cas 3506-36-3, 3-(DIMETHYLAMINO)-1-PHENYLPROPAN-1-ONE

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Derivatization of common antidepressant drugs increases inhibition of acid sphingomyelinase and reduces induction of phospholipidosis
In recent studies, major depressive disorder (MDD) was linked to an increase in acid sphingomyelinase (ASM) activity. Several drugs that are commonly used to treat MDD functionally inhibit the lysosomal enzyme ASM and are called functional inhibitors of ASM (FIASMAs). These drugs are classified as cationic amphiphilic drugs (CADs) that influence the catalytic activities of different lysosomal enzymes. This action results in the side effect of phospholipidosis (PLD), which describes a detrimental increase in the phospholipid content in lysosomes. FIASMAs differ only slightly in their physico-chemical properties, but their effects on ASM activity and induction of the lysosomal phospholipid content vary significantly. In this study, we systematically induced minor chemical modifications to the FIASMAs imipramine, desipramine and fluoxetine. We generated a library of 45 new CADs with slightly different log P (logarithmic partition coefficient) and pKa (logarithmic acid dissociation constant) values. The effects of the compounds on the ASM activity and lysosomal phospholipid content were assessed in cell culture assays. We identified four compounds with beneficial effects, i.e., increased ASM activity inhibition and reduced PLD induction compared with the original drugs. The compounds HT04, RH272B and RH272D outperformed the original imipramine, whereas RH281A performed better than desipramine. Thus, minor chemical variations of CADs impact lysosomal metabolism in a specific manner and can lead to antidepressant drugs with less deleterious side effects.
Rhein, Cosima,L?ber, Stefan,Gmeiner, Peter,Gulbins, Erich,Tripal, Philipp,Kornhuber, Johannes
p. 1837 - 1845
(2018)
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Metal-free synthesis of β-aminoketones by the reductive hydroamination of ynones
This study describes a cascade method for the synthesis of β-aminoketones through the reductive hydroamination of alkynes under very mild metal-free conditions. It allows for the rapid conversion of ynones and amines into corresponding β-aminoketones with a broad substrate scope and diverse functionalities. This straightforward and easy-to-handle reaction process can be successfully applied for the synthesis of Proroxan and Propipocaine, offering a potential option for the synthesis of drug molecules with the β-aminoketone skeleton.
Fu, Rui,Liu, Yu,Wu, Tao,Zhang, Xinyu,Zhu, Yang,Luo, Jiangbin,Zhang, Zhengyu,Jiang, Yaojia
supporting information
p. 3525 - 3528
(2022/03/31)

SMALL MOLECULE CMKLR1 ANTAGONISTS IN INFLAMMATORY DISEASE
α-NETA analogs are provided for the treatment of inflammatory disease.
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Paragraph 0199; 0230; 0232; 0241

(2020/12/01)

Design, synthesis and biological evaluation of novel triaryldimethylaminobutan-2-ol derivatives against Mycobacterium tuberculosis
Bedaquiline (TMC207), a typical diarylquinoline anti-tuberculosis drug, has been approved by FDA to specifically treat MDR-TB. Herein we describe design, synthesis, and in vitro biological evaluation against Mycobacterium tuberculosis of a series of triaryldimethylaminobutan-2-ol derivatives obtaining from the structural modification of TMC207. Compounds 23, 25, 28, 32, 39 and 43 provided superior anti-mycobacterial activity than positive control PC01 which shows the same configuration and contains TMC207. Compounds 16, 20, 29, 34, 37, 45 and 47 exhibited the similar activity to positive control PC01. Most importantly, the series of compounds showed excellent activity against XDR-Mtb. The result of acute toxicity suggested that this class of triaryldimethylaminobutan-2-ol derivatives should be graded as low. Further SAR analysis indicates that a large steric bulk of triaryl and 7-Br, 3-OCH3 on 1-naphthyl are critical.
Cao, Ruiyuan,Fan, Shiyong,Li, Song,Liu, Ping,Lu, Yu,Wang, Bin,Wang, Xiaokui,Zhong, Wu
(2020/07/13)

Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.
Lee, Melissa,Sanford, Melanie S.
supporting information
p. 572 - 575
(2017/02/10)

Iron-catalyzed oxyfunctionalization of aliphatic amines at remote benzylic C-H sites
We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp3)-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.
Mbofana, Curren T.,Chong, Eugene,Lawniczak, James,Sanford, Melanie S.
supporting information
p. 4258 - 4261
(2016/09/09)

