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  1. Article ; Online: Psychedelic-like Activity of Norpsilocin Analogues.

    Sherwood, Alexander M / Burkhartzmeyer, Elise K / Williamson, Samuel E / Baumann, Michael H / Glatfelter, Grant C

    ACS chemical neuroscience

    2024  Volume 15, Issue 2, Page(s) 315–327

    Abstract: Primary metabolites of mushroom tryptamines, psilocybin and baeocystin (i.e., psilocin and norpsilocin), exhibit potent agonist activity at the serotonin 2A receptor (5- ... ...

    Abstract Primary metabolites of mushroom tryptamines, psilocybin and baeocystin (i.e., psilocin and norpsilocin), exhibit potent agonist activity at the serotonin 2A receptor (5-HT
    MeSH term(s) Mice ; Animals ; Hallucinogens/chemistry ; Serotonin/metabolism ; Receptors, Serotonin/metabolism ; Brain/metabolism ; Receptor, Serotonin, 5-HT2A/metabolism
    Chemical Substances Hallucinogens ; omega-N-methyl-4-hydroxytryptamine ; Serotonin (333DO1RDJY) ; Receptors, Serotonin ; Receptor, Serotonin, 5-HT2A
    Language English
    Publishing date 2024-01-08
    Publishing country United States
    Document type Journal Article
    ISSN 1948-7193
    ISSN (online) 1948-7193
    DOI 10.1021/acschemneuro.3c00610
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors.

    Sherwood, Alexander M / Burkhartzmeyer, Elise K / Williamson, Samuel E / Faley, Michael T

    ACS omega

    2023  Volume 8, Issue 24, Page(s) 22132–22137

    Abstract: A divergent two-step process has provided access to optically pure enantiomers of MDMA and MDA, clinically relevant phenylisopropylamine entactogens. Target compounds were synthesized from commercially available alanine-derived aziridines. Critical ... ...

    Abstract A divergent two-step process has provided access to optically pure enantiomers of MDMA and MDA, clinically relevant phenylisopropylamine entactogens. Target compounds were synthesized from commercially available alanine-derived aziridines. Critical process parameters were identified, and the reactions were optimized to avoid chromatographic purifications toward gram-scale isolations, providing (
    Language English
    Publishing date 2023-06-06
    Publishing country United States
    Document type Journal Article
    ISSN 2470-1343
    ISSN (online) 2470-1343
    DOI 10.1021/acsomega.3c02358
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: The Kappa Opioid Receptor Agonist 16-Bromo Salvinorin A Has Anti-Cocaine Effects without Significant Effects on Locomotion, Food Reward, Learning and Memory, or Anxiety and Depressive-like Behaviors.

    van de Wetering, Ross / Ewald, Amy / Welsh, Susan / Kornberger, Lindsay / Williamson, Samuel E / McElroy, Bryan D / Butelman, Eduardo R / Prisinzano, Thomas E / Kivell, Bronwyn M

    Molecules (Basel, Switzerland)

    2023  Volume 28, Issue 12

    Abstract: Kappa opioid receptor (KOR) agonists have preclinical antipsychostimulant effects; however, adverse side effects have limited their therapeutic development. In this preclinical study, conducted in Sprague Dawley rats, B6-SJL mice, and non-human primates ( ...

    Abstract Kappa opioid receptor (KOR) agonists have preclinical antipsychostimulant effects; however, adverse side effects have limited their therapeutic development. In this preclinical study, conducted in Sprague Dawley rats, B6-SJL mice, and non-human primates (NHPs), we evaluated the G-protein-biased analogue of salvinorin A (SalA), 16-bromo salvinorin A (16-BrSalA), for its anticocaine effects, side effects, and activation of cellular signaling pathways. 16-BrSalA dose-dependently decreased the cocaine-primed reinstatement of drug-seeking behavior in a KOR-dependent manner. It also decreased cocaine-induced hyperactivity, but had no effect on responding for cocaine on a progressive ratio schedule. Compared to SalA, 16-BrSalA had an improved side effect profile, with no significant effects in the elevated plus maze, light-dark test, forced swim test, sucrose self-administration, or novel object recognition; however, it did exhibit conditioned aversive effects. 16-BrSalA increased dopamine transporter (DAT) activity in HEK-293 cells coexpressing DAT and KOR, as well as in rat nucleus accumbens and dorsal striatal tissue. 16-BrSalA also increased the early phase activation of extracellular-signal-regulated kinases 1 and 2, as well as p38 in a KOR-dependent manner. In NHPs, 16-BrSalA caused dose-dependent increases in the neuroendocrine biomarker prolactin, similar to other KOR agonists, at doses without robust sedative effects. These findings highlight that G-protein-biased structural analogues of SalA can have improved pharmacokinetic profiles and fewer side effects while maintaining their anticocaine effects.
    MeSH term(s) Mice ; Rats ; Humans ; Animals ; Cocaine/pharmacology ; Receptors, Opioid, kappa/metabolism ; Rats, Sprague-Dawley ; HEK293 Cells ; Anxiety/drug therapy ; Reward ; Locomotion
    Chemical Substances Cocaine (I5Y540LHVR) ; salvinorin A (T56W91NG6J) ; Receptors, Opioid, kappa
    Language English
    Publishing date 2023-06-19
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules28124848
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.MO 81: Show issues

