ERβ ligands. Part 4: Synthesis and structure–activity relationships of a series of 2-phenylquinoline derivatives

Convergent Synthesis of 2-Aryl-Substituted Quinolines by Gold-Catalyzed Cascade Reaction

“…[5][6][7] Therefore, quinoline compounds have inspired the development of new synthetic methods 8,9) for the formation of the N-heterocyclic scaffold due to their potential utility in the pharmaceutical industry. As classical and conventional synthetic methods, the Skraup,10) Doebner and von Miller, 11) Combes, 12) Friedländer, 13) and Pfitzinger 14) quinoline syntheses are well known; however, these methods often encounter problems with functional group compatibility as they require strong acidic or basic conditions.…”

Creation of Novel Biofunctional Molecules for Target-Selective Photodegradation of Proteins and Carbohydrates: A Synthetic and Chemical Biological Study for the Post-Genome Era

“…The 2 phenylquinoline scaffold is similar to estrogen in terms of its af nity for ER α. 9 Modulation of ER α function is an important factor in a variety of diseases, including breast cancer and osteoporosis. 10 To determine whether 2 phenylquino- line is capable of modulating ER α function, we examined its photoinduced protein degrading activity against ER α using a long wavelength UV irradiation (365 nm) without any additives.…”

A Green, Solvent-Free One-Pot Synthesis of Disubstituted Quinolines via A3-Coupling Using 1 Mol% FeCl3

“…12), which is commonly known to be fundamental in its binding to the ER. [24] The 2-phenylquinoline derivatives ( Fig. 13a and b)showed high affinity towards the ERβ binding site with IC50 values between 3 -5 nM.…”

“…13a and b)showed high affinity towards the ERβ binding site with IC50 values between 3 -5 nM. [24] Figure 12: Structure of Genistein which is commonly used for binding to ERβ. It can be seen from the above examples that the quinoline moiety forms the backbone of many complex compounds that display biological activity.…”

“…[23] The ligand binding domains (LBD) of ERα and ERβ have a modest variation in the binding cavities thus presenting a great challenge in the development of ER ligands. [24] Vu et al synthesized 2-phenylquinoline compounds that closely resemble genistein (Fig. 12), which is commonly known to be fundamental in its binding to the ER.…”