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Michele C Connelly - One of the best experts on this subject based on the ideXlab platform.

  • synthesis and evaluation of methylsulfonylnitrobenzamides msnbas as inhibitors of the thyroid hormone receptor coactivator interaction
    Bioorganic & Medicinal Chemistry Letters, 2013
    Co-Authors: Jong Yeon Hwang, Ramy R Attia, Angela K Carrillo, Michele C Connelly
    Abstract:

    We previously identified the methylsulfonylnitrobenzoates (MSNBs) that block the interaction of the thyroid hormone receptor with its obligate transcriptional coactivators and prevent thyroid hormone signaling. As part of our lead optimization work we demonstrated that sulfonylnitrophenylthiazoles (SNPTs), which replace the Ester Linkage of MSNBs with a thiazole, also inhibited coactivator binding to TR. Here we report that replacement of the Ester with an amide (methylsulfonylnitrobenzamides, MSNBA) also provides active TR antagonists.

  • synthesis and evaluation of sulfonylnitrophenylthiazoles snpts as thyroid hormone receptor coactivator interaction inhibitors
    Journal of Medicinal Chemistry, 2012
    Co-Authors: Jong Yeon Hwang, Ramy R Attia, Lei Yang, Andrew S Lemoff, Cynthia Jeffries, Michele C Connelly
    Abstract:

    We previously identified a series of methylsulfonylnitrobenzoates (MSNBs) that block the interaction of the thyroid hormone receptor with its coactivators. MSNBs inhibit coactivator binding through irreversible modification of cysteine 298 of the thyroid hormone receptor (TR). Although MSNBs have better pharmacological features than our first generation inhibitors (β-aminoketones), they contain a potentially unstable Ester Linkage. Here we report the bioisosteric replacement of the Ester Linkage with a thiazole moiety, yielding sulfonylnitrophenylthiazoles (SNPTs). An array of SNPTs representing optimal side chains from the MSNB series was constructed using parallel chemistry and evaluated to test their antagonism of the TR-coactivator interaction. Selected active compounds were evaluated in secondary confirmatory assays including regulation of thyroid response element driven transcription in reporter constructs and native genes. In addition the selected SNPTs were shown to be selective for TR relative to...

Jong Yeon Hwang - One of the best experts on this subject based on the ideXlab platform.

  • synthesis and evaluation of methylsulfonylnitrobenzamides msnbas as inhibitors of the thyroid hormone receptor coactivator interaction
    Bioorganic & Medicinal Chemistry Letters, 2013
    Co-Authors: Jong Yeon Hwang, Ramy R Attia, Angela K Carrillo, Michele C Connelly
    Abstract:

    We previously identified the methylsulfonylnitrobenzoates (MSNBs) that block the interaction of the thyroid hormone receptor with its obligate transcriptional coactivators and prevent thyroid hormone signaling. As part of our lead optimization work we demonstrated that sulfonylnitrophenylthiazoles (SNPTs), which replace the Ester Linkage of MSNBs with a thiazole, also inhibited coactivator binding to TR. Here we report that replacement of the Ester with an amide (methylsulfonylnitrobenzamides, MSNBA) also provides active TR antagonists.

  • synthesis and evaluation of sulfonylnitrophenylthiazoles snpts as thyroid hormone receptor coactivator interaction inhibitors
    Journal of Medicinal Chemistry, 2012
    Co-Authors: Jong Yeon Hwang, Ramy R Attia, Lei Yang, Andrew S Lemoff, Cynthia Jeffries, Michele C Connelly
    Abstract:

    We previously identified a series of methylsulfonylnitrobenzoates (MSNBs) that block the interaction of the thyroid hormone receptor with its coactivators. MSNBs inhibit coactivator binding through irreversible modification of cysteine 298 of the thyroid hormone receptor (TR). Although MSNBs have better pharmacological features than our first generation inhibitors (β-aminoketones), they contain a potentially unstable Ester Linkage. Here we report the bioisosteric replacement of the Ester Linkage with a thiazole moiety, yielding sulfonylnitrophenylthiazoles (SNPTs). An array of SNPTs representing optimal side chains from the MSNB series was constructed using parallel chemistry and evaluated to test their antagonism of the TR-coactivator interaction. Selected active compounds were evaluated in secondary confirmatory assays including regulation of thyroid response element driven transcription in reporter constructs and native genes. In addition the selected SNPTs were shown to be selective for TR relative to...

Ramy R Attia - One of the best experts on this subject based on the ideXlab platform.

  • synthesis and evaluation of methylsulfonylnitrobenzamides msnbas as inhibitors of the thyroid hormone receptor coactivator interaction
    Bioorganic & Medicinal Chemistry Letters, 2013
    Co-Authors: Jong Yeon Hwang, Ramy R Attia, Angela K Carrillo, Michele C Connelly
    Abstract:

    We previously identified the methylsulfonylnitrobenzoates (MSNBs) that block the interaction of the thyroid hormone receptor with its obligate transcriptional coactivators and prevent thyroid hormone signaling. As part of our lead optimization work we demonstrated that sulfonylnitrophenylthiazoles (SNPTs), which replace the Ester Linkage of MSNBs with a thiazole, also inhibited coactivator binding to TR. Here we report that replacement of the Ester with an amide (methylsulfonylnitrobenzamides, MSNBA) also provides active TR antagonists.

  • synthesis and evaluation of sulfonylnitrophenylthiazoles snpts as thyroid hormone receptor coactivator interaction inhibitors
    Journal of Medicinal Chemistry, 2012
    Co-Authors: Jong Yeon Hwang, Ramy R Attia, Lei Yang, Andrew S Lemoff, Cynthia Jeffries, Michele C Connelly
    Abstract:

    We previously identified a series of methylsulfonylnitrobenzoates (MSNBs) that block the interaction of the thyroid hormone receptor with its coactivators. MSNBs inhibit coactivator binding through irreversible modification of cysteine 298 of the thyroid hormone receptor (TR). Although MSNBs have better pharmacological features than our first generation inhibitors (β-aminoketones), they contain a potentially unstable Ester Linkage. Here we report the bioisosteric replacement of the Ester Linkage with a thiazole moiety, yielding sulfonylnitrophenylthiazoles (SNPTs). An array of SNPTs representing optimal side chains from the MSNB series was constructed using parallel chemistry and evaluated to test their antagonism of the TR-coactivator interaction. Selected active compounds were evaluated in secondary confirmatory assays including regulation of thyroid response element driven transcription in reporter constructs and native genes. In addition the selected SNPTs were shown to be selective for TR relative to...

Lidia Feliu - One of the best experts on this subject based on the ideXlab platform.

  • Solid-Phase Synthesis of Cyclic Depsipeptides Containing a Tyrosine Phenyl Ester Bond
    Organic Letters, 2016
    Co-Authors: Cristina Rosés, Cristina Camó, Kristy Vogels, Marta Planas, Lidia Feliu
    Abstract:

    The first solid-phase strategy for the synthesis of cyclic depsipeptides containing a phenyl Ester Linkage in their structure is described. The key steps of the synthesis were the formation of the phenyl Ester bond and the on-resin head-to-side-chain cyclization. The amino acid configuration significantly influenced the formation and the stability of the cyclic depsipeptides. The presence of a l-Tyr1 and a d-Tyr7 led to the most stable sequences.

Ronald Micura - One of the best experts on this subject based on the ideXlab platform.