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  4. Article: Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

    Sherwood, Alexander M / Williamson, Samuel E / Johnson, Stephanie N / Yilmaz, Anil / Day, Victor W / Prisinzano, Thomas E

    Journal of organic chemistry. 2018 Jan. 19, v. 83, no. 2

    2018  

    Abstract: A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then ... ...

    Abstract A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (−)-aspinolide A and (−)-5-epi-aspinolide A utilizing a catalytic Nozaki–Hiyama–Kishi reaction to close the macrolide in the final step in 65–84% yields.
    Keywords aldehydes ; chemical reactions ; chemical structure ; epoxides ; fungi ; macrolides ; organic chemistry ; protocols ; regioselectivity ; stereoselective synthesis
    Language English
    Dates of publication 2018-0119
    Size p. 980-992.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.7b02324
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

    Z 4' 49/42: Show issues
    Z 7.1: Show issues

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  5. Article: Modular Approach to pseudo-Neoclerodanes as Designer κ-Opioid Ligands

    Sherwood, Alexander M / Williamson Samuel E / Crowley Rachel S / Abbott Logan M / Day Victor W / Prisinzano Thomas E

    Organic letters. 2017 Oct. 06, v. 19, no. 19

    2017  

    Abstract: Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of ... ...

    Abstract Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of functionality about the target molecule to provide access to molecular features on salvinorin A otherwise unattainable by semisynthesis. Using this approach, a potent pseudo-neoclerodane κ-opioid receptor ligand (2) has been realized.
    Keywords chemical reactions ; chemical structure ; ligands ; organic compounds
    Language English
    Dates of publication 2017-1006
    Size p. 5414-5417.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021%2Facs.orglett.7b02684
    Database NAL-Catalogue (AGRICOLA)

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  6. Article ; Online: Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives.

    Sherwood, Alexander M / Williamson, Samuel E / Johnson, Stephanie N / Yilmaz, Anil / Day, Victor W / Prisinzano, Thomas E

    The Journal of organic chemistry

    2018  Volume 83, Issue 2, Page(s) 980–992

    Abstract: A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then ... ...

    Abstract A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.
    MeSH term(s) Aldehydes/chemistry ; Butanols/chemical synthesis ; Butanols/chemistry ; Epoxy Compounds/chemistry ; Lactones/chemical synthesis ; Lactones/chemistry ; Macrocyclic Compounds/chemical synthesis ; Macrocyclic Compounds/chemistry ; Molecular Structure ; Stereoisomerism
    Chemical Substances Aldehydes ; Butanols ; Epoxy Compounds ; Lactones ; Macrocyclic Compounds ; aspinolide B (188605-15-4)
    Language English
    Publishing date 2018-01-08
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S.
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.7b02324
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  7. Article ; Online: Modular Approach to pseudo-Neoclerodanes as Designer κ-Opioid Ligands.

    Sherwood, Alexander M / Williamson, Samuel E / Crowley, Rachel S / Abbott, Logan M / Day, Victor W / Prisinzano, Thomas E

    Organic letters

    2017  Volume 19, Issue 19, Page(s) 5414–5417

    Abstract: Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of ... ...

    Abstract Informed by previous semisynthetic work on salvinorin A, a modular total synthesis has been developed capable of producing novel compounds targeting the κ-opioid receptor. The strategy has permitted the deliberate simplification and introduction of functionality about the target molecule to provide access to molecular features on salvinorin A otherwise unattainable by semisynthesis. Using this approach, a potent pseudo-neoclerodane κ-opioid receptor ligand (2) has been realized.
    MeSH term(s) Diterpenes/chemistry ; Diterpenes, Clerodane ; Ligands ; Molecular Structure ; Receptors, Opioid, kappa
    Chemical Substances Diterpenes ; Diterpenes, Clerodane ; Ligands ; Receptors, Opioid, kappa ; neoclerodane
    Language English
    Publishing date 2017-09-14
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, U.S. Gov't, Non-P.H.S.
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.7b02684
    Database MEDical Literature Analysis and Retrieval System OnLINE

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