The Experts below are selected from a list of 360 Experts worldwide ranked by ideXlab platform
Jeffrey W Bode - One of the best experts on this subject based on the ideXlab platform.
-
iridium catalyzed synthesis of saturated n heterocycles from aldehydes and snap reagents with continuous flow photochemistry
Organic Letters, 2018Co-Authors: Chalupat Jindakun, Shengying Hsieh, Jeffrey W BodeAbstract:Commercially available tin amine protocol (SnAP) reagents provide a simple approach to the synthesis of a wide variety of saturated N-heterocycles from aldehydes. In this report, we disclose that the copper(II) promoter and hexafluoroisopropanol can be replaced by photocatalytic conditions using Ir[dF(CF3)ppy]2(dtbbpy)PF6 in CH3CN. Continuous flow photochemical conditions provide a clean, scalable approach to valuable products including morpholines, piperazines, Thiomorpholines, diazepanes, and oxazepanes from aldehyde starting materials.
-
Iridium-catalyzed Synthesis of Saturated N‑Heterocycles from Aldehydes and SnAP Reagents with Continuous Flow Photochemistry
2018Co-Authors: Chalupat Jindakun, Shengying Hsieh, Jeffrey W BodeAbstract:Commercially available tin amine protocol (SnAP) reagents provide a simple approach to the synthesis of a wide variety of saturated N-heterocycles from aldehydes. In this report, we disclose that the copper(II) promoter and hexafluoroisopropanol can be replaced by photocatalytic conditions using Ir[dF(CF3)ppy]2(dtbbpy)PF6 in CH3CN. Continuous flow photochemical conditions provide a clean, scalable approach to valuable products including morpholines, piperazines, Thiomorpholines, diazepanes, and oxazepanes from aldehyde starting materials
-
continuous flow synthesis of morpholines and oxazepanes with silicon amine protocol slap reagents and lewis acid facilitated photoredox catalysis
Organic Letters, 2017Co-Authors: Moritz K. Jackl, Luca Legnani, Bill Morandi, Jeffrey W BodeAbstract:Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, Thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-catalyzed aminoetherification of olefins.
-
Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis
2017Co-Authors: Moritz K. Jackl, Luca Legnani, Bill Morandi, Jeffrey W BodeAbstract:Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, Thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-catalyzed aminoetherification of olefins
-
Lewis Acid Induced Toggle from Ir(II) to Ir(IV) Pathways in Photocatalytic Reactions: Synthesis of Thiomorpholines and Thiazepanes from Aldehydes and SLAP Reagents
2016Co-Authors: Shengying Hsieh, Jeffrey W BodeAbstract:Redox neutral photocatalytic transformations often require careful pairing of the substrates and photoredox catalysts in order to achieve a catalytic cycle. This can limit the range of viable transformations, as we recently observed in attempting to extend the scope of the photocatalytic synthesis of N-heterocycles using silicon amine protocol (SLAP) reagents to include starting materials that require higher oxidation potentials. We now report that the inclusion of Lewis acids in photocatalytic reactions of organosilanes allows access to a distinct reaction pathway featuring an Ir(III)*/Ir(IV) couple instead of the previously employed Ir(III)*/Ir(II) pathway, enabling the transformation of aromatic and aliphatic aldehydes to Thiomorpholines and thiazepanes. The role of the Lewis acid in accepting an electroneither directly or via coordination to an iminecan be extended to other classes of photocatalysts and transformations, including oxidative cyclizations. The combination of light induced reactions and Lewis acids therefore promises access to new pathways and transformations that are not viable using the photocatalysts alone
Adam Mccluskey - One of the best experts on this subject based on the ideXlab platform.
-
heterocyclic substituted cantharidin and norcantharidin analogues synthesis protein phosphatase 1 and 2a inhibition and anti cancer activity
Bioorganic & Medicinal Chemistry Letters, 2007Co-Authors: Timothy A Hill, Scott G Stewart, Benjamin Sauer, Jayne Gilbert, Stephen P Ackland, Jennette A Sakoff, Adam MccluskeyAbstract:Norcantharidin (3) is a potent PP1 (IC(50)=9.0+/-1.4 microM) and PP2A (IC(50)=3.0+/-0.4 microM) inhibitor with 3-fold PP2A selectivity and induces growth inhibition (GI(50) approximately 45 microM) across a range of human cancer cell lines including those of colorectal (HT29, SW480), breast (MCF-7), ovarian (A2780), lung (H460), skin (A431), prostate (DU145), neuroblastoma (BE2-C), and glioblastoma (SJ-G2) origin. Until now limited modifications to the parent compound have been tolerated. Surprisingly, simple heterocyclic half-acid norcantharidin analogues are more active than the original lead compound, with the morphilino-substituted (9) being a more potent (IC(50)=2.8+/-0.10 microM) and selective (4.6-fold) PP2A inhibitor with greater in vitro cytotoxicity (GI(50) approximately 9.6 microM) relative to norcantharidin. The analogous thiomorpholine-substituted (10) displays increased PP1 inhibition (IC(50)=3.2+/-0 microM) and reduced PP2A inhibition (IC(50)=5.1+/-0.41 microM), to norcantharidin. Synthesis of the analogous cantharidin analogue (19) with incorporation of the amine nitrogen into the heterocycle further increases PP1 (IC(50)=5.9+/-2.2 microM) and PP2A (IC(50)=0.79+/-0.1 microM) inhibition and cell cytotoxicity (GI(50) approximately 3.3 microM). These analogues represent the most potent cantharidin analogues thus reported.
