α-Trichloromethylsulfonyl-5-nitro-2-furaldehydes, a new type of SH-group uncouplers and intermediates in the synthesis of 5-nitro-2-furylarylnitrilimines
1985 ◽
Vol 50
(2)
◽
pp. 357-364
◽
Trichloromethylsulfonyl-5-nitro-2-furaldehyde 4-X-phenylhydrazones I (X = H, CH3, Cl, CN, NO2, COOC2H5) were obtained by reacting 4-X-phenyldiazonium salts with 5-nitrofurfuryltrichloromethyl sulfone. These compounds react with diazomethane and trimethylamine to give the corresponding N-methylated derivatives and nitrilimines, respectively, the latter under elimination of trichlorosulfinic acid. The hydrazone-diaziridine tautomerism was studied by 1H, 15N, and 13C NMR methods; also the IR and UV spectra of the compounds synthesized are discussed. All hydrazones showed a very strong effect on the stimulation of mitochondria respiration and constitute a new type of SH-group uncouplers acting already in a 10-8 mol l-1 concentration.
1980 ◽
Vol 45
(8)
◽
pp. 2247-2253
◽
Keyword(s):
2000 ◽
Vol 6
(19)
◽
pp. 3645-3653
◽
1996 ◽
Vol 2
(5)
◽
pp. 529-538
◽
1979 ◽
Vol 44
(6)
◽
pp. 1761-1771
◽
Keyword(s):