0000000000415289
AUTHOR
Jukka Gynther
SULFUR ANALOGUES OF POLYCHLORINATED DIBENZO-p-DIOXINS, DIBENZOFURANS AND DIPHENYL ETHERS AS INDUCERS OF CYP1A1 IN MOUSE HEPATOMA CELL CULTURE AND STRUCTURE-ACTIVITY RELATIONSHIPS
Three sulfur-containing compounds, 2,3,7,8-tetrachlorothianthrene (TCTA), 2,3,7,8-tetrachlorodibenzothiophene (TCDT), and 3,3[prime],4,4[prime]-tetrachlorodiphenyl sulfide (TCDPS), were analyzed for their CYP1A1-inducing potencies--measured as aryl hydrocarbon hydroxylase (AHH) and 7-ethoxyresorufin O-deethylase (EROD) activities--in mouse hepatoma cell culture Hepa-1. Marked differences in the induction potencies were observed among the three compounds studied and between 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and its sulfur analogue. The estimated EC50 values for TCDD, TCTA, and TCDT were about 8 pM, 700 pM, and 7.5 nM, respectively. TCDPS did not elicit any AHH/EROD induction. Compar…
2(S)-Amino-3-[1H-imidazol-4(5)-yl]propyl cyclohexylmethyl ether dihydrochloride and 2(S)-amino-3-[1H-imidazol-4(5)-yl]propyl 4-bromobenzyl ether dihydrochloride
(Cyclohexylmethyloxymethyl)(1H-imidazol-4-iomethyl)-(S)-ammonium dichloride, C(13)H(25)N(3)O(+).2Cl(-), and (4-bromobenzyl)(1H-imidazol-4-iomethyl)-(S)-ammonium dichloride, C(13)H(18)BrN(3)O(+).2Cl(-), are model compounds with different biological activities for evaluation of the histamine H3-receptor activation mechanism. Both title compounds occur in almost similar extended conformations.
Structural studies of acyl esters of entacapone
Abstract The crystal structures of entacapone [(E)-2-cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide] and three of its acyl esters were solved. Entacapone, and its monopivaloate and diacetate derivatives, exist in the E-form while its dibenzoate derivative adopts the Z-form in the crystalline state. The ethyl substituents of the E-form are not freely rotating, as demonstrated by the broad signals in the 1H and 13C NMR spectra. The rotation barrier for the E-form was defined by the crystal structures, which show that free rotation of the ethyl substituents is blocked by the cyano-group.