- Design, Synthesis, and Structure-Activity Relationship Studies of Novel Indolyalkylpiperazine Derivatives as Selective 5-HT1A Receptor Agonists
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5-HT1A receptor (5-HT1AR) agonists have been implicated in the treatment of a variety of central nervous system (CNS) diseases such as depression and anxiety, et al. Based on our previously found compound FW01 (Ki = 51 ± 16 nM) obtained by virtual screening, a series of FW01 derivatives were designed and synthesized by the modification of the amide tail group as well as indole headgroup of FW01. SAR exploration found that amide tail group and indole headgroup play pivotal roles in determining the binding affinity and selectivity on dopamine and serotonin receptor subtypes. Among all tested compounds, 9_24 has a Ki value of 5 ± 0.6 nM with a good selectivity toward 5-HT1AR. The [35S] GTPγS assay showed that 9_24 is a full agonist toward 5-HT1AR with an EC50 value of 0.059 nM, which shows 266.2 and 146.4-fold selectivity to 5-HT2A and D3 respectively. Molecular dynamics simulations and molecular docking studies with 5-HT1AR-9_24 were performed to disclose the mechanism of its high activity and selectivity. Finally, a detailed stepwise 9_24 induced signal transduction mechanism of 5-HT1AR is proposed.
- Wang, Wenli,Zheng, Lan,Li, Wei,Zhu, Chen,Peng, Weiqing,Han, Bing,Fu, Wei
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p. 235 - 248
(2020/02/18)
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- Titanium-Catalyzed Hydroaminoalkylation of Ethylene
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The first examples of titanium-catalyzed hydroaminoalkylation reactions of ethylene with secondary amines are presented. The reactions can be achieved with various titanium catalysts and they do not require the use of high pressure equipment. In addition, the first solid-state structure of a titanapyrrolidine that is formed by insertion of an alkene into the Ti?C bond of a titanaaziridine is reported.
- Rosien, Michael,T?ben, Iris,Schmidtmann, Marc,Beckhaus, Rüdiger,Doye, Sven
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supporting information
p. 2138 - 2142
(2020/02/05)
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- Stable preformed chiral palladium catalysts for the one-pot asymmetric reductive amination of ketones
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(Chemical Equation Presented) The application of air stable preformed [(R)-BINAP]PdBr2, [(S)-BINAP]PdBr2, [(R)-Tol-BINAP] PdBr2, and [(S,S)-CHIRAPHOS]PdBr2 complexes in the one-pot asymmetric reductive amination
- Rubio-Perez, Laura,Javier Perez-Flores,Sharma, Pankaj,Velasco, Luis,Cabrera, Armande
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supporting information; experimental part
p. 265 - 268
(2009/08/08)
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- Secondary amine formation from reductive amination of carbonyl compounds promoted by lewis acid using the InCl3ZEt3SiH system
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A robust and reliable method has been developed for reductive amination of primary amines with various aldehydes and ketones using Zn(ClO4) 2.6H20 as a catalyst. [In-H] generated in situ via a combination of InCl3 and Et3SiH is employed as an effective reducing system. A variety of secondary amines can be synthesized in a one-pot procedure in excellent yields.
- Lee, On-Yi,Law, Ka-Lun,Yang, Dan
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supporting information; experimental part
p. 3302 - 3305
(2009/11/30)
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- Direct reductive amination of carbonyl compounds with primary/secondary amines using recyclable water-soluble FeII/EDTA complex as catalyst
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Direct reductive amination of aliphatic, aromatic and heterocyclic carbonyl compounds with primary/secondary amines is reported with water-soluble FeII/EDTA complex as a catalyst using low-pressure molecular hydrogen in a biphasic media. The catalyst is highly selective, recyclable and is an excellent replacement for expensive noble metal catalysts or stoichiometric reducing agents.
- Bhor, Malhari D.,Bhanushali, Mayur J.,Nandurkar, Nitin S.,Bhanage, Bhalchandra M.
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p. 965 - 969
(2008/09/17)
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- Direct reductive amination of carbonyl compounds using bis(triphenylphosphine) copper(I) tetrahydroborate
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A direct reductive amination protocol for aldehydes/ketones using bis(triphenylphosphine) copper(I) tetrahydroborate as a novel reducing agent in the presence of sulfamic acid has been developed. The reagent chemoselectively reduces the imine moiety and does not affect other reducible functionalities such as chloro, nitro, cyano and methoxy.