A method for preparing optically active 3-amino-1-phenylpropanol derivatives as an intermediate and a method for preparing optically active pharmaceutical products using the same
The present invention relates to a method for preparing a 3-amino-1-phenylpropanol derivative having (R) or (S) optical activity with 80% or more of an enantiomeric excess (ee), which includes a step of performing an asymmetric reduction reaction in the presence of a spiroborate ester catalyst and a hydrogen donor. The invention also relates to a method for preparing an optically active pharmaceutical product, which includes a step of preparing a (R)- or (S)-3-amino-1-phenylpropanol derivative, that is an intermediate, by using the catalyst.(AA) 3-amino-1-phenylpropanol(BB) Tomoxetine(CC) Nisoxetine(DD) FluoxetineCOPYRIGHT KIPO 2016
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Paragraph 0105-0107

(2016/11/09)

DMF Dimethyl Acetal as Carbon Source for α-Methylation of Ketones: A Hydrogenation-Hydrogenolysis Strategy of Enaminones
A novel heterogeneous catalytic hydrogenation-hydrogenolysis strategy has been developed for the α-methylation of ketones via enaminones using DMF dimethyl acetal as carbon source. This strategy provides a very convenient route to α-methylated ketones using a variety of ketones without any base or oxidant. (Chemical Equation Presented).
Borah, Ashwini,Goswami, Limi,Neog, Kashmiri,Gogoi, Pranjal
p. 4722 - 4728
(2015/05/13)

GAMMA-DIKETONES AS WNT/BETA -CATENIN SIGNALING PATHWAY ACTIVATORS
The present disclosure provides γ-diketones or analogs thereof, that activate Wnt/β-catenin signaling and thus treat or prevent diseases related to signal transduction, such as osteoporosis and osteoarthropathy; osteogenesis imperfecta, bone defects, bone fractures, periodontal disease, otosclerosis, wound healing, craniofacial defects, oncolytic bone disease, traumatic brain injuries or spine injuries, brain atrophy/neurological disorders related to the differentiation and development of the central nervous system, including Parkinson's disease, strokes, ischemic cerebral disease, epilepsy, Alzheimer's disease, depression, bipolar disorder, schizophrenia; otic disorders like cochlear hair cell loss; eye diseases such as age related macular degeneration, diabetic macular edema or retinitis pigmentosa and diseases related to differentiation and growth of stem cell, such as hair loss, hematopoiesis related diseases and tissue regeneration related diseases.
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Paragraph 1714; 1715; 1716; 1717

(2014/09/03)

AROMATIC BUTAN-2-OL COMPOUNDS, PREPARATION METHODS AND USES THEREOF
The present invention relates to aromatic butan-2-ol compounds and preparation methods and uses thereof. Specifically, the present invention relates to the compound of Formula I, or an optical isomer, racemate, diastereomer, pharmaceutically acceptable salt or solvate thereof: wherein each of the substituents have the definitions as given in the specification. The present invention further relates to a pharmaceutical composition containing the compound, and the use of the compound in manufacture of a medicament for the treatment and/or prophylaxis of a disease or disorder caused by tubercle bacillus infection. The compound of Formula I of the present invention has advantages in treatment and/or prophylaxis of a disease or disorder caused by tubercle bacillus infection.
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Paragraph 0065; 0066; 0079; 0080

(2013/04/10)

Asymmetric hydrogenation of β-amino ketones with the bimetallic complex RuPHOX-Ru as the chiral catalyst
Asymmetric hydrogenations of a series of β-amino ketones were carried out with a bimetallic complex (RuPHOX-Ru) as the chiral catalyst. Almost all the reactions (performed in a mixed solvent system of toluene and H2O in the presence of KOH) gave quantitative conversions into their respective products with up to 99.9% ee. The RuPHOX-Ru catalyst is stable to both moisture and air. The procedure has the benefits of being inexpensive, environmentally friendly and highly efficient. Under a relatively low catalyst loading (TON = 2000), key intermediates of fluoxetine, tomoxetine and nisoxetine could be obtained in quantitative yield and in up to 99.9% ee. This methodology represents a promising alternative to the synthesis of the aforementioned drugs and their analogues. This journal is The Royal Society of Chemistry 2013.
Wang, Jiahao,Liu, Delong,Liu, Yangang,Zhang, Wanbin
supporting information
p. 3855 - 3861
(2014/03/21)

