王智贤, 朱友成, 嵇汝运, 吕扬, 田之悦, 郑启泰. 羟甲芬太尼立体异构体的晶体结构J. 药学学报, 1994, 29(6): 433-437.
引用本文: 王智贤, 朱友成, 嵇汝运, 吕扬, 田之悦, 郑启泰. 羟甲芬太尼立体异构体的晶体结构J. 药学学报, 1994, 29(6): 433-437.
ZX Wang, YC Zhu, RY Ji, Y Lu, ZY Tian , QT Zheng, . CRYSTAL STRUCTURES OF OHMEFENTSNYL STEREOISOMERSJ. Acta Pharmaceutica Sinica, 1994, 29(6): 433-437.
Citation: ZX Wang, YC Zhu, RY Ji, Y Lu, ZY Tian , QT Zheng, . CRYSTAL STRUCTURES OF OHMEFENTSNYL STEREOISOMERSJ. Acta Pharmaceutica Sinica, 1994, 29(6): 433-437.

羟甲芬太尼立体异构体的晶体结构

CRYSTAL STRUCTURES OF OHMEFENTSNYL STEREOISOMERS

  • 摘要: 对强效镇痛剂羟甲芬太尼的两个光学异构体体cis-(3R,4S,2′R)-羟甲芬太尼(I)和trans-(3R,4R,2′S)-羟甲芬太尼(Ⅱ)进行了X-射线衍射晶体结构分析。两个异构体均有一个sp3N(l)原子和一个sp2N(7)原子。哌啶环呈椅式构象,顺式异构体I的3-甲基处于直立键,4-N-苯基丙酰胺基处于平伏键;反式异构体II的3-甲基与4-N-苯基丙酰胺基均处于平伏键。在I分子中,C(4)原子与4-丙酰胺基组成的平面与N-苯环平面近似相互垂直,而在II中,两平面的二面角近似为100℃。两异构体分子中均存在分子内氢键O(1)一H…N(1),反式异构体II还存在分子间氢键O(1)一H(A)…O(2)(B)。

     

    Abstract: Ohmefentanyl,N-1-(2-hydroxyl-2 phenyl)-3-methyl-piperidyl-N-phenylpropanamide,is a new and potent analgesic agent.Two stereoisomers :cis-(3R,4S,2′R)-ohmefentanyl(Ⅰ) and trans-( 3R,4R,2′S)-ohmefentanyl(Ⅱ),were selected for X-Ravcrystallographic study.The two isomers were shown tO have an sp3N(1)and an sp2N(7) and thepiperidine ring has a chair conformation,The cis-isomerⅠhas an axial 3-methyl with an equatorial 4-N-phenylpropanamide group, while the two groups of the trans-isomer Ⅱ are all equatorial. In Ⅰmolecule , the plane formed by the 4-propanamide group and atom C(4)is almost perpendicular to the4-N-phenyl ring plane; in Ⅱ, the dihedral angle of the two planes is about 100°. Intramolecularhydrogen bond of O(1)一H…N(1) occurs in both the two isomers and isomer Ⅱ is also involved inintermolecular hydrogen bond O(1)一H(A)…O(2)(B).

     

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