66996-59-6Relevant articles and documents
Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system
Satkar, Yuvraj,Ramadoss, Velayudham,Nahide, Pradip D.,García-Medina, Ernesto,Juárez-Ornelas, Kevin A.,Alonso-Castro, Angel J.,Chávez-Rivera, Ruben,Jiménez-Halla, J. Oscar C.,Solorio-Alvarado, César R.
, p. 17806 - 17812 (2018/05/28)
A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3. Our DFT calculations suggest that this is likely the brominating active species, which is prepared in situ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.
Catalytic electrophilic halogenations and haloalkoxylations by non-heme iron halides
Rana, Sujoy,Bag, Sukdev,Patra, Tuhin,Maiti, Debabrata
supporting information, p. 2453 - 2458 (2014/09/30)
Synthetic non-heme iron halides promote sub-stoichiometric aliphatic halogenation reactions via a radical mechanism. Complementary to such activity, we have developed an electrophilic halogenation of arenes employing non-heme iron halides. A catalytic version of these reactions has also been developed using potassium halide as the source of halogen atom for arenes at room temperature. Efforts towards understanding the mechanism of these catalytic halogenation reactions led to the discovery of the haloalkoxylation of olefins by a non-heme iron complex. Implications of these findings with respect to natural transformations are also discussed.
New drug-like hydroxyphenylnaphthol steroidomimetics as potent and selective 17β-hydroxysteroid dehydrogenase type 1 inhibitors for the treatment of estrogen-dependent diseases
Marchais-Oberwinkler, Sandrine,Wetzel, Marie,Ziegler, Erika,Kruchten, Patricia,Werth, Ruth,Henn, Claudia,Hartmann, Rolf W.,Frotscher, Martin
scheme or table, p. 534 - 547 (2011/03/21)
Inhibition of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) is a novel and attractive approach to reduce the local levels of the active estrogen 17β-estradiol in patients with estrogen-dependent diseases like breast cancer or endometriosis. With the aim of optimizing the biological profile of 17β-HSD1 inhibitors from the hydroxyphenylnaphthol class, structural optimizations were performed at the 1-position of the naphthalene by introduction of different heteroaromatic rings as well as substituted phenyl groups. In the latter class of compounds, which were synthesized applying Suzuki-cross coupling, the 3-methanesulfonamide 15 turned out to be a highly potent 17β-HSD1 inhibitor (IC50 = 15 nM in a cell-free assay). It was also very active in the cellular assay (T47D cells, IC50 = 71 nM) and selective toward 17β-HSD2 and the estrogen receptors α and β. It showed a good membrane permeation and metabolic stability and was orally available in the rat.
