Zur Darstellung von Derivaten des Nicotinsäureamids

Lettré, Hans; Haede, Werner; Ruhbaum, Eva

doi:10.1002/jlac.19535790207

Cited by 47 publications

(11 citation statements)

References 28 publications

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“…The aqueous phase was then concentrated in vacuo to 5 ml, and applied to a column of cation-exchange resin AG5OWX8 (H+ form) which was rinsed with 500 ml of water then eluted with a gradient of 0 -0. . To a solution of 2.26 g (6.9 mmol) of 3-(aminocarbonyl)-l-(2,4-dinitropheny1)pyridinium chloride VI [6] in 20 ml methanol was added a solution of (5.3 mmol) of D-1-amino-1-deoxy-ribitol [7] in 5 ml methanol. The reaction mixture was magnetically stirred for 48 h at room temperature, the red color at the beginning becoming progressively yellow.…”

Section: Synthesis Of 3-(aminocarbony1)-1-(3-cis-hydroxymethyl Cyclopmentioning

confidence: 99%

Activity of NMN⁺, nicotinamide ribose and analogs in alcohol oxidation promoted by horse‐liver alcohol dehydrogenase

Sicsic¹,

Durand²,

Langrené³

et al. 1986

European Journal of Biochemistry

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Kinetic constants of horse-liver alcohol-dehydrogenase-mediated oxidation of alcohol by nicotinamide mononucleotide and nicotinamide ribose were determined and the role of different adenine moieties complementing the reaction mixtures was investigated. Five nicotinamide ribose analogs were synthesized and their activities as NAD' inhibitors and as cofactors in this dehydrogenase-mediated oxidation of alcohol were assayed. In the light of these results, structural requirements of the pyridine ribofuranosyl part of the NAD' are discussed.In a recent work, we have shown that the enzymatic activity of horse-liver alcohol dehydrogenase (HLADH), an NAD' -requiring enzyme, was partly retained when NMN+ or the nicotinamide ribose (NR') were used as cofactors. Moreover, the efficiencies of these NAD' fragments were strongly improved when the medium was supplemented with adenosine and AMP respectively [I].Many NAD + analogs [2] have been synthesized with, in particular, the nicotinamide-linked ribofuranosyl residue substituted by linear alkyl groups and assayed as cofactors. Only the analog with the butyl group was found to be slightly active, showing the importance of the nicotinamide-linked ri bofuranosyl.We describe in the present work the synthesis of four N R + analogs I -IV, where a cyclopentane diversely substituted is attached to the nicotinamide moiety, and one nicotinamide derivative V, where the nitrogen atom is substituted by a C 5 chain possessing four hydroxyl groups. We also describe the abilities of these derivatives to function as cofactors with HLADH and, in order tentatively to elucidate how adenosine and AMP activate the functional fragments, we present some kinetic studies of the enzymatic reactions. MATERIALS AND METHODSNMN' and NR' were prepared and purified according to [I] and [3] respectively. HLADH was from Sigma; NAD', ADP, AMP and adenosine were from Fluka.The enzyme kinetics were carried out in a 1-ml ultraviolet

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Section: Synthesis Of 3-(aminocarbony1)-1-(3-cis-hydroxymethyl Cyclopmentioning

confidence: 99%

Activity of NMN⁺, nicotinamide ribose and analogs in alcohol oxidation promoted by horse‐liver alcohol dehydrogenase

Sicsic¹,

Durand²,

Langrené³

et al. 1986

European Journal of Biochemistry

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“…The insolubility of the protected intermediates 11, 14, 17 and 31 in methanol caused difficulties, but hydrogenation in acetic acid was successful. The quaternary pyridinium-3-amide (Nys + ) derivatives were formed via the Zincke reaction (Zincke 1903;Lettré et al 1953;Atkinson et al 1965;Génisson et al 1992;Chen et al 1998). The obtained polyamine compounds were converted into poly Nys + 21, 22, 23 and 33 by treatment with excess N-(2,4-dinitrophenyl)-pyridinium chloride in good yields (60-85%).…”

Section: Resultsmentioning

confidence: 99%

Novel, cell-penetrating molecular transporters with flexible backbones and permanently charged side-chains

Bodor

Toth‐Sarudy²,

Holm

et al. 2007

Journal of Pharmacy and Pharmacology

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Various cell-penetrating peptides have been discovered recently that can translocate across plasma membranes and can even carry large cargo molecules into the cells. Because under physiological conditions most of these peptides carry considerable positive charges due to the presence of basic amino acids such as arginine, we decided to investigate whether molecular transporters composed of permanently charged side-chains also possess such cell penetrating ability. Arginine-rich oligomers that have a backbone with increased flexibility due to incorporation of non-alpha-amino acids (epsilon-aminocaproic acid) have been found to be effective molecular transporters. Here, we report the preparation of analogue structures by replacing the arginine residues with the quaternary form of a novel redox amino acid (Nys(+)) that contain a trigonelline moiety; it has already been shown possible to replace the original basic amino acid side-chain of neuropeptides without significant activity-loss due to the sufficiently close steric and electronic analogy between the new Nys(+) and the original side-chains (in their protonated form, e.g., Arg(+), Lys(+)). A nonamer analogue showed transporter activity resulting in increased cellular uptake in human carcinoma (HeLa) cells.

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“…In CDC13 one diastereomer exhibited the ethano methine proton resonance at 5.55 ppm while the second diastereomer's methine resonance appeared at 5.35 ppm; the respective melting points of the compounds are 199-202 °C and 140-143 °C. Employing the arguments advanced by Huang et al, 16,17 the higher melting diastereomer is tentatively assigned the meso configuration. 18 If polar interactions were to govern the conformations of meso-5, it would be expected that the preferred conformation of meso-5 would be 5a (Figure 1); there exists in this conformation two pairs of attractive interactions (pentafluorophenyl-p-methoxyphenyl), while in conformers 5b and 5c two pairs of repulsive interactions exist with only a single attractive interaction.…”

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confidence: 81%

Attractive nonbonded interactions. The solution conformation of N-(1-phenyl-2-propyl)nicotinamide chloride

EL-TORKI¹,

Jacobus²

1985

J. Org. Chem.

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PFP PM 2 H H a M E S O -5 Figure 1. Conformations of 1,2-bis(pentafluorophenyl)-l,2-bis-(p-methoxypheny1)ethane. PMP = p-methoxyphenyl; PFP = perfluorophenyl.were prepared and analyzed.(Pentafluorophenyl)(p-methoxypheny1)methanol was coupled in the presence of chromium(I1) chloride to yield an equimolar (by NMR analysis) mixture of the diastereomeric 1,2-bis(p-methoxyphenyl)-1,2-bis(pentafluoro-pheny1)ethanes (meso-and dZ-5).15 The separation of the diastereomers was readily accomplished by successive crystallizations. In CDC1, one diastereomer exhibited the ethano methine proton resonance at 5.55 ppm while the second diastereomer's methine resonance appeared at 5.35 ppm; the respective melting points of the compounds are 199-202 "C and 140-143 OC. Employing the arguments advanced by Huang et al.,16J7 the higher melting diastereomer is tentatively assigned the meso configuration.18If polar interactions were to govern the conformations of meso-5, it would be expected that the preferred conformation of meso-5 would be 5a ( Figure 1); there exists in this conformation two pairs of attractive interactions (pentafluorophenyl-p-methoxyphenyl), while in conformers 5b and 5c two pairs of repulsive interactions exist with only a single attractive interaction. For dl-5, conformer 5a exhibits two pairs of repulsive interactions while both 5b and 5c exhibit two attractive and one repulsive interaction each. Assuming that the repulsive interaction between pentafluorophenyl groups would exceed that of p-methoxyphenyl groups, the preferred conformer of dl-5 would be 5c.Nuclear magnetic resonance analysis of the two diastereomers was conducted at 300 MHz employing the 13C satellite method., In CCll solution the 5.55 ppm diastereomer (meso) has 3&H = 13.25 f 0.15 Hz while the 5.35-ppm diastereomer (dl) has ,JHH = 12.65 f 0.05 Hz.It is clear that both diastereomers exist predominantly in the H-H anti conformation and that the anticipated ring-ring interactions do not, in this case, overcome the repulsive steric interactions encountered in H-H gauche conformations. It should be noted, however, that the coupling constants observed are in agreement with the tentative configurational assignments, i.e., the meso diastereomer should prefer the H-H anti conformation to a greater extent than the dl diastereomer with a resultant greater vicinal coupling constant. Experimental Section(Pentafluorophenyl)(p-methoxypheny1)methanol was prepared by the addition of 5.44 g (0.04 mol) of p-anisaldehyde (15) The coupling reaction is analogous to one reported previously by Finnoccharo et al. (Finnacchario, P.; Gust, G.; Hounshell, W. D.; Hummel, J.; Maravigna, P.; Mislow, K. (18) See, however, the caveat and exception listed in ref 8. 0022-3263/85/1950-1314$01.50/0to the Grignard reagent prepared from 12.35 g (0.05 mol) of bromopentafluorobenzene and 1.22 g (0.05 mol) of Mg turnings in 70 mL of anhydrous ether. Stirring was continued for 2 h after the addition was completed. The reaction mixture was cooled in an ice bath and the reaction was quenched...

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Zur Darstellung von Derivaten des Nicotinsäureamids

Cited by 47 publications

References 28 publications

Activity of NMN⁺, nicotinamide ribose and analogs in alcohol oxidation promoted by horse‐liver alcohol dehydrogenase

Activity of NMN⁺, nicotinamide ribose and analogs in alcohol oxidation promoted by horse‐liver alcohol dehydrogenase

Novel, cell-penetrating molecular transporters with flexible backbones and permanently charged side-chains

Attractive nonbonded interactions. The solution conformation of N-(1-phenyl-2-propyl)nicotinamide chloride

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Zur Darstellung von Derivaten des Nicotinsäureamids

Cited by 47 publications

References 28 publications

Activity of NMN+, nicotinamide ribose and analogs in alcohol oxidation promoted by horse‐liver alcohol dehydrogenase

Activity of NMN+, nicotinamide ribose and analogs in alcohol oxidation promoted by horse‐liver alcohol dehydrogenase

Novel, cell-penetrating molecular transporters with flexible backbones and permanently charged side-chains

Attractive nonbonded interactions. The solution conformation of N-(1-phenyl-2-propyl)nicotinamide chloride

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Activity of NMN⁺, nicotinamide ribose and analogs in alcohol oxidation promoted by horse‐liver alcohol dehydrogenase

Activity of NMN⁺, nicotinamide ribose and analogs in alcohol oxidation promoted by horse‐liver alcohol dehydrogenase