59192-94-8Relevant academic research and scientific papers
Convenient Route to 2-(Trialkylstannyl)cyclopropylamines and Their Application in Palladium-Catalyzed Cross-Coupling Reactions
Wiedemann, Stefan,Rauch, Karsten,Savchenko, Andrei,Marek, Ilan,De Meijere, Armin
, p. 631 - 635 (2004)
The 2-(trialkylstannyl)-N,N-dialkylcyclopropylamines 3 were obtained by titanium-mediated aminocyclopropanation of tributylvinylstannane with N,N-dialkylformamides in yields of 80-84% and with excellent diastereoselectivities (trans/cis > 45:1). The resulting stannanes could advantageously be applied in Stille cross-coupling reactions with aryl iodides, providing the pure trans-2-aryl-(N,N-dialkylamino)cyclopropanes 8 in yields ranging from 45 to 67% (six examples). The coupling of ethyl (E)-3-iodoacrylate (9) gave ethyl cis-5-(dibenzylamino)cyclopent-2-enecarboxylate (10) as a single diastereomer in 54% yield. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Electrophilic Zinc Homoenolates: Synthesis of Cyclopropylamines from Cyclopropanols and Amines
Mills, L. Reginald,Barrera Arbelaez, Luis Miguel,Rousseaux, Sophie A. L.
supporting information, p. 11357 - 11360 (2017/08/30)
Metal homoenolates, produced via C-C bond cleavage of cyclopropanols, have been extensively investigated as nucleophiles for the synthesis of β-substituted carbonyl derivatives. Herein, we demonstrate that zinc homoenolates can react as carbonyl-electrophiles in the presence of nucleophilic amines to yield highly valuable trans-cyclopropylamines in good yields and high diastereoselectivities. GSK2879552, a lysine demethylase 1 inhibitor currently in clinical trials for the treatment of small cell lung carcinoma, was synthesized using this strategy.
Selective 5-hydroxytryptamine 2c receptor agonists derived from the lead compound tranylcypromine: Identification of drugs with antidepressant-like action
Sung, Jin Cho,Jensen, Niels H.,Kurome, Toru,Kadari, Sudhakar,Manzano, Michael L.,Malberg, Jessica E.,Caldarone, Barbara,Roth, Bryan L.,Kozikowski, Alan P.
experimental part, p. 1885 - 1902 (2009/12/07)
We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2- phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted be zene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT 2A and 5-HT2B, respectively (EC50) 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.
5-HT2C RECEPTOR AGONISTS AS ANORECTIC AGENTS
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Page/Page column 35; 77, (2008/06/13)
This invention relates to compounds which modulate receptors of the 5-HT2 family of receptors, and particularly to compounds which modulate 5-HT2C receptors. Compounds of the invention include agonists and selective agonists for the 5-HT2C receptor. Compounds of the invention include selective agonists for the 5-HT2C receptor which exhibit significantly less or no agonist activity on the 5-HT2A receptor and/or the 5-HT2B receptor. Compounds of this invention are those of Formula I and pharmaceutically acceptable salts, esters and solvates (including hydrates) wherein variables are defined in the specification hereof.
