Preparation of some sulfonamide and diaminodiphenyl sulfone analogs of 1,4-naphthoquinone

Abstract

After boiling off the acetone, 500 ml of ice water was added and the solution was saturated with NaCl. The reaction mixture was extracted (EUO) and the extract was dried (Na2C03).Stripping off the ether left a brown viscous residue. Trituration of the residue with MeOH yielded 4.2 g (31%) of IV, mp 121.5-122.5°(MeOH).The N-phenylpiperazines listed in Table I were synthesized by analogous procedures.l-(2-Bromo-4,5-dimethoxyphenyl)-4-(2-methyl-4,5-dimethoxypheny 1 )piperazine.-A solution of 31 g (0.05 mole) of II ditosylate and 25 g (0.15 mole) 4-methyl-5-aminoveratrole in 1 1. of 50% Me2C0~H20 -was refluxed for 2 days. A solid which precipitated during the course of the reaction was filtered. After washing (Et20) and recrystallization (¿-PrOH), it gave 4.2 g of white glistening flakes.l-(2-Bromo-4,5-dimethoxyphenyl)-4-tetramethyIenepiperazinium Chloride.-A solution of III (14 g) and 20 ml of pyrrolidine in 150 ml of THE was refluxed for 2 days. Filtration of the cooled reaction mixture gave 16 g of a tan solid. Extraction with hot z-PrOH left the piperazinium salt as a white solid (8.9 g).The piperazinium salts listed in Table II were prepared in a like manner.

Synthesis and Anticancer Evaluation of 1,4‐Naphthoquinone Derivatives Containing a Phenylaminosulfanyl Moiety

“…Commercially available 2,3‐dichloro‐1,4‐naphthoquinone 1 was used as a starting material and was reacted with 4‐aminophenyl sulfone 2 in water to produce 6‐(4‐(4‐aminophenylsulfonyl)phenylamino)‐3‐chloronaphthalene‐1,4‐dione 3 . Compound 3 was prepared previously by Carroll et al . using a rather involved method.…”

“…Compound 3 was prepared previously by Carrolle tal. [20] using ar ather involved method. Am ixture of 2,3-dichloro-1,4-naphthoquinone and 4-aminophenyl sulfonamide hydrochloride salt in ethanol, in the presence of N,N-diethylaniline as ac atalyst, was held at reflux for 18 h; the product yield was approximately 72 %.…”