A novel method for biomimetic synthesis of Mannich bases
Since the early studies of Mannich, Mannich reaction has become an important tool for the synthesis of new compounds. Mannich bases can be either directly employed or used as intermediates. In this work, the one-carbon unit transfer reaction of tetrahydrofolate coenzyme was initiated. 1,3-Dimethylimidazolidine as a new tetrahydrofolate coenzyme model at formaldehyde oxidation level was used to react with ketone having active hydrogen atoms and amine to give the corresponding Mannich base in good yield by a covert Mannich reaction. A novel method for biomimetic synthesis of various Mannich bases is provided. 1,3-Dimethylimidazolidine as a new tetrahydrofolate coenzyme model at formaldehyde oxidation level was used to react with ketone having active hydrogen atoms and amine to give the corresponding Mannich base in good yield by a covert Mannich reaction. A novel method for biomimetic synthesis of various Mannich bases is provided. Copyright
Guo, Yuan,An, Jing,Lu, Zhenhuan,Peng, Mengjiao
experimental part
p. 1561 - 1564
(2012/10/07)

PROCESS FOR PREPARATION OF NORBORNENE DERIVATIVES
A method for producing a norbornene derivative, comprising: a first step of forming a Mannich base by reacting a carbonyl compound and an amine compound with each other in an acidic solvent, to thereby obtain a reaction liquid comprising the Mannich base in the acidic solvent, the acidic solvent comprising a formaldehyde derivative and 0.01 mol/L or more of an acid represented by the formula: HX (In the formula, X represents F or the like), the carbonyl compound being represented by any of the following general formulae (1) to (3): [in formulae (1) to (3), R1, R2, R3, R4, R5, and R6 each independently represent a hydrogen atom or the like, and n represents an integer of any of 0 to 4], the amine compound being represented by the following general formula (4): [in the formula (4), R7S each independently represent a linear chain saturated hydrocarbon group having 1 to 20 carbon atoms or the like, and X- represents F- or the like], the Mannich base being represented by any of the following general formulae (5) to (7): [R1, R2, R3, R4, R5, R6, and n in the formulae (5) to (7) have the same meanings as those of R1, R2, R3, R4, R5, R6, and n in the formulae (1) to (3), and R7 and X- in the formulae (5) to (7) have the same meanings as those of R7 and X- in the formula (4)] and a second step of reacting the Mannich base and a diene compound with each other by adding an organic solvent, a base in an amount of 1.0 to 20.0 equivalents to the acid, and the diene compound to the reaction liquid, and then heating the reaction liquid, to thereby form a norbornene derivative, the diene compound being represented by the following general formula (8): [in the formula (8), R8 represents a hydrogen atom or the like], the norbornene derivative being represented by any of the following general formulae (9) to (11): [R1, R2, R3, R4, R5, R6, and n in the formulae (9) to (11) have the same meanings as those of R1, R2, R3, R4, R5, R6, and n in the formulae (1) to (3), and R8 in the formulae (9) to (11) has the same meaning as that of R8 in the formula (8)].
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Page/Page column 27-28

(2012/05/04)

CYCLIC INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE 1 BASED ON THE 1,3 -OXAZINAN- 2 -ONE STRUCTURE
This invention relates to substitued 1, 3-oxazin-2-one compounds of the Formula (I), (II), (IIA), (IIB), (IIC), (II D), (IIE), (III), (III A), (III B), (IV), (IV A), (IV B), (IV C), (IV D), (V), (V A), (V B), (VI), (VI A), (VI B), (VII), (VII A), (VII B), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11β-HSD1 in mammals. The invention further relates to pharmaceutical compositions of the novel compounds and methods for their use in the reduction or control of the production of Cortisol in a cell or the inhibition of the conversion of cortisone to Cortisol in a cell.
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Page/Page column 92-93

(2011/02/24)

