|
【结 构 式】 
|
【药物名称】 【化学名称】2-(2-Hydroxyethylsulfanyl)-3-methyl-1,4-naphthoquinone 【CA登记号】59147-84-1 【 分 子 式 】C13H12O3S 【 分 子 量 】248.30279 |
【开发单位】University of Pittsburgh (Originator) 【药理作用】Oncolytic Drugs, Cell Division Cycle CDC25 Phosphatase Inhibitors, Inhibitors of Signal Transduction Pathways |
合成路线1
Halogenation of vitamin K3 (menadione) (I) by means of bromine and NaOAc in AcOH furnished 3-bromo menadione (II). Subsequent displacement of the halogen of (II) by 2-mercaptoethanol (III) in the presence of imidazole yielded the desired (2-hydroxyethyl) thioether.
| 【1】 Kerns, J.K.; Carr, B.I.; Wilcox, C.S. (University of Pittsburgh); Antiproliferative naphthoquinones, derivs., compsns., and uses thereof. WO 0008495 . |
合成路线2
In an alternative procedure, the title compound was obtained by addition of 2-mercaptoethanol (III) to vitamin K3 oxide (menadione oxide) (IV) in the presence of imidazole.
| 【1】 Horikawa, A.; et al.; Synthesis of protein tyrosine phosphatase inhibitor and application for malignant pediatric tumor. 21st Symp Med Chem (Nov 28 2001, Kyoto) 2001, Abst 2P-05. |
| 【2】 Kerns, J.; Carr, B.; Dowd, P.; Finn, F.M.; Naganathan, s.; Thioalkyl derivatives of vitamin K3 and vitamin K3 oxide inhibit growth of Hep3B and HepG2 cells. Bioorganic Chemistry 1995, 23, 2, 101. |
Extended Information