51009-27-9Relevant academic research and scientific papers
N-Phenyl-1,2,3,4-tetrahydroisoquinoline: An Alternative Scaffold for the Design of 17β-Hydroxysteroid Dehydrogenase 1 Inhibitors
Mottinelli, Marco,Sinreih, Ma?a,Ri?ner, Tea L.,Leese, Mathew P.,Potter, Barry V. L.
, p. 259 - 291 (2020/12/07)
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.
Structural and Computational Analysis of Organic Fluorine-Mediated Interactions in Controlling the Crystal Packing of Tetrafluorinated Secondary Amides in the Presence of Weak C-H···O=C Hydrogen Bonds
Choudhury, Angshuman R.,Singla, Labhini,Yadav, Hare Ram
, (2022/02/07)
The structural and computational analysis of small organic compounds containing four fluorine atoms is the theme of this manuscript. A library of fluorinated compounds containing a secondary amide (-CONAr2) group has been synthesized and structurally char
Compounds and methods for modulation of estrogen receptors
-
, (2008/06/13)
Compounds that modulate the estrogen receptor (ER) are disclosed, as well as pharmaceutical compositions containing the same. In a specific embodiment, the compounds are selective for ER-β over ER-α. Methods are disclosed for modulating ER-β in cell and/o
Compounds and methods for modulation of estrogen receptors
-
, (2008/06/13)
Compounds that modulate the estrogen receptor (ER) are disclosed, as well as pharmaceutical compositions containing the same. In a specific embodiment, the compounds are selective modulators for ER-β over ER-α. Methods are disclosed for modulating ER-β in
Antiimplantation Agents: Part II - 1,2-Diaryl-1,2,3,4-tetrahydroisoquinolines
Nagarajan, K.,Talwalker, P. K.,Kulkarni, C. L.,Shah, R. K.,Shenoy, S. J.,Prabhu, S. S.
, p. 83 - 97 (2007/10/02)
1,2-Diaryl-3,4-dihydroisoquinolinium derivatives (5) have been synthesised from N-aryl-N-aroyl-β-phenethylamines (4) and found to exhibit no antiimplantation activity in the rat whereas many of the corresponding tetrahydroisoquinolines (6) are active.Structure-activity relationships have also been studied. 1-(p-Fluorophenyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline (6u) and its nor derivative (6v) are very potent, while the ortho (6g) and the meta (6n) fluoro analogues as well as the des-fluoro derivative (6d) are quite active.Extensive biological tests have been carried out on 6g.The enantiomers (+)-6p*HCl and (-)-6q*HCl of 6n have similar activity profiles as that of 6n showing no separation of antiimplantation and estrogenic properties.Diastereomeric 2-(2-methyl-2-phenethyl)-1-phenyl-1,2,3,4-tetrahydroisoquinolines (13a and 13b) show similar properties, while the tetracyclic derivative 19 is inactive. 2-Phenoxyethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline (26) shows moderate activity, but 1-(β-phenethyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 29 is inactive.
