Potential Anticancer Agents.¹ XXXVI. Alkylating Agents Derived from 5-Aminouracil

An Efficient Synthesis and In vitro Cytostatic Activity of 5-Aminosulfonyl Uracil Derivatives

“…benzenesulfonamide (2) Compound 2 was made in a different way than described in Ref. [48]. According to the general procedure, 5-aminouracil 1 (0.5 g, 3.93 mmol) and tosyl chloride (0.749 g, 3.93 mmol) in pyridine (29 mL) were reacted for 19 h. Recrystallization from aqueous methanol gave the analytically pure product 2 as white crystals: 1.08 g (98 %; lit.…”

“…According to the general procedure, 5-aminouracil 1 (0.5 g, 3.93 mmol) and tosyl chloride (0.749 g, 3.93 mmol) in pyridine (29 mL) were reacted for 19 h. Recrystallization from aqueous methanol gave the analytically pure product 2 as white crystals: 1.08 g (98 %; lit. [48] 49 %); Rf = 0.55 (CH2Cl2/MeOH 9:1); m.p. >300 °C; UV (MeOH): λmax/nm: 218 and 272; log ε/ dm 3 mol -1 cm -1 : 4.…”

“…When potassium salt of 5-aminouracil is allowed to react with methyl iodide alkylation takes place in the N1 and N3 positions of the pyrimidine ring with formation of 1,3-dimethyl-5-aminouracil. [48] Treatment of 5-aminouracil 1 with p-toluenesulfonyl chloride in aq. sodium hydroxide gave 5-aminotosyl uracil 2 in 49 % yield, [48] while 5-sulfanilamidouracil [49] was synthesized by reacting 5-aminouracil 1 and N-acetylsulfanilyl chloride in pyridine, followed by deprotection of N-acetyl group in aqueous sodium hydroxide (52 % yield).…”

“…[48] Treatment of 5-aminouracil 1 with p-toluenesulfonyl chloride in aq. sodium hydroxide gave 5-aminotosyl uracil 2 in 49 % yield, [48] while 5-sulfanilamidouracil [49] was synthesized by reacting 5-aminouracil 1 and N-acetylsulfanilyl chloride in pyridine, followed by deprotection of N-acetyl group in aqueous sodium hydroxide (52 % yield). Pecorari et al [50] showed that in the reaction of 4-acetamido and 4-nitrobenzenesulfonyl chloride with 5-aminouracil 1 in aq.…”

Synthesis and Bioevaluation of a Series of Fatty Acid Esters of p- [N,N- Bis(2-chloroethyl)amino]phenol

“…The final nitrogen mustard products (IVa-I) were prepared by the method of Benitez et al (13). Although the procedure was conducted a t low temperature, tarry crude products were always obtained initially and final yields were relatively low (2242%).…”