Structure-based design and synthesis of 1,3-oxazinan-2-one inhibitors of 11β-hydroxysteroid dehydrogenase type 1
Structure based design led directly to 1,3-oxazinan-2-one 9a with an IC50 of 42 nM against 11β-HSD1 in vitro. Optimization of 9a for improved in vitro enzymatic and cellular potency afforded 25f with IC 50 values of 0.8 nM for the enzyme and 2.5 nM in adipocytes. In addition, 25f has 94% oral bioavailability in rat and >1000× selectivity over 11β-HSD2. In mice, 25f was distributed to the target tissues, liver, and adipose, and in cynomolgus monkeys a 10 mg/kg oral dose reduced cortisol production by 85% following a cortisone challenge.
Xu, Zhenrong,Tice, Colin M.,Zhao, Wei,Cacatian, Salvacion,Ye, Yuan-Jie,Singh, Suresh B.,Lindblom, Peter,McKeever, Brian M.,Krosky, Paula M.,Kruk, Barbara A.,Berbaum, Jennifer,Harrison, Richard K.,Johnson, Judith A.,Bukhtiyarov, Yuri,Panemangalore, Reshma,Scott, Boyd B.,Zhao, Yi,Bruno, Joseph G.,Togias, Jennifer,Guo, Joan,Guo, Rong,Carroll, Patrick J.,McGeehan, Gerard M.,Zhuang, Linghang,He, Wei,Claremon, David A.
supporting information; experimental part
p. 6050 - 6062
(2011/10/31)

Superelectrophilic chemistry of amino-nitriles and related substrates
The superacid-promoted Houben/Hoesch reactions of amino-nitriles and related compounds have been studied. The nitriles form dicationic electrophiles and react with benzene in fair to good yields (12-95%). The intermediate iminium ions may also be reduced to the benzylic amines by NaBH4 or H 2.
Raja, Erum K.,Klumpp, Douglas A.
experimental part
p. 4494 - 4497
(2011/07/08)

Antimalarial versus cytotoxic properties of dual drugs derived from 4-aminoquinolines and mannich bases: Interaction with DNA
The synthesis and biological evaluation of new organic and organometallic dual drugs designed as potential antimalarial agents are reported. A series of 4-aminoquinoline-based Mannich bases with variations in the aliphatic amino side chain were prepared via a three-steps synthesis. These compounds were also tested against chloroquine-susceptible and chloroquine-resistant strains of Plasmodium falciparum and assayed for their ability to inhibit the formation of β-hematin in vitro using a colorimetric β-hematin inhibition assay. Several compounds showed a marked antimalarial activity, with IC50 and IC90 values in the low nM range but also a high cytotoxicity against mammalian cells, in particular a highly drug-resistant glioblastoma cell line. The newly designed compounds revealed high DNA binding properties, especially for the GC-rich domains. Altogether, these dual drugs seem to be more appropriate to be developed as antiproliferative agents against mammalian cancer cells than Plasmodium parasites.
Tóth, Katalin,Wenzel, Nicole I.,Chavain, Natascha,Wang, Yulin,Friebolin, Wolfgang,Maes, Louis,Pradines, Bruno,Lanzer, Michael,Yardley, Vanessa,Brun, Reto,Herold-Mende, Christel,Biot, Christophe,Davioud-Charvet, Elisabeth
body text
p. 3214 - 3226
(2010/10/19)

Asymmetric synthesis of α-N,N-dialkylamino alcohols by transfer hydrogenation of N,N-dialkylamino ketones
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Kosmalski, Tomasz
experimental part
p. 717 - 721
(2011/05/14)

CYCLIC INHIBITORS OF 11β-HYDROXYSTERIOD DEHYDROGENASE 1
This invention relates to novel compounds of the Formula (I), (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih); (Ii); (Ij), (Ik), (II) pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11 β-HSD1 in mammals. The invention further relates to pharmaceutical compositions of the novel compounds and methods for their use in the reduction or control of the production of cortisol in a cell or the inhibition of the conversion of cortisone to cortisol in a cell.
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Page/Page column 148

(2009/03/07)

Design of tRNALys3 Ligands: Fragment evolution and linker selection guided by NMR spectroscopy
A fragment-based approach for the synthesis of ligands of tRNA Lys3, the HIV reverse-transcription primer, is described. The use of NMR spectroscopy has proved to be very useful in this approach, not only to detect lowaffinity complexes between small compounds and RNA, but also to provide information on their binding mode and on the way they can be connected. This NMR-spectroscopy-guided analysis enabled us to design micromolar ligands after the optimisation and connection of millimolar fragments with an appropriate linker. The influence of the linker region on the binding affinity and selectivity outlines the importance of having a flexible assemblage strategy with a variety of linkers in such an approach. 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Chung, Florence,Tisne, Carine,Lecourt, Thomas,Seijo, Bili,Dardel, Frederic,Micouin, Laurent
scheme or table
p. 7108 - 7116
(2010/04/05)