- Bhanushali, Mayur J.,Nandurkar, Nitin S.,Bhor, Malhari D.,Bhanage, Bhalchandra M.
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p. 1273 - 1276
(2007/10/03)
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- Addition of trialkylalanes to imines under zirconium catalysis
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Trialkylalanes, which are inert toward imines, undergo addition to them in the presence of a catalytic amount of dichlorodicyclopentadienylzirconium(IV) (Cp2ZrCl2). The reaction tolerates the presence of several functional groups in the starting imine such as halo, amide, nitrile, and hydroxy groups. A possible reaction pathway is proposed involving metallacyclic intermediates. Georg Thieme Verlag Stuttgart.
- Denhez, Clement,Vasse, Jean-Luc,Szymoniak, Jan
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p. 2075 - 2079
(2007/10/03)
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- Reductions of C=O and C=N groups with the systems composed of (η5-C5H5)2MoH2 and acids
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Selective reductions of organic compounds, such as carbonyl compounds and imines, using a system composed of Cp2MoH2 and acids are examined. This system can reduce the substrates under mild conditions. Extremely high diastereoselectivity was achieved in the reduction of 4-t-butylcyclohexanone. The reactivity of imines depends on their structure. Aromatic imines are found to be more reactive than aliphatic imines.
- Minato, Makoto,Fujiwara, Yutaka,Koga, Miho,Matsumoto, Naoya,Kurishima, Susumu,Natori, Makoto,Sekizuka, Norihiro,Yoshioka, Ken-Ichiro,Ito, Takashi
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p. 139 - 145
(2007/10/03)
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- Sodium borohydride on wet clay: Solvent-free reductive amination of carbonyl compounds using microwaves
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A solvent-flee reductive amination of carbonyl compounds by wet montmorillonite K 10 clay supported sodium borohydride is described; microwave irradiation facilitates the procedure.
- Varma, Rajender S.,Dahiya, Rajender
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p. 6293 - 6298
(2007/10/03)
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- Reduction of imines to amines through use of Cp2MoH2 and protonic acid system
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Imines are conveniently reduced to the corresponding amines by molybdenum dihydride CpMoH2 under mild conditions in good yields.In the presence of a ketone only an imine was reduced and the ketone was recovered quantitatively.
- Minato, Makoto,Fujiwara, Yutaka,Ito, Takashi
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p. 647 - 648
(2007/10/02)
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- A simple method for preparation of secondary aromatic amines
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A simple and efficient method for the preparation of secondary N-alkylarylamines via reductive amination of ketones with primary aromatic amines using activated zinc/acetic acid is described. It requires only equimolar amounts of the starting compounds and affords good yields of the corresponding amines (50-90%). It is not applicable to aldehydes nor aliphatic amines.
- Micovic,Ivanovic,Piatak,Bojic
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p. 1043 - 1045
(2007/10/02)
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- A New Synthesis of Imines via Grignard- and Cuprate Additions to N-Trimethylsilylformamides
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Various imines and some amines were synthesized by the addition of Grignard reagents, homo- and hetero-cuprates to N-silylated-, N-alkyl-, or N-arylformamides 1.
- Feringa, Ben L.,Jansen, Johan F. G. A.
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p. 184 - 186
(2007/10/02)
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- Reduction of Schiff Bases with Isopropyl Alcohol and Aluminum Isopropoxide in the Presence of Raney Nickel
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The reduction of several N-alkyl and N-aryl ketimines to the corresponding secondary amines is described.The reaction, which generally proceeds in high yield, is effected by isopropyl alcohol and aluminium isopropoxide in the presence of Raney nickel.In the absence of the nickel catalyst, that is, under the Meerwein-Ponndorf-Verley conditions, the reaction takes a different route and N-isopropylamines are formed at preference to the direct reduction products.Without the aluminum alkoxide the reduction proceeds only for a small percentage.This reaction, besides offering a new method for the synthesis of secondary amines, represents the first example where the couple aluminum alkoxide/Raney nicel is used in catalytic transfer hydrogenation reactions.
- Botta, Maurizio,Angelis, Francesco De,Gambacorta, Augusto,Labbiento, Lucia,Nicoletti, Rosario
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p. 1916 - 1919
(2007/10/02)
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