SLNU, SLCNU

Chemical Name: 1-(2-Chloroethyl)-1-nitroso-3-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)urea
项目整合开发状态: Preclinical
项目研究机构: Natl. Fdn. Cancer Research (Originator), University of Wisconsin-Milwaukee (Originator)
合成路线:The condensation of 1-oxyl-2,2,6,6-tetramethyl-4-aminopiperidine (I) with 2-chloroethyl isocyanate (II) gives 1-(2-chloroethyl)-3-(1-oxyl-2,2,6,6-tetramethylpiperidinyl)urea (III).The nitrosation of (III) with dinitrogen tetraoxide in methylene chloride yields SLCNU.

合成路线:The nitrosation of (IV) with dinitrogen tetraoxide in methylene chloride affords (V),which is condensed with (I) to yield SLCNU.

合成路线:Lithiation of 6-methoxybenzothiophene (I),followed by condensation with cyclohexanone (II) provides the hydroxycyclohexyl benzothiophene (III),which is further dehydrated to the cyclohexenyl analogue (IV) under acidic conditions (1).In a related procedure,the cyclohexenyl benzothiophene (IV) is prepared by condensation of the lithiated derivative of (I) with cyclohexenyl triflate (V) in the presence of ZnCl2 and Pd(PPh3)4 (2).Catalytic hydrogenation of olefin (IV) over Pd/C leads to the cyclohexyl benzothiophene (VI) (1,2).Subsequent Friedel-Crafts acylation of (VI) with 4-(2-chloroethoxy)benzoyl chloride (VII) yields ketone (VIII) (1).Displacement of the chloride group in (VIII) with piperidine furnishes the piperidinyl ethoxy derivative (IX).The methyl ether (IX) is finally cleaved by treatment with AlCl3 and EtSH to produce the target phenol derivative (1,3-5).