CAS: 135729-73-6; (R)-2-((S)-Quinuclidin-3-yl)-2,3,3A,4,5,6-Hexahydro-1H-Benzo[de]Isoquinolin-1-One

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(S)-2-(1-azabicyclo[2.2.2]°Ct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid 5,6,7,8-tetrahydronaphthylene-1-carboxylic acid chloride °Ct-3-yl>-5,6,7,8-tetrahydronaphthalene-1-carboxamideN-(S)-1-azabicyclo2.2.2°Ct-3-yl-5,6,7,8-tetrahydronaphthalene-1-carboxamide palonosetron hydr°Chloride palonosetron hydr°Chloride Palonosetron N-oxide

📜(S)-N-(1-氮杂双环环[2.2.2]-3-辛基)-5,6,7,8-四氢-1-萘羧酰胺置于palladium On Activated Charcoal 盐酸,正丁基锂,氢气体系中,用 四氢呋喃,正己烷 用作溶剂,化学反应 361.0H,反应生成帕洛诺司琼非对映异构体(R.S)
参考文献:2-(Quinuclidin-3-yl)Pyrido[4,3-B]Indol-1-Ones And Isoquinolin-1-Ones. Potent Conformationally Restricted 5-Ht3 Receptor Antagonists
标题:2-(Quinuclidin-3-yl)Pyrido[4,3-B]Indol-1-Ones And Isoquinolin-1-Ones. Potent Conformationally Restricted 5-Ht3 Receptor Antagonists
摘要:Several Series Of N-(Quinuclidin-3-yl)Aryl And Heteroaryl-Fused Pyridones Were Synthesized And Evaluated For 5-Ht3 Receptor Affinity. In The Heteroaryl Series,2-(Quinuclidin-3-yl)Tetrahydropyrido-[4,3-B]Indol-1-One (8A) And The 4,5-Alkano-Bridged Analogues (14 And 15) Displayed High 5-Ht3 Receptor Affinity With Pk(I) Values > 9. The (3S)-Quinuclidinyl Isomers Had > 10 Fold Higher Affinity Than The (3R)-Isomers. In A Series Of 2-Quinuclidin-3-yl)Isoquinolin-1-Ones,Derivatives Substituted With Small Lipophilic Groups (25B-E) And With 4,5-Alkano-Bridges (34-36) Also Displayed High Affinity. In Particular,The Hexahydro-1H-Benz[de]Isoquinolinone (S,S)-37 Was The Highest Affinity 5-Ht3 Receptor Ligand Prepared (Pk(I) 10.4). A Number Of The High Affinity Ligands Were Shown To Be Potent 5-Ht3 Receptor Antagonists In Vivo As Determined By Inhibition Of The B-J Reflex In The Anesthetized Rat. Again,(S,S)-37 Was The Most Active Agent Tested (Id50 0.02 Mug/kg Iv),And This Compound Was Also Potent In Blocking Cisplatin-Induced Emesis In Both The Ferret And The Dog. Computer Modeling Studies Were Performed,And Previously Reported 5-Ht3 Receptor Antagonist Pharmacophore Models Were Refined To Include A Key Lipophilic Binding Domain.
Doi:10.1021/jm00070A008