-
heterocyclic substituted cantharidin and norcantharidin analogues synthesis protein phosphatase 1 and 2a inhibition and anti cancer activity
Bioorganic & Medicinal Chemistry Letters, 2007Co-Authors: Timothy A Hill, Scott G Stewart, Benjamin Sauer, Jayne Gilbert, Stephen P Ackland, Jennette A Sakoff, Adam MccluskeyAbstract:Norcantharidin (3) is a potent PP1 (IC50 = 9.0 +/- 1.4 mu M) and PP2A (IC50 = 3.0 +/- 0.4 mu M) inhibitor with 3-fold PP2A selectivity and induces growth inhibition (GI(50) similar to 45 mu M) across a range of human cancer cell lines including those of colorectal (HT29, SW480), breast (MCF-7), ovarian (A2780), lung (H460), skin (A431), prostate (DU145), neuroblastoma (BE2-C), and glioblastoma (SJ-G2) origin. Until now limited modifications to the parent compound have been tolerated. Surprisingly, simple heterocyclic half-acid norcantharidin analogues are more active than the original lead compound, with the morphilino-substituted (9) being a more potent (IC50 = 2.8 +/- 0.10 mu M) and selective (4.6-fold) PP2A inhibitor with greater in vitro cytotoxicity (GI(50) similar to 9.6 mu M) relative to norcantharidin. The analogous thiomorpholine-substituted (10) displays increased PP1 inhibition (IC50 = 3.2 +/- 0 mu M) and reduced PP2A inhibition (IC50 = 5.1 +/- 0.41 mu M), to norcantharidin. Synthesis of the analogous cantharidin analogue (19) with incorporation of the amine nitrogen into the heterocycle further increases PP1 (IC50 = 5.9 +/- 2.2 mu M) and PP2A (IC50 = 0.79 +/- 0.1 mu M) inhibition and cell cytotoxicity (GI(50) similar to 3.3 mu M). These analogues represent the most potent cantharidin analogues thus reported. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.
Gautam Panda - One of the best experts on this subject based on the ideXlab platform.
-
I2-Mediated Diversity Oriented Diastereoselective Synthesis of Amino Acid Derived trans-2,5-Disubstituted Morpholines, Piperazines, and Thiomorpholines
2012Co-Authors: Saurav Bera, Gautam PandaAbstract:Diastereoselective trans-2,5-disubstituted amino acids derived diverse morpholines, piperazines and Thiomorpholines were prepared in 30 min-1 h with high yields through iodine-mediated 6-exotrig type cyclization from a single common synthetic intermediate. The displacement of iodine with hydride ion gave a methyl substituent at the 2-position of morpholines which provides an additional opportunity for diversity oriented nucleophilic substitution on the rings as well as incorporation of substituents at the 5-position from amino acids constituents
-
I2-mediated diversity oriented diastereoselective synthesis of amino acid derived trans-2,5-disubstituted morpholines, piperazines, and Thiomorpholines.
ACS combinatorial science, 2011Co-Authors: Saurav Bera, Gautam PandaAbstract:Diastereoselective trans-2,5-disubstituted amino acids derived diverse morpholines, piperazines and Thiomorpholines were prepared in 30 min-1 h with high yields through iodine-mediated 6-exotrig type cyclization from a single common synthetic intermediate. The displacement of iodine with hydride ion gave a methyl substituent at the 2-position of morpholines which provides an additional opportunity for diversity oriented nucleophilic substitution on the rings as well as incorporation of substituents at the 5-position from amino acids constituents.
Timothy A Hill - One of the best experts on this subject based on the ideXlab platform.
-
heterocyclic substituted cantharidin and norcantharidin analogues synthesis protein phosphatase 1 and 2a inhibition and anti cancer activity
Bioorganic & Medicinal Chemistry Letters, 2007Co-Authors: Timothy A Hill, Scott G Stewart, Benjamin Sauer, Jayne Gilbert, Stephen P Ackland, Jennette A Sakoff, Adam MccluskeyAbstract:Norcantharidin (3) is a potent PP1 (IC(