Synthesis, Structures, and Properties of Helically Fused Anthraquinones with Unusually Close Carbonyl-Carbonyl Contacts.

Electron-deficient aromatic ketones consisting of three fused anthraquinone units were synthesized by oxidation of the corresponding fused anthracenes. X-ray analysis revealed that these compounds had nonplanar helical structures with unusual contacts, C=O⋅⋅⋅C=O 2.467 Å, between the inner carbonyl groups. The role of n⋅⋅⋅π* interactions in the short contacts was evaluated using a noncovalent interaction plot and natural bond orbital analysis. The dynamic process involving helical inversion was observed by the variable temperature 1 H NMR measurement of a derivative with 2,4,6-trimethylphenyl groups, and the barrier was estimated to be 77 kJ mol-1 . DFT calculations indicated that the helical inversion proceeded via a multistep mechanism. The characteristic spectroscopic and electrochemical data due to the electron-deficient anthraquinone units and the sterically congested carbonyl groups are discussed with the aid of DFT calculations.

MRI, CT and FDG-PET/CT findings of Wolffian tumor: four-case series.

ABSTARCT: PURPOSE: The purpose of this study is to describe the characteristic MRI, CT, and 18F-fluorodeoxyglucose-positron emission tomography/computed tomography (FDG-PET/CT) findings of Wolffian tumor. METHODS: We reviewed preoperative images in four surgical cases of Wolffian tumor. MRI was available for review in all cases with additional diffusion-weighted images (DWI) in three, and contrast-enhanced images in two. CT was available in three. FDG-PET/CT was obtained in two. RESULTS: Two patients were asymptomatic, while the other two presented with acute abdomen. On MRI, all tumors were well-defined masses of increased signals on T2WI. Three tumors were solid, whereas the other was solid and cystic. The normal ipsilateral ovary was identified in two patients of reproductive ages, but not in two postmenopausal patients. Tumors in two patients presented with acute abdomen were complicated by hemorrhage. All three tumors evaluated on DWI showed high intensities. Contrast-enhanced images of MRI and CT showed homogeneous enhancement as the same degree as the myometrium. On CT, one tumor contained punctate calcifications. FDG-PET/CT showed moderate FDG accumulation. CONCLUSION: Wolffian tumors may be typically solid extraovarian tumors occasionally associated with cysts and calcifications. Although they are benign, they mimic malignancy due to high intensities on DWI and increased FDG accumulation.