Scaffold oriented synthesis. Part 2: Design, synthesis and biological evaluation of pyrimido-diazepines as receptor tyrosine kinase inhibitors
We report the discovery of the pyrimido-diazepine scaffolds as novel adenine mimics. Structure-based design led to the discovery of analogs with potent inhibitory activity against receptor tyrosine kinases, such as KDR, Flt3 and c-Kit. Compound 14 exhibited low nanomolar KDR enzymatic and cellular potencies (IC50 = 9 and 52 nM, respectively).
Gracias, Vijaya,Ji, Zhiqin,Akritopoulou-Zanze, Irini,Abad-Zapatero, Cele,Huth, Jeffrey R.,Song, Danying,Hajduk, Philip J.,Johnson, Eric F.,Glaser, Keith B.,Marcotte, Patrick A.,Pease, Lori,Soni, Nirupama B.,Stewart, Kent D.,Davidsen, Steven K.,Michaelides, Michael R.,Djuric, Stevan W.
p. 2691 - 2695
(2008/12/21)

Asymmetric Michael addition of α-nitro-ketones using catalytic peptides
Peptide-based catalysts have been developed that promote the asymmetric Michael addition of nitroalkanes. The most effective peptides contain a β-turn structural element as well as a basic histidine and an arylsulfonamide-protected arginine. Excellent yields with enantioselectivities of up to 74% ee have been observed.
Linton, Brian R.,Reutershan, Michael H.,Aderman, Christopher M.,Richardson, Elizabeth A.,Brownell, Kristen R.,Ashley, Charles W.,Evans, Catherine A.,Miller, Scott J.
p. 1993 - 1997
(2007/10/03)

NMR-guided fragment-based approach for the design of tRNALys3 ligands
Two in one: Two ligands for tRNALys3 that were identified from a compound library by flow-injection NMR spectroscopic screening and found to have millimolar dissociation constants (on the left in the picture) inspired the fragment-based synthesis of a new family of ligands with the general structural features of both initial compounds. Ligand 1 of this family is a selective D-stem binder of tRNALys3 with a micromolar Kd value.
Chung, Florence,Tisne, Carine,Lecourt, Thomas,Dardel, Frederic,Micouin, Laurent
p. 4489 - 4491
(2008/03/27)

INHIBITORS OF AKT ACTIVITY
Invented are novel 1 H-imidazo[4,5-c]pyridin-2-yl compounds, the use of such compounds as inhibitors of protein kinase B activity and in the treatment of cancer and arthritis.
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Page/Page column 139

(2008/06/13)

Pulmonary delivery for bioconjugation
Methods of and compositions for pulmonary delivery of therapeutic agents which are capable of forming covalent bonds with a site of interest or which have formed a covalent bond with a pulmonary solution protein are disclosed. Therapeutic agents useful in the invention include wound healing agents, antibiotics, anti-inflammatories, anti-oxidants, anti-proliferatives, immunosupressants, anti-infective and anti-cancer agents.
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(2008/06/13)

DIARYL ETHERS AS OPIOID RECEPTOR ANTAGONIST
A compound of the formula (I) wherein the variables X1 to X10, R1 to R7 including R3', E, v, y, z, A and B are as described, or a pharmaceutically acceptable salt, solvate, enantiomer, racemate, diastereomer or mixtures thereof, useful for the treatment, prevention or amelioration of obesity and Related Diseases is disclosed.
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Page/Page column 70-71

(2008/06/13)

Pyrazoline derivative or tetrahydropyridazine derivative and medicinal use thereof
Using a compound selected from compounds represented by the following formula (1) (which include 3-phenyl-2-pyrazoline derivatives and 3-phenyl-tetrahydropyridazine derivatives) and pharmacologically acceptable salts thereof, an agent is provided which can activate glutamic acid transporter and which is useful for prevention and/treatment of cerebral ischemia (cerebral infarct and brain edema), amyotrophic lateral sclerosis (ALS), etc., all caused by glutamic acid toxicity.
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(2008/06/13)

