999.1468.
9
Separation of the enantiomers of phenprocoumon and warfarin by high-performance liquid chromatography using a chiral stationary phase. Determination of the enantiomeric ratio of phenprocoumon in human plasma and urine.使用手性固定相通过高效液相色谱法分离苯丙香豆素和华法林的对映体。测定人血浆和尿液中苯丙香豆素的对映体比例。
J Chromatogr. 1989 Aug 25;493(1):149-56. doi: 10.1016/s0378-4347(00)82717-6.
10
Differential effect of the enantiomers of phenprocoumon and warfarin on the vitamin K1-epoxide/vitamin K1 ratio in rat plasma.苯丙香豆素和华法林对映体对大鼠血浆中维生素K1-环氧化物/维生素K1比值的差异影响。
J Pharm Pharmacol. 1979 Jul;31(7):490-1. doi: 10.1111/j.2042-7158.1979.tb13567.x.

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