848142-49-4

Upstream product

• 43192-31-0 2-bromo-4-methoxybenzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 54788-18-0 2-bromo-1-(bromomethyl)-4-methoxybenzene 

Downstream Products

• 848142-83-6 7-bromo-6-methoxy-2-(4-methoxyphenyl)-2H-indazole 

Relevant academic research and scientific papers

Assembly of Fully Substituted 2H-Indazoles Catalyzed by Cu2O Rhombic Dodecahedra and Evaluation of Anticancer Activity

Simultaneous C?N, and N?N bond-forming methods for one-pot transformations are highly challenging in synthetic organic chemistry. In this study, the Cu2O rhombic dodecahedra-catalyzed synthesis of 2H-indazoles is demonstrated with good to excellent yields from readily available chemicals. This one-pot procedure involves Cu2O nanoparticle-catalyzed consecutive C?N, and N?N bond formation followed by cyclization to yield 2H-indazoles with broad substrate scope and high functional group tolerance. Various cell-based bioassay studies demonstrated that 2H-indazoles inhibit the growth of cancer cells, typically through induction of apoptosis in a dose-dependent manner. Moreover, 2H-indazoles tested in the MDA-MB-468 cell line were capable of inhibiting cancer cell migration and invasion. Thus, it is shown that 2H-indazoles have potent in vitro anticancer activity that warrant further investigation of this compound class.

Indazole estrogens: Highly selective ligands for the estrogen receptor β

The estrogen receptors, ERα and ERβ, are important pharmaceutical targets. To develop ERβ-selective ligands, we synthesized a series of nonsteroidal compounds having a phenyl-2H-indazole core with different groups at C-3. Several of these show high affinity and good ERβ selectivity, especially those with polar and/or polarizable substituents at this site (halogen, CF3, nitrile); the best compounds have affinities for ERβ comparable to estradiol, with ERβ affinity selectivity >100. This potency and ERβ selectivity is also seen in cell-based transcriptional assays, where several compounds showed ERβ efficacies equivalent to that of estradiol with ERβ potency selectivities of 100. These compounds might prove useful as selective pharmacological probes to study the biological actions of estrogens mediated through ERβ, and they might lead to the development of useful pharmaceuticals. These findings also contribute to an evolving pharmacophore that characterizes certain nonsteroidal ligands having high ERβ subtype affinity and potency selectivity.