Dutch Resolution: Separation of enantiomers with families of resolving agents. A status report
Dutch Resolution is the term given to the use of mixtures (families) of resolving agents in classical resolutions. In this status report an overview is given of the latest results and new (possible) families of resolving agents are introduced. The concept of families is discussed as well as the factors that come into play on use of families. Practical aspects of Dutch Resolution in particular and resolutions in general are discussed.
Kellogg, Richard M.,Nieuwenhuijzen, Jose W.,Pouwer,Vries, Ton R.,Broxterman, Quirinus B.,Grimbergen, Reinier F.P.,Kaptein, Bernard,La Crois, Rene M.,De Wever, Ellen,Zwaagstra, Karen,Van Der Laan, Alexander C.
p. 1626 - 1638
(2007/10/03)

Anticonvulsant activity of semicarbazone derivatives of Mannich bases
A series of semicarbazones of semicarbazide/p-chlorophenyl semicarbazide and Mannich bases of acetophenone/p-chloroacetophenone has been synthesized and their anticonvulsant activity screened against MES and scPTZ test. p-Chlorophenyl semi-carbazone of N,N-dimethylaminopropiophenone has been found to be the most active in all these tests.
Pandeya,Sowmyalakshmi,Panda,Pandeya,Stables
p. 2657 - 2661
(2007/10/03)

Novel domino products from the reaction of phenyl vinyl ketone and its derivatives with cyclic ketones
Reaction of phenyl vinyl ketone with cyclopentanone under thermal conditions resulted in novel domino products, 1,5,9-triketones along with the expected 1,5-diketones. The 1,5,9-triketones were formed via a Michael-Michael-rearrangement pathway. On the other hand, reaction under basic conditions furnished a spiro[4.5]decanone, formed by domino pathways involving Michael-Michael-aldol condensation reactions. Microwave mediated reductive amination-cyclization of the 1,5,9-triketone furnished the perhydrocyclopenta[ij]quinolizine derivative.
Surya Prakash Rao,Jeyalakshmi,Senthilkumar
p. 2189 - 2199
(2007/10/03)

Simple synthetic equivalents for the β-(N,N-disubstituted)ethylamino acyl cation synthon and their applications
Various N,N-disubstituted-β-amino-N-methoxy-N-methylpropanamides 3a-i were prepared which served as an excellent β-aminoacyl cation equivalents. These were used to prepare β-amino ketones 1, pharmacologically active tertiary 1-(3,3-diarylpropyl)amines 7a-c, and the interesting C-glycoside 8.
Selvamurugan,Aidhen
p. 2239 - 2246
(2007/10/03)

A convenient alternative route to β-aminoketones
Enaminones has been prepared and submitted to conjugate reduction with LAH and the system Al2O3/R2NH to give β-aminoketones. The latter tandem amination system has also been applied in the Mannich reaction, improving the synthesis of several new diaryl β-aminoketones. Besides, the sequential use of DMFDMA and LAH-CuI on deoxybenzoins furnishes a new route for the synthesis of enones.
San Martin,De Marigorta,Dominguez
p. 2255 - 2264
(2007/10/02)

Development and Application of a Continuous Microwave Reactor for Organic Synthesis
A laboratory-scale continuous microwave reactor (CMR) has been developed and used to conduct organic syntheses routinely, rapidly, and safely in a range of solvents, under pressures up to 1400 kPa and at temperatures up to 200 deg C.Advantages and applications of the CMR are discussed, along with the rationale for the design.Reactions carried out with the CMR included nucleophilic substitution, addition, esterification, transesterification, acetalization, amidation, base- and acid-catalyzed hydrolysis, isomerization, decarboxylation, and elimination.Name reactions included the Michael addition, Hofmann degradation, Williamson ether synthesis, and the Mannich, Finkelstein, Baylis-Hillman, and Knoevenagel reactions.
Cablewski, Teresa,Faux, Alan F.,Strauss, Christopher R.
p. 3408 - 3412
(2007/10/02)

Aryl and ethoxycarbonyl derivatives of pyrroles, 2H pyrroles and 3,4-dihydropyrroles and their immunoactivity of human T lymphocytes
Several pyrroles, 2H pyrroles, 3,3-dihydropyrroles substituted in various positions with phenyl and ethoxycarbonyl groups, were prepared in order to study in vitro their immunoactivity on human T lymphocytes. The best action was observed when on the pyrrole cycle, a carboxylic chain in position 2, an aromatic cycle in 5, and a substituent in 3, particularly a phenyl or a carboxylic ester were simultaneously found to exist. A conformational approach, performed by magnetic anisotropy quantification of phenyls, using Johnson and Bovey increments, showed that the orthogonality of the substituent in 3 is important as regards the pyrrolic cycle. Thus, the ethyl 3,5-diphenylpyrrole-2-carboxylate ester 8 appears to be the most interesting as it is more efficient than the levamisole chlorhydrate in the tests connected with the lymphoblastic transformation in presence of PHA (phyto-hemagglutinin) and related to the mobilisation of CD2 receptors.
Birouk,Harraga,Panouse-Perrin,Robert,Damelincourt,Theobald,Mercier,Panouse
p. 91 - 99
(2007/10/02)

Mannich Reaction of Carbonyl Compounds via Boron Enolates and N,N,N',N'-Tetramethyldiaminomethane
A variety of carbonyl compounds undergo N,N-dimethylaminomethylation in moderate to good yields by the Mannich reaction involving boron enolates and N,N,N',N'-tetramethyldiaminomethane in dichloromethane.
Nolen, Ernest G.,Allocco, Andrea,Vitarius, Jim,McSorley, Karen
p. 1532 - 1533
(2007/10/02)

SUBSTITUTED PHENOXYPHENYLPROPLY DIMETHYLAMINES
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(2008/06/13)

Treatment of obesity with aryloxyphenylpropylamines
3-Aryloxy-3-phenylpropylamines and acid addition salts thereof are useful in blocking uptake of monoamines by brain neurons, and are thus effective in treating disorders of sleep, sexual performance, appetite, muscular function, and pituitary function.
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(2008/06/13)

KINETICS AND MECHANISM OF REACTION OF AMINES WITH β-BROMOPROPIOPHENONE
The reaction of β-bromopropiophenone with different amines in acetonitrile at 25 deg C was studied.It was found that in the case of primary and secondary amines, the end products of the reaction are β-aminopropiophenones, which form via the intermediate phenyl vinyl ketone.In the case of tertiary amines, the reaction ends at the stage of the formation of phenyl vinyl ketone.The reactivity of the amines in the formation of phenyl vinyl ketone is preferentially determined by their basicity.
Popov, A. F.,Piskunova, Z.,Matvienko, V. N.
p. 1299 - 1302
(2007/10/02)

Synthesis and pharmacologic activity of derivatives of 3-aminopropiophenone and 3-aminomethylcamphor
As a part of a research on analgesic compounds 0-(4-methoxyphenyl)carbamoyl-3-aminopropiophenone oximes, 0-(4-methoxyphenyl)-carbamoyl-3-aminomethylcamphor oximes and 4-(4-methoxyphenyl)semicarbazones of 3-aminopropiophenones were prepared. The analgesic activity of these compounds was tested and the results of pharmacological screening are discussed.
Occelli,Fontanella,Diena,Schiatti
p. 86 - 101
(2007/10/02)

Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C1 Unit. III. A Convenient Synthesis of the Mannich Base from Enol Silyl Ether by a Combination of Chloroiodomethane and N,N,N',N'-Tetramethylmethanediamine
The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via enol trimethylsilyl ethers by a combination of chloroiodomethane (CH2ClI) and N,N,N',N'-tetramethylmethanediamine (TMMD) in DMSO as the solvent at ambient temperatute.The mechanism of the transformation is discussed on the basis of product analysis and 1H NMR spectral studies.The reagent system CH2ClI/TMMD also provides a convenient route to the Eschenmoser's salt ().
Miyano, Sotaro,Hokari, Hiroshi,Hashimoto, Harukichi
p. 534 - 539
(2007/10/02)

THE MANNICH REACTION OF CARBONYL COMPOUNDS VIA SILYL ENOL ETHERS BY A COMBINATION OF CHLOROIODOMETHANE AND N,N,N',N'-TETRAMETHYLDIAMINOMETHANE
The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via trimethylsilyl enol ethers by a combination of chloroiodomethane and N,N,N',N'-tetramethyldiaminomethane in DMSO or DMF as the solvent at ambient temperature.
Miyano, Sotaro,Hokari, Hiroshi,Mori, Akira,Hashimoto, Harukichi
p. 1213 - 1214
(2007/10/02)

Aryloxyphenylpropylamines in treating depression
3-Aryloxy-3-phenylpropylamines and acid additions salts thereof, useful as psychotropic agents, particularly as anti-depressants.
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(2008/06/13)