20944-13-2Relevant academic research and scientific papers
Biomimetic Total Synthesis of Dysoxylum Alkaloids
Puerto Galvis, Carlos E.,Kouznetsov, Vladimir V.
, p. 15294 - 15308 (2019/11/29)
A five-step total synthesis of Dysoxylum alkaloids has been achieved using a biomimetic approach from zanthoxylamide protoalkaloids. The synthesis featured a direct amidation and a Bischler-Napieralski reaction to form the dihydroisoquinoline ring, which
Effect of 1-Substitution on Tetrahydroisoquinolines as Selective Antagonists for the Orexin-1 Receptor
Perrey, David A.,German, Nadezhda A.,Decker, Ann M.,Thorn, David,Li, Jun-Xu,Gilmour, Brian P.,Thomas, Brian F.,Harris, Danni L.,Runyon, Scott P.,Zhang, Yanan
, p. 599 - 614 (2015/04/27)
Selective blockade of the orexin-1 receptor (OX1) has been suggested as a potential approach to drug addiction therapy because of its role in modulating the brain's reward system. We have recently reported a series of tetrahydroisoquinoline-based OX1 selective antagonists. Aimed at elucidating structure-activity relationship requirements in other regions of the molecule and further enhancing OX1 potency and selectivity, we have designed and synthesized a series of analogues bearing a variety of substituents at the 1-position of the tetrahydroisoquinoline. The results show that an optimally substituted benzyl group is required for activity at the OX1 receptor. Several compounds with improved potency and/or selectivity have been identified. When combined with structural modifications that were previously found to improve selectivity, we have identified compound 73 (RTIOX-251) with an apparent dissociation constant (Ke) of 16.1 nM at the OX1 receptor and >620-fold selectivity over the OX2 receptor. In vivo, compound 73 was shown to block the development of locomotor sensitization to cocaine in rats. (Chemical Equation Presented).
Synthesis and radioligand binding studies of methoxylated 1,2,3,4-tetrahydroisoquinolinium derivatives as ligands of the apamin-sensitive Ca2+-activated K+ channels
Graulich, Amaury,Scuvée-Moreau, Jacqueline,Alleva, Livia,Lamy, Cédric,Waroux, Olivier,Seutin, Vincent,Liégeois, Jean-Fran?ois
, p. 7208 - 7214 (2007/10/03)
Several methoxylated 1,2,3,4-tetrahydroisoquinoliniums derived from N-methyl-laudanosine and N-methyl-noscapine were synthesized and evaluated for their affinity for apamin-sensitive binding sites. The quaternary ammonium derivatives have a higher affinit
TETRAHYDROISOQUINOLYL ACETAMIDE DERIVATIVES FOR USE AS OREXIN RECEPTOR ANTAGONISTS
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Page 22-23, (2008/06/13)
The invention relates to novel acetamide derivatives of formula (I) and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of such compound
Ruthenium dioxide in fluoro acid medium. III. Aplication to the synthesis of aporphinic, homoaporphinic and dibenzazocinic alkaloids. Studies towards the preparation of azafluoranthenic skeleton
Landais,Robin
, p. 7185 - 7196 (2007/10/02)
Intramolecular oxidative couplings of phenylalkyltetrahydroisoquinoline precursors in aporphinic and homoaporphinic alkaloids by using RuO2,2H2O in fluoro acidic media were performed. A comparative study of our reagent with TTFA has been made with different precursors. The procedure was also extended to the synthesis of one dibenzazocinic alkaloid. Then, we attempted to synthetize the azafluoranthenic ring, using phenolic and non phenolic isoquinoline precursors.
Oxidative Coupling of Phenols and Phenolic Ethers. Part 4. Synthesis of Dibenzazonines and a Dibenzazecine, via Direct Coupling
McDonald, Edward,Wylie, Robert D.
, p. 1104 - 1108 (2007/10/02)
Two series of amides, N-phenethylphenylacetamides (9) and the bisphenetylamides (11), including diphenolic monophenolic, and non-phenolic types, were treated with a range of one-electron oxidants.With the tetramethoxy-derivative (11e) intramolecular coupling yielded a dibenzazonine (16) in 36percent yield.Similar oxidation of the homologue (18) gave a dibenzazecine (19) in 60percent yield.
