- KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones
-
An efficient and simple KOt-Bu-promoted selective ring-opening N-alkylation of 2-methyl-2-oxazoline or 2-(methylthio)-4,5-dihydrothiazole with benzyl halides under basic conditions is described for the first time. The method provides a convenient and practical pathway for the synthesis of versatile 2-aminoethyl acetates and N-substituted thiazolidinones with good functional group tolerance and selectivity. KOt-Bu not only plays an important role to promote this ring-opening N-alkylation, but also acts as an oxygen donor.
- Li, Bin,Lin, Qiao,Zhang, Shiling
-
-
Read Online
- Copper(I) chloride-catalyzed three-component coupling reaction of primary amines with electrophiles and α-halogen-substituted allylsilanes to form unsymmetrical tertiary amines
-
Tertiary amines with three different substituents, in one of which a vinylsilane functionality was included, were straightforwardly formed by the copper(I) chloride-catalyzed tandem reaction of primary amines, α-halogen-substituted allylsilanes, and electrophiles such as electron-deficient olefins, alkyl halides, alkyl tosylates, or epoxides. In the case using electron-deficient olefins as the electrophile, the addition of chloroacetone to the reaction system afforded the three-component coupling reaction more effectively. The addition of trimethyl borate as a co-catalyst improved the yields of the three-component coupling products in the reaction using alkyl halides, alkyl tosylates, or epoxides as the electrophiles, although the reaction times were lengthened.
- Kozuka, Makoto,Inoue, Akihiko,Tsuchida, Teruko,Mitani, Michiharu
-
-
Read Online
- Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids
-
For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in C?C bond-forming hydrogen-borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub-stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleaved in one pot to give γ-aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may be performed in sequence without isolation of the hydrogen-borrowing intermediate, removing the need for column chromatography.
- Hall, Christopher J. J.,Goundry, William R. F.,Donohoe, Timothy J.
-
supporting information
p. 6981 - 6985
(2021/03/01)
-
- GAS TREATING SOLUTIONS CONTAINING IMIDAZOLE-AMINE COMPOUNDS AND METHODS OF MAKING THE SAME
-
Systems comprising a composition where an imidazole is tethered to an amine and a solvent are described herein. Methods of their preparation and use are also described herein. The methods of using the systems include the reduction of volatile compounds from gas streams and a liquid stream.
- -
-
Paragraph 0202
(2021/12/03)
-
- A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides
-
Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.
- Kaicharla, Trinadh,Ngoc, Trung Tran,Teichert, Johannes F.,Tzaras, Dimitrios-Ioannis,Zimmermann, Birte M.
-
supporting information
p. 16865 - 16873
(2021/10/20)
-
- Manganese-catalysed transfer hydrogenation of esters
-
Manganese catalysed ester reduction using ethanol as a hydrogen transfer agent in place of dihydrogen is reported. High yields can be achieved for a range of substrates using 1 mol% of a Mn(i) catalyst, with an alkoxide promoter. The catalyst is derived from a tridentate P,N,N ligand.
- Oates, Conor L.,Widegren, Magnus B.,Clarke, Matthew L.
-
supporting information
p. 8635 - 8638
(2020/08/21)
-
- Preparation method of amino polyethylene glycol propionic acid
-
The invention relates to the field of organic synthesis, in particular to a preparation method of amino polyethylene glycol propionic acid. The preparation method comprises the steps that catalytic hydrogenation is carried out on dibenzyl amino polyethylene glycol tert-butyl propionate shown in formula I-2 to obtain amino polyethylene glycol tert-butyl propionate shown in formula I-3; (2) the amino polyethylene glycol tert-butyl propionate shown in formula I-3 is hydrolyzed under the acidic condition to obtain amino polyethylene glycol propionic acid shown in formula I. The preparation methodof the amino polyethylene glycol propionic acid has the advantages that the defects in the prior art that the yield is low, the dangerousness is high, and the enlargement of production is difficult are overcome, the reaction conditions are mild, the operation is simple, an intermediate does not to be purified, the next reaction can be directly carried out, the whole yield reaches up to 87-92%, thepurity of end products reaches up to 97-99.5%, and a safe and efficient synthetic route is provided for the preparation of amino polyethylene glycol propionic acid.
- -
-
Paragraph 0076; 0077; 0085; 0086; 0095; 0096
(2019/01/14)
-
- Cs2CO3-Promoted Direct N-Alkylation: Highly Chemoselective Synthesis of N-Alkylated Benzylamines and Anilines
-
Herein is described an efficient and chemoselective method for the synthesis of diversely substituted secondary amines in yields up to 98 %. Direct mono-N-alkylation of primary benzylamines and anilines with a wide range of alkyl halides is promoted by a cesium base in the absence of any additive or catalyst. The basicity and solubility of cesium carbonate in anhydrous N,N-dimethylformamide not only enables mono-N-alkylation of primary amines but also suppresses undesired dialkylation of the desired amines.
- Castillo, Juan-Carlos,Orrego-Hernández, Jessica,Portilla, Jaime
-
p. 3824 - 3835
(2016/08/20)
-
- AZACARBAZOLE BTK INHIBITORS
-
The present invention provides Bruton's Tyrosine Kinase (Btk) inhibitor compounds according to Formula (I), or pharmaceutically acceptable salts thereof, wherein CH, R1, R1a, R1b, R2, R3, and the subscripts m1, m2, p, q, and t are as set forth herein. The present invention also provides pharmaceutical compositions comprising these compounds and their use in therapy. In particular, the present invention relates to the use of Btk inhibitor compounds of Formula (I) in the treatment of Btk mediated disorders.
- -
-
Page/Page column 57
(2016/10/31)
-
- ERK INHIBITORS
-
The present invention provides thieno[2,3-c]pyrrol-4-one compounds that inhibit activity of extracellular-signal-regulated kinase (ERK) and may be useful in the treatment of cancer.
- -
-
Paragraph 0119
(2016/07/27)
-
- Novel dihydroquinolizinones for the treatment and prophylaxis of hepatitis B virus infection
-
The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds.
- -
-
Paragraph 1850; 1851
(2015/08/04)
-
- NOVEL DIHYDROQUINOLIZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION
-
The invention provides novel compounds having the general formula (I) wherein R1, R2 R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds in the treatment of the hepatitis B virus.
- -
-
Page/Page column 281
(2015/09/23)
-
- BROMODOMAIN-INHIBITING COMPOUNDS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME FOR PREVENTING OR TREATING A CANCER
-
Provided is a novel compound having bromodomain and extra terminal domain (BET) protein inhibiting activities, and a pharmaceutical composition comprising the same which can be useful for prevention or treatment of precancerous transformation or cancer.
- -
-
Page/Page column 58; 59
(2015/11/27)
-
- Nucleophilic Fluorination and Radiofluorination via Aziridinium Intermediates: N-Substituent Influence, Unexpected Regioselectivity, and Differences between Fluorine-19 and Fluorine-18
-
The efficient dehydrofluorination and radiofluorination of N,N-disubstituted-β-aminoalcohols through an anchimeric-assisted mechanism was developed. An investigation into the influence of N-substituents on the ring opening of the aziridinium intermediate indicated differences in the isomeric ratio and the yields of fluorinated products obtained from N,N-disubstituted-phenylalaninol. This influence was substantial for 18F-radiofluorination, with yields varying from 0 to 71% at room temperature (RT). Although no significant effects were observed in the fluorine-19 chemistry when the reaction was heated to 90 °C, considerable changes appeared during radiofluorination. In the latter case, the radiochemical yields increased, and degradation of the 2-fluoro-propan-1-amine isomer (b) occurred, leading to a regiospecific reaction in the radiolabeling of [18F]-fluorodeprenyl. This method involving nucleophilic radiofluorination at RT was successfully applied to the radiolabeling of [18F]-2-fluoroethylamines in which the influence of the N-substituent was also observed.
- Médoc, Marie,Sobrio, Franck
-
p. 10086 - 10097
(2015/11/03)
-
- COPOLYMERS FOR STABLE MICELLE FORMULATIONS
-
The present invention relates to the field of polymer chemistry and more particularly to multiblock copolymers and micelles comprising the same. Compositions herein are useful for drug-delivery applications.
- -
-
Paragraph 0342; 0343; 0344
(2014/09/29)
-
- Catalytic reductive dehydration of tertiary amides to enamines under hydrosilylation conditions
-
Tertiary amides are efficiently reduced to their corresponding enamines under hydrosilylation conditions, using a transition-metal-free catalytic protocol based on t-BuOK (5 mol %) and (MeO)3SiH or (EtO) 3SiH as the reducing agent. The enamines were formed with high selectivity in good-to-excellent yields.
- Volkov, Alexey,Tinnis, Fredrik,Adolfsson, Hans
-
p. 680 - 683
(2014/03/21)
-
- Dibenzylamine hydrophobe
-
The present invention relates to a compound characterized by the following formula: wherein each R1 is independently methyl or ethyl; and n 1 to 10. The compound is useful in preparing hydrophobically modified alkylene oxide urethane polymers, which are useful as rheology modifiers for coatings formulations.
- -
-
Paragraph 0018
(2013/11/05)
-
- Mild and efficient capture and functionalisation of CO2 using silver(i) oxide and application to 13C-labelled dialkyl carbonates
-
A high yielding three-component reaction between β-iodo ethylamine derivatives, MeOH and gaseous CO2 at ambient temperatures and pressures is reported using silver(i) oxide. Unfunctionalised alkyl iodides were also found to be effective in this transformation and their optimisation is also described. To highlight the ease and control with which gaseous CO 2 can be captured and functionalised under mild conditions, the reaction was performed using 13C-enriched CO2 to afford specifically 13C-carbonyl-labelled dialkyl carbonates with exquisite control of the isotopic purity in good yields and without the need for specialised equipment.
- Tunbridge, Gemma A.,Baruchello, Riccardo,Caggiano, Lorenzo
-
p. 4613 - 4621
(2013/05/08)
-
- DAST mediated preparation of β-fluoro-α-aminophosphonates
-
Herein, we report a new and convenient method for the synthesis of β-fluoro-α-aminophosphonates starting from naturally occurring l-amino acids. A key step in the synthetic protocol involves nucleophilic fluorination of N,N-dibenzylated-β-amino alcohols with diethylaminosulfur trifluoride (DAST).
- Ka?mierczak, Marcin,Koroniak, Henryk
-
experimental part
p. 23 - 27
(2012/06/30)
-
- POLYMER MICELLES CONTAINING ANTHRACYLINES FOR THE TREATMENT OF CANCER
-
The present invention provides micelles having an anthracycline encapsulated therein, the micelles comprising a multiblock copolymer. The invention further provides methods of preparing and using said micelles, and compositions thereof.
- -
-
Page/Page column 54
(2010/11/17)
-
- Glucosamine conjugates bearing N,N,O-donors: Potential imaging agents utilizing the [M(CO)3]+ core (M = Re, Tc)
-
The design rationale, synthesis and radiolabeling evaluation of four glucosamine conjugated ligands for the [99mTc(CO)3] + core is described. The capability to bind the tricarbonyl core is initially demonstrated using the cold surrogate [Re(CO)3] +. The four compounds are competent chelates in binding [ 99mTc(CO)3]+ as labeling studies show, with yields ranging from 79 to 96% and the resulting complexes showing stability in the presence of competing chelates for 24 h at 37 °C. The rhenium complexes were tested for hexokinase-catalysed phosphorylation, and the technetium complexes were tested for GLUT-1 mediated cell uptake - they showed a small amount of uptake but it was not glucose dependent, suggesting that it was not via the GLUT-1 transporters.
- Bowen, Meryn L.,Lim, Nathaniel C.,Ewart, Charles B.,Misri, Ripen,Ferreira, Cara L.,Haefeli, Urs,Adam, Michael J.,Orvig, Chris
-
experimental part
p. 9216 - 9227
(2010/02/15)
-
- Towards convenient precursors for α-phosphonylated aziridinium ions
-
Mixtures of the respective 2-(N,N-dibenzylamino)-1-chloro- and 1-(N,N-dibenzylamino)-2-chlorophosphonates were obtained after mesylation of dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-methylbutylphosphonate and diethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate with mesyl chloride in the presence of tetraethylammonium chloride. These mixtures are considered as useful precursors to-phosphonylated aziridinium ions.
- Piotrowska, Dorota G.,Wroblewski, Andrzej E.
-
experimental part
p. 998 - 1016
(2009/12/03)
-
- Synthesis and noncovalent protein conjugation of linear-hyperbranched PEG-poly(glycerol) α,ωn-telechelics
-
(Figure Presented) Linear-hyperbranched, heterobifunctional α,ωn telechelic block copolymers consisting of a linear poly(ethylene glycol) (PEG) chain and a hyperbranched polyglycerol (PG) blockhave been prepared in five steps, using a protected amino-functional in itiator. The polyfunctionality ωn (OH groups) can be adjusted by the degree of polymerization (DPn) of the polyglycerol block. Subsequent introduction of a single biotin unit by amidation in α-position permitted noncovalent bioconjugation with avidin.
- Wurm, Frederik,Klos, Johannes,Raeder, Hans Joachim,Frey, Holger
-
supporting information; experimental part
p. 7954 - 7955
(2009/12/03)
-
- Use of a compound having a monogalactosyldiacylglycerol synthase inhibitory activity as herbicide or algaecide, herbicide and algaecide compositions
-
The invention relates to the use of compounds having a monogalactosyldiacylglycerol (MGDG) synthase inhibitory activity as herbicide or algaecide, and to herbicide and algaecide compositions containing at least one of these compounds.
- -
-
Page/Page column 41
(2009/01/20)
-
- Compounds with antiparasitic activity, applications thereof to the treatment of infectious diseases caused by apicomplexans
-
The Invention relates to compounds having an antiparasitic activity, and to their use as a drug, in particular as a drug for the prevention and/or treatment of parasitic diseases caused by apicomplexans. The invention also relates to pharmaceutical compositions containing those compounds.
- -
-
Page/Page column 88
(2009/01/20)
-
- COMPOSITION FOR REPELLING AND DETERRING VERMIN
-
The invention describes essentially a non-therapeutical process for deterring vermin, which is based on the usage of the largely known beta amino-alcohol derivatives of formula (I), as defined herein before. Furthermore, it describes the corresponding vermin-deterring compositions which contain these substances as the active ingredient, compounds of the formula (I) for the preparation of vermin-deterring compositions, and the use of compounds of formula (I) in the defense against vermin. Thus, the invention describes how and in which form the compounds of the formula (I) or their acid addition salts are used to deter vermin from materials, places or warm-blooded animals.
- -
-
Page/Page column 13
(2008/12/05)
-
- Stereoselective synthesis and conformational analysis of unnatural tetrapeptides. Part 2
-
Stereoselective synthesis of unnatural tetrapeptides 20a and 20b, 21a and 21b and 30 and 31, containing two l-valine units and two unnatural α-amino acids (ornithine and modified aspartic acid), has been accomplished starting from the l-valine derived chiral synthon 1. Structural investigations of these non-proteinogenic peptides have been carried out on the acetamido derivatives using 1H NMR, IR spectroscopic techniques and a conformational analysis based on molecular dynamics (MD) and cluster analysis.
- Almiento, Giosue M.,Balducci, Daniele,Bottoni, Andrea,Calvaresi, Matteo,Porzi, Gianni
-
p. 2695 - 2711
(2008/09/17)
-
- Synthesis of radiolabeled sugar metal complexes
-
The invention provides a method for manufacturing or preparing neutral, low molecular weight 99mTc-labeled and 186Re-labeled carbohydrate complexes with an improved radiochemical yield from a simple functionalized sugar, such as glucosamine. In particular the synthesis relies on single ligand transfer (SLT) or double ligand transfer (DLT) reactions for converting a ferrocene compound into a rhenium or technetium tricarbonyl complex. The ferrocene compound may be linked to a sugar through various functional groups including, for example, thio, amino and alcohol functionalities to provide a wide range of radiolabeled sugar complexes that include both water soluble and relatively water insoluble compounds.
- -
-
Page/Page column 7; 24
(2008/06/13)
-
- HETEROBIFUNCTIONAL POLY(ETHYLENE GLYCOL) AND USES THEREOF
-
The present invention provides bifunctional polymers, methods of preparing the same, and intermediates thereto. These compounds are useful in a variety of applications including the PEGylation of biologically active molecules. The invention also provides methods of using said compounds and compositions thereof.
- -
-
Page/Page column 77
(2010/11/08)
-
- Total synthesis of (-)-7-epicylindrospermopsin, a toxic metabolite of the freshwater cyanobacterium Aphanizomenon ovalisporum, and assignment of its absolute configuration
-
(Chemical Equation Presented) The Z and E nitrones 38 and 39 from condensation of aldehyde 20 with hydroxylamine 36 underwent intramolecular dipolar cycloaddition to give the substituted 1-aza-7-oxobicyclo[2.2.1] heptanes 40 and 41 in a ratio of 2:1, respectively. Reductive N-O bond cleavage of 40 followed by carbonylation gave cyclic urea 47 in which inversion of the secondary alcohol was effected via an oxidation-reduction sequence. After conversion of the p-bromobenzyl ether 50 to azide 54, activation of the cyclic urea as its O-methylisourea and reduction of the azide led to spontaneous cyclization to afford the tricyclic nucleus 59 of cylindrospermopsin. Global deprotection, including hydrolysis of the 2,4-dimethyoxypyrimidine appendage to a uracil, and then monosulfation of the resultant diol 60 afforded a substance identical with natural (-)-7-epicylindrospermopsin (1). The asymmetric synthesis of (-)-7-epicylindrospermopsin defines its absolute configuration as 7S,8R,10S,12S,13R,14S.
- White, James D.,Hansen, Joshua D.
-
p. 1963 - 1977
(2007/10/03)
-
- Asymmetric synthesis of L-[4-13C]lysine by alkylation of oxazinone derivative as a chiral glycine equivalent
-
L-[4-13C]Lysine (2) was synthesized from sodium [2- 13C]acetate (3) and Dellaria's oxazinone 1 as a chiral glycine equivalent. Wittig reaction of the glycinal 7 and 13C-labeled phosphonium ylide 5, prepared from sodium [2-13C]acetate (3), gave the α, β-unsaturated ester 8. The ester 8 was converted to the allylic bromide 10. Alkylation of the oxazinone 1 with 10 proceeded with high diastereoselectivity. Ethanolysis, hydrogenation of the double bond with diimide, removal of the chiral auxiliary, and hydrolysis gave L-[4- 13C]lysine (2). Copyright
- Takatori, Kazuhiko,Hayashi, Akira,Kajiwara, Masahiro
-
p. 787 - 795
(2007/10/03)
-
- 3-piperidyl-4-oxoquinazoline derivatives and pharmaceutical compositions comprising the same
-
3-piperidyl-4-oxoquinazoline derivatives are provided, which is represented by the formula (I): wherein R represents an amino group or a cyclic amino group such as dibenzoazepine, each of which is substituted with a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the like, n is an integer of 1 to 3, R3and R4independently represents a hydrogen atom, a lower alkyl group, or the like, or a pharmaceutically acceptable salt thereof. Compounds (I) of the present invention have excellent MTP-inhibitory activity. Thus, these compounds not only inhibit formation of LDL that is a cause of arteriosclerotic diseases but also regulate TG, cholesterol, and lipoproteins such as LDL in the blood and regulate cellular lipids through regulation of MTP activity. They can also be used as a new type of preventive or therapeutic agents for hyperlipemia or arteriosclerotic diseases. Furthermore, they can be used as therapeutic or preventive agents for pancreatitis, obesity, hypercholesterolemia, and hypertriglyceridemia.
- -
-
-
- Stereoselective deprotonation of chiral and achiral 2-aminoalkyl carbamates: Synthesis of optically active β-amino alcohols via 1-oxy- substituted alkyllithium intermediates
-
A facile protocol for the electrophilic C-substitution (methylation, acylation, α-hydroxyalkylation, and carboxylation) of several 2-(N,N- dibenzylamino)alkan-1-ols via the carbamates 10 is reported. The stereochemistry of the lithiation is greatly influenced by the complexing diamine. The substrate-directed selection between the diastereotopic a-pro-R and pro-S protons in the TMEDA-assisted deprotonation is largely shifted towards pro-S-selectivity in the presence of (-)-sparteine (4). Each of both diastereomeric series is readily accessible in several cases.
- Schwerdtfeger, J?rg,Kolczewski, Sabine,Weber, Berthold,Fr?hlich, Roland,Hoppe, Dieter
-
p. 1573 - 1592
(2007/10/03)
-
- Design and synthesis of imidazoline derivatives active on glucose homeostasis in a rat model of type ii diabetes. 2. Syntheses and biological activities of 1,4-dialkyl-, 1,4-dibenzyl, and 1-benzyl-4-alkyl-2-(4',5'- dihydro-1'H-imidazol-2'-yl)piperazines and isosteric analogues of imidazoline
-
Piperazine derivatives have been identified as new antidiabetic compounds. Structure-activity relationship studies in a series of 1-benzyl- 4-alkyl-2-(4',5'-dihydro-1'H-imidazol-2'-yl)piperazines resulted in the identification of 1-methyl-4-(2',4'-dichlorobenzyl)-2-(4',5'-dihydro-1'H- imidazol-2'-yl)piperazine, PMS 812 (S-21663), as a highly potent antidiabetic agent on a rat model of diabetes, mediated by an important increase of insulin secretion independently of α2 adrenoceptor blockage. These studies were extended to find additional compounds in these series with improved properties. In such a way, substitution of both piperazine N atoms was first optimized by using various alkyl, branched or not, and benzyl groups. Second, some modifications of the imidazoline ring and its replacement by isosteric heterocycles were carried out, proceeding from PMS 812, to evaluate their influence on the antidiabetic activity. The importance of the distance between the imidazoline ring and the piperazine skeleton was studied third. Finally, the influence of the N-benzyl moiety was also analyzed compared to a direct N-phenyl substitution. The pharmacological evaluation was performed in vivo using glucose tolerance tests on a rat model of type II diabetes. The most active compounds were 1,4-diisopropyl-2-(4',5'-dihydro-1'H-imidazol-2'- yl)piperazine (41a), PMS 847 (S-22068), and 1,4-diisobutyl-2-(4',5'-dihydro- 1'H-imidazol-2'-yl)piperazine (41b), PMS 889 (S-22575), which strongly improved glucose tolerance without any side event or hypoglycemic effect. More particularly, PMS 847 proved to be as potent after po (100 μmol/kg) as after ip administration and appears as a good candidate for clinical investigations.
- Le Bihan, Ga?lle,Rondu, Frédéric,Pelé-Tounian, Agnès,Wang, Xuan,Lidy, Sandrine,Touboul, Estéra,Lamouri, Aazdine,Dive, Georges,Huet, Jack,Pfeiffer, Bruno,Renard, Pierre,Guardiola-Lema?tre, Béatrice,Manéchez, Dominique,Pénicaud, Luc,Ktorza, Alain,Godfroid, Jean-Jacques
-
p. 1587 - 1603
(2007/10/03)
-
- Enantioselective synthesis of differently protected 1,2-diamines via α-alkylation of dibenzylaminoacetaldehyde SAMP-hydrazone
-
Chiral, unsymmetrically and differently protected 1,2-diamines 4 were prepared in moderate to good overall yields and with high asymmetric inductions (ee = 91-99%) by α-alkylation of N,N-dibenzylaminoacetaldehyde SAMP-hydrazone (S)-2 with subsequent oxidative cleavage to the corresponding α-aminonitriles, reduction to the diamines, and protection of the latter.
- Enders, Dieter,Schiffers, Robert
-
-
- Inhibitory effect of 2-(E-2-alkenoylamino)ethyl alkyl sulfides on gastric ulceration in rats. II. Structure and activity relationships of 2(E-n or Z-n-decenoylamino)ethyl alkyl sulfides
-
The analogues of 2-(E-n or Z-n-decenoylamino)ethyl carbamoylmethyl sulfide, including the modifications of sulfide portion, double bond in decenoyl chain and alkyl sulfide moiety, were synthesized and their inhibitory effects on stress-induced ulceration in rats were compared. Replacing the sulfura atom by methylene group or oxygen atom reduced the effect of potency. Saturation of the double bond in the decenoyl chain tended to reduce the anti-ulcerogenic activity in rats. There was no relationship between the position of double bond in decenoyl chain and the pharmacological activity. On the other hand, compounds with E-configuration showed stronger anti-ulcer activity than the corresponding Z-type of compounds. Among 9 kinds of S substituted alkyl groups for carbamoylmethyl, 2-(E-2-decenoylamino)ethyl 2-cyclohexylethyl sulfide showed the most potent anti-ulcerogenic activity in rats and also showed the lowest acute toxicity in mice.
- Kohda,Iwai,Watanabe,Arakawa,Fukaya,Yokoyama,Kohama,Mimura
-
p. 1546 - 1550
(2007/10/02)
-
- Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs
-
Quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal anti-inflammatory drugs (NSAIDs) are disclosed. These esters and thioesters display the anti--inflammatory profile of the parent NSAIDs with greatly reduced gastrointestinal irritancy, providing a more favorable separation of therapeutic activity and toxicological side effects than the parent NSAIDs.
- -
-
-