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Etiological workup included the following: negative viral serology (hepatitis A virus immunoglobulin M, hepatitis B virus surface antigen and core antibody, hepatitis C virus antibody [polymerase chain reaction assay], cytomegalovirus DNA and Epstein-Barr virus immunoglobulin M); negative syphilis rapid plasma regain; negative autoimmune markers (antinuclear antibody, antiliver kidney muscle antibody, antimitochondrial antibody and antismooth muscle antibody); and normal serum gamma globulins. Extensive toxicology screening was negative, with no features of acetaminophen toxicity (acidosis, high lactate or renal failure). She had normal levels of ferritin, ceruloplasmin and alpha-1 antitrypsin. A pregnancy test was negative. A computed tomography scan of her abdomen revealed a normal size liver with a patent portal vein, hepatic artery, hepatic vein and normal biliary anatomy. Her spleen was normal and no ascites was noted.

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Computerized molecular modeling studies on the interactions of the antiestrogen tamoxifen (1) and its analogues bound to the calcium-binding protein calmodulin have guided the rational design of more potent antagonists. Compounds with either three or four methylene units in the basic side chain or slim lipophilic 4-substituents were expected to be more potent. All compounds were tested for antagonism of the calmodulin-dependent activity of cAMP phosphodiesterase and for binding affinity to the estrogen receptor from rat uteri. Some compounds were assayed for cytotoxicity against MCF-7 breast tumor cells in vitro. Introduction of lipophilic 4-substituents was accomplished by using palladium(0)-catalyzed coupling reactions with a 4-iodinated precursor. Both the 4-ethynyl (16 and 17) and 4-butyl (18 and 19) compounds were more potent calmodulin antagonists than tamoxifen. Extension of the basic aminoethoxy side chain of 4-iodotamoxifen (3) and idoxifene (2) ((E)-1-[4-[2-(N-pyrrolidino)ethoxy]phenyl]-1-(4-iodophenyl)-2-phen yl-1- butene) by one or two methylene units resulted in modest gains in calmodulin antagonism (10-13). All the compounds assayed retained estrogen receptor binding characteristics. The compound possessing the optimal combination of calmodulin antagonism and estrogen receptor binding was 12 ((E)-1-[4-[3-(N-pyrrolidino)propoxy]phenyl]-1-(4-iodophenyl)-2-phe nyl-1 - butene) (IC50 = 1.1 microM, RBA = 23). Correlation between calmodulin antagonism and cytotoxicity was demonstrated for selected compounds. 781b155fdc