347976-83-4

Upstream product

• 85274-96-0 2-(3-Methoxy-phenyl)-N-phenyl-acetamide 
• 51009-27-9 [2-(3-Methoxy-phenyl)-ethyl]-phenyl-amine 
• 103-80-0 phenylacetyl chloride 
• 6834-42-0 3-methoxyphenylacetic acid chloride 
• 1798-09-0 m-methoxyphenylacetic acid 
• 103-82-2 phenylacetic acid 

Downstream Products

• 347981-09-3 1-benzyl-6-methoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

N-Phenyl-1,2,3,4-tetrahydroisoquinoline: An Alternative Scaffold for the Design of 17β-Hydroxysteroid Dehydrogenase 1 Inhibitors

17β-Hydroxysteroid dehydrogenases catalyse interconversion at the C17 position between oxidized and reduced forms of steroidal nuclear receptor ligands. The type 1 enzyme, expressed in malignant cells, catalyses reduction of the less-active estrone to estradiol, and inhibitors have therapeutic potential in estrogen-dependent diseases such as breast and ovarian cancers and in endometriosis. Synthetic decoration of the nonsteroidal N-phenyl-1,2,3,4-tetrahydroisoquinoline (THIQ) template was pursued by using Pomeranz-Fritsch-Bobbitt, Pictet-Spengler and Bischler-Napieralski approaches to explore the viability of this scaffold as a steroid mimic. Derivatives were evaluated biologically in vitro as type 1 enzyme inhibitors in a bacterial cell homogenate as source of recombinant protein. Structure-activity relationships are discussed. THIQs possessing a 6-hydroxy group, lipophilic substitutions at the 1- or 4-positions in combination with N-4′-chlorophenyl substitution were most favourable for activity. Of these, one compound had an IC50 of ca. 350 nM as a racemate, testifying to the applicability of this novel approach.

Tetrahydroisoquinolines as subtype selective estrogen agonists/antagonists

Two series of 6-hydroxy and 7-hydroxy tetrahydroisoquinolines were prepared. Evaluating a range of C-1, C-4, and N-substituents led to the discovery of ER α and ER β selective analogs.