Syntheses of Novel Selenium-Containing Compounds and Their Application to the Pharmaceutical Science

Research Project

Project/Area Number	61571011
Research Category	Grant-in-Aid for General Scientific Research (C)
Allocation Type	Single-year Grants
Research Field	Chemical pharmacy
Research Institution	Gifu Pharmaceutical University
Principal Investigator	HORI Mikio Gifu Pharmaceutical University, 薬学部, 教授 (80082957)
Co-Investigator(Kenkyū-buntansha)	IWAMURA Tatsunori Gifu Pharmaceutical University, 薬学部, 助手 (70184900) SHIMIZU Hiroshi Gifu Pharmaceutical University, 薬学部, 講師 (00082983) KATAOKA Tadashi Gifu Pharmaceutical University, 薬学部, 助教授 (00082975)
Project Period (FY)	1986 – 1988
Project Status	Completed (Fiscal Year 1988)
Budget Amount *help	¥2,300,000 (Direct Cost: ¥2,300,000) Fiscal Year 1988: ¥100,000 (Direct Cost: ¥100,000) Fiscal Year 1987: ¥600,000 (Direct Cost: ¥600,000) Fiscal Year 1986: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywords	Selenurane / Selenonium Ylide / Selenonium Salts / Thermal Reaction / Electrophilic Reaction / Stereoisomer / Rearrangement / 免疫賦活作用 / 抗癌活性 / セレノキサンテン / セレノキサンテニウム塩 / セレノアントラセン / ジベンゾジヒドロセレネピン / セレノクロマン / セレンイソド / セリノニウム塩
Research Abstract	1. Syntheses and Reactions of Cyclic selenuranes 10-Chloro-10, 9-epoxy- or 10, 9-epoxyalkano-selenoxanthenes were prepared by treatment of 9-hydroxy- or 9-hydroxyalkyl-selenoxanthenes with N-chlorosuccinimide. Structures of these selenuranes were determined by comparison of their NMR spectra with those of the corresponding selenonium salts. Their reactions such as hydrolysis, reduction and thermal reactions were investigated. 2. Syntheses and Reactions of Cyclic Selenonium exo-Ylides Isoselenochromanium ylides stabilized by the electron-withdrawing groups were synthesized from the dichloroselenurane or the selenilimine. Other selenonium ylides were generated by deprotonation of the selenonium salts. The stable ylides reacted with dimethyl acetylenedicarboxylate to give the furan derivatives or the benzoselenonin derivatives. 3. Syntheses and Reactions of Selenoxanthenium salts various kinds of selenoxanthenium salts were synthesized and their stereostructures were determined by analyses of their NMR spectra. The unstable selenoxanthenium ylides generated from the selenoxanthenium salts underwentthe 1, 4-rearrangement or the dealkylation (dearylation) depending upon the configuration of 9- and 10-substituents. 4. Synthesis of Biologically Active Selenonium Salts Dimethyl tetrahydrofuranylethyl selenonium salt was synthesized and tested for the immunological anticancer activity.