Category: 799274-06-9

Recommanded Product: 799274-06-9On September 13, 2012 ,《3-(3,4-Dihydroisoquinolin-2(1H)-ylsulfonyl)benzoic Acids: Highly Potent and Selective Inhibitors of the Type 5 17-β-Hydroxysteroid Dehydrogenase AKR1C3》 was published in Journal of Medicinal Chemistry. The article was written by Jamieson, Stephen M. F.; Brooke, Darby G.; Heinrich, Daniel; Atwell, Graham J.; Silva, Shevan; Hamilton, Emma J.; Turnbull, Andrew P.; Rigoreau, Laurent J. M.; Trivier, Elisabeth; Soudy, Christelle; Samlal, Sharon S.; Owen, Paul J.; Schroeder, Ewald; Raynham, Tony; Flanagan, Jack U.; Denny, William A.. The article contains the following contents:

A high-throughput screen identified 3-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)benzoic acid as a novel, highly potent (low nM), and isoform-selective (1500-fold) inhibitor of aldo-keto reductase AKR1C3: a target of interest in both breast and prostate cancer. Crystal structure studies showed that the carboxylate group occupies the oxyanion hole in the enzyme, while the sulfonamide provides the correct twist to allow the dihydroisoquinoline to bind in an adjacent hydrophobic pocket. SAR studies around this lead showed that the positioning of the carboxylate was critical, although it could be substituted by acid isosteres and amides. Small substituents on the dihydroisoquinoline gave improvements in potency. A set of “”reverse sulfonamides””, e.g., I (R = CO2H, R1 = H; R = H, R1 = CO2H), showed a 12-fold preference for the R stereoisomer. The compounds showed good cellular potency, as measured by inhibition of AKR1C3 metabolism of a known dinitrobenzamide substrate, with a broad rank order between enzymic and cellular activity; but amide analogs were more effective than predicted by the cellular assay. In addition to this study using 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride, there are many other studies that have used 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9Recommanded Product: 799274-06-9) was used in this study.

7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Recommanded Product: 799274-06-9 It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Shonberg, Jeremy; Draper-Joyce, Christopher; Mistry, Shailesh N.; Christopoulos, Arthur; Scammells, Peter J.; Lane, J. Robert; Capuano, Ben published an article in Journal of Medicinal Chemistry. The title of the article was 《Structure-activity study of N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652), a bitopic ligand that acts as a negative allosteric modulator of the dopamine D2 receptor》.Name: 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride The author mentioned the following in the article:

The authors recently demonstrated that SB269652 I engages one protomer of a dopamine D2 receptor (D2R) dimer in a bitopic mode to allosterically inhibit the binding of dopamine at the other protomer. Herein, the authors investigate structural determinants for allostery, focusing on modifications to three moieties within I. The authors find that orthosteric “”head”” groups with small 7-substituents were important to maintain the limited neg. cooperativity of analogs of I, and replacement of the tetrahydroisoquinoline head group with other D2R “”privileged structures”” generated orthosteric antagonists. Addnl., replacement of the cyclohexylene linker with polymethylene chains conferred linker length dependency in allosteric pharmacol. The authors validated the importance of the indolic NH as a hydrogen bond donor moiety for maintaining allostery. Replacement of the indole ring with azaindole conferred a 30-fold increase in affinity while maintaining neg. cooperativity. Combined, these results provide novel SAR insight for bitopic ligands that act as neg. allosteric modulators of the D2R. In the experiment, the researchers used 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9Name: 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride)

7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Name: 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

《[2+3] Annulative Coupling of Tetrahydroisoquinolines with Aryliodonio diazo compounds To Access 1,2,4-Triazolo[3,4-a]isoquinolines》 was written by Ansari, Monish Arbaz; Khan, Shahnawaz; Ray, Subhasish; Shukla, Gaurav; Singh, Maya Shankar. Application In Synthesis of 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride And the article was included in Organic Letters on August 19 ,2022. The article conveys some information:

Base promoted one-pot annulative coupling of 1,2,3,4-tetrahydroisoquinolines (THIQs) with hypervalent iodine(III) species aryliodonio diazo compounds I (R = COOEt, COOtBu, COOBn, menthyl) has been devised for the direct construction of 1,2,4-triazolo[3,4-a]isoquinoline derivatives II (R = COOEt, COOtBu, COOBn, menthyl; R1 = H, 7-Me, 9-F, etc.) at room temperature in open air for the first time. This approach involves [2+3] cascade annulation of nucleophilic THIQ with an electrophilic aryliodonio diazo compound via N-H and α-C1(sp3)-H difunctionalization of THIQ. In the experiment, the researchers used many compounds, for example, 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9Application In Synthesis of 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride)

7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride(cas: 799274-06-9) belongs to tetrahydroisoquinoline. Tetrahydroisoquinoline Reactions: As a secondary amine, tetrahydroisoquinoline has weakly basic properties and forms salts with strong acids.Application In Synthesis of 7-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride It can be dehydrogenated to give isoquinoline and hydrogenated to decahydroisoquinoline. Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.

Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem