Epinephrine and Related Compounds: Influence of Structure on Physiological Activity.

Hartung, W.

doi:10.1021/cr60034a002

Cited by 47 publications

(13 citation statements)

References 51 publications

(75 reference statements)

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“…It has been shown that tumor necrosis factor receptor II (TNFRII) is increased by epinephrine treatment in monocytes [28], and the level of TNFR expression on the cell surface affects the level of HIV-1 reactivation by TNFα treatment [29]. Since epinephrine and ephedrine share an identical skeleton of β -phenylethylamine and are similar in overall structure [30], we hypothesized that ephedrine treatment might elevate TNFR expression and raise TNFα sensitivity, resulting in an enhancement of HIV-1 reactivation by combination treatment with TNFα. TNFα is a ligand of TNFRI and TNFRII [31].…”

Section: Resultsmentioning

confidence: 99%

Ephedrine enhances HIV-1 reactivation from latency through elevating tumor necrosis factor receptor II (TNFRII) expression

Panaampon

Kudo

Kariya

et al. 2019

Heliyon

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HIV-1 persists during antiretroviral therapy (ART) due to long-lived and proliferating latently-infected host cells, with the outcome being an incomplete cure. The latently-infected cells, or reservoir cells, are transcriptionally absent and invisible to the immune response. Elimination of latency is one strategy in activating virus production, making it visible to immune clearance. We previously showed that Ephedrae herba reactivated HIV-1 from latency. In this study, we used ephedrine, a major component of Ephedra herba, to reactivate HIV-1 from latency. The results showed that ephedrine enhances HIV-1 reactivation in the presence of TNFα. Combination treatment demonstrates a synergistic effect of HIV-1 reactivation compared to TNFα alone. Ephedrine treatment shows a higher TNFRII expression level, which is related to increased HIV-1 reactivation. However, the mechanism of ephedrine in HIV-1 reactivation is still unclear, and may be related to TNFRII receptor expression. Our results indicate that ephedrine enhances HIV-1 reactivation from latency in combination with TNFα treatment. This new reagent could be a promising latency reversal agent (LRA).

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Section: Resultsmentioning

confidence: 99%

Ephedrine enhances HIV-1 reactivation from latency through elevating tumor necrosis factor receptor II (TNFRII) expression

Panaampon

Kudo

Kariya

et al. 2019

Heliyon

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“…Their synthetic importance can be seen in the Tcfeneau-Demjanov and related deaminative semipinacol rearrangements [ 11, and their biological relevance in the structures of adrenalin and related mediators of the sympathetic nervous system [2] [ 3 ] . All of the main synthetic routes to this functional class possess significant limitations to their use [3], particularly in terms of the attainable degree of regioselectivity.…”

Section: Discussionmentioning

confidence: 99%

Improved Nitroaldol Reactions and Reductive Routes to Vicinal Aminoalcohols

Colvin

Beck

Seebàch

1981

Helvetica Chimica Acta

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Dedicated to Prof. Vludirnir Prebg on the occasion of his 75th birthday (17.VII.81) SummaryRegioselective and flexible procedures are described for the preparation of a variety of protected vicinal nitroalcohols 1, 3 and 5 (see Scheme 5), as is an efficient method for their reduction to the corresponding vicinal aminoalcohols 2, 4 and 6. approaches regiospecificity only in highly biased cases. Similarly, the success of the methodssuch as a-halogenation or a-nitrosation of ketones depends upon the degree of regioselectivity attained in the initial a-functionalization [3]. Hydride reduction of free or protected cyanohydrins [5] is of considerable utility, but only in those cases where C1-homologation of the carbonyl substrate is desired.An apparently attractive route to vicinal aminoalcohols requires reduction of the corresponding vicinal nitroalcohols. These latter compounds are accessible by the Henry-161, or nitroaldol reaction, a regioselective method for the coupling of a carbonyl and a nitroalkane component leading to the vicinal relationship between the 0-and N-substituents (Scheme I ) . Such a procedure has been used only infrequently, partly due to the often low yields [7] obtained (except in intramolecular cases and those reactions involving nitromethane itself), and to retro-

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“…As a general rule, however, it is reported that N-methylation reduces the activity (48). (97) CaHs-CHz-CHz-NHCHa '/3SO epinephrine (97) CaHs-AH-CHz-NHz Dialkylation, or conversion into a tertiary amine, decreases the pressor activity, and the larger the alkyl group, the greater the decrease (40). Usually, also, this decrease in activity is accompanied by a simultaneous increase in toxicity.…”

Section: Eppect Op N-alkylationmentioning

confidence: 99%

Beta-Phenethylamine Derivatives

Hartung¹

1945

Ind. Eng. Chem.

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8 -the compounds derived structurally from p-phenethylamine form an attractive series for the pharmacologist and the pharmaceutical chemist. The structure may be modified within wide limits without destroying the characteristic ability eo raise the blood pressure of an experimental animal. It is now possible to ascribe, with considerable reliance, a constant qualitative or quantitative pharmacodynamic modification to the presence of certain substituents i n given positions of the parent skeleton. The effect of two or more substituents, appropriately placed, may prove additive. The chemical structure, including the phenomena of isosterism and optical isomerism, may be correlated with pharmacological properties, especially pressor effects. The therapeutic usefulness of some members of this series is based o n properties other than their ability to cause an elevation in blood pressure. In the light of information now available, the riddle of Abel's "benzoylepinephrine", which showed to a high degree the quantitative potency of pure epinephrine, becomes all the more enigmatic.

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Epinephrine and Related Compounds: Influence of Structure on Physiological Activity.

Cited by 47 publications

References 51 publications

Ephedrine enhances HIV-1 reactivation from latency through elevating tumor necrosis factor receptor II (TNFRII) expression

Ephedrine enhances HIV-1 reactivation from latency through elevating tumor necrosis factor receptor II (TNFRII) expression

Improved Nitroaldol Reactions and Reductive Routes to Vicinal Aminoalcohols

Beta-Phenethylamine Derivatives

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