Chemistry of indoles carrying a basic function, Part 3. Synthesis of spiro[cyclopropane-1,3'[3H]indol]-2'(1'H)-ones with antihypoxic effects.
Hydroxyindolones (1-6, 15-16) were transformed into isatinylidenes (7, 9-13, 17-19) by dehydration with 4-toluenesulfonic acid. The dimer-type compounds (14, 20) were also isolated in a few cases. The obtained isatinylidenes were transformed into 3-spiro-cyclopropane-oxindoles (21-32) with dimethyloxosulfonium methylide. Compound 22 shows protective effects against hypobaric hypoxia and triethyltin induced brain edema.
Moldvai
I
I
Central Research Institute for Chemistry, Hungarian Academy of Sciences, Budapest, Hungary.
Gács-Baitz
E
E
Balázs
M
M
Incze
M
M
Szántay
C
C
D000399:Air Pressure; D000818:Animals; D001929:Brain Edema / Q000139:chemically induced / Q000209:etiology / Q000517:prevention & control*; D000860:Hypoxia / Q000150:complications / Q000188:drug therapy*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D009682:Magnetic Resonance Spectroscopy; D051381:Rats; D011918:Rats, Inbred SHR; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D014267:Triethyltin Compounds
D007211:Indoles; D013141:Spiro Compounds; D014267:Triethyltin Compounds