Olivier A, Creuven I, Evrard C, Evrard G, Dory M, van Aerschot A, Wigerinck P, Herdewijn P, Durant F
Laboratoire de Chimie Moléculaire Structurale, Facultés Universitaires N.-D. de la Paix, Namur, Belgium.
Antiviral Res. 1994 Aug;24(4):289-304. doi: 10.1016/0166-3542(94)90076-0.
Structural and electronic characteristics of 5-(5-chlorothien-2-yl)-2'-deoxyuridine (I), 5-(furan-2-yl)-2'-deoxyuridine (II), 5-(5-bromofuran-2-yl)-2'-deoxyuridine (III), 5-(3-bromoisoxazol-5-yl)-2'-deoxyuridine (V) and 5-(isoxazol-5-yl)-2'-deoxyuridine (IV) have been determined and compared to the BVDU (VI) characteristics in order to explain their respective affinity for the herpes simplex virus type 1 thymidine kinase (TK). Molecular structure of 5-(5-chlorothien-2-yl)-2'-deoxyuridine has been obtained using single crystal X-ray crystallography. Electrostatic potential maps, energy and topology of frontier orbitals were computed at the ab initio MO STO-3G and STO-3G level. These studies reveal that the electrostatic potential energy maps are clearly dependent on the affinity of the compound for the enzyme.
已测定5-(5-氯噻吩-2-基)-2'-脱氧尿苷（I）、5-(呋喃-2-基)-2'-脱氧尿苷（II）、5-(5-溴呋喃-2-基)-2'-脱氧尿苷（III）、5-(3-溴异恶唑-5-基)-2'-脱氧尿苷（V）和5-(异恶唑-5-基)-2'-脱氧尿苷（IV）的结构和电子特性，并与BVDU（VI）的特性进行比较，以解释它们对单纯疱疹病毒1型胸苷激酶（TK）的各自亲和力。5-(5-氯噻吩-2-基)-2'-脱氧尿苷的分子结构已通过单晶X射线晶体学获得。在从头算MO STO-3G和STO-3G水平上计算了静电势图、前沿轨道的能量和拓扑结构。这些研究表明，静电势能图明显取决于化合物对该酶的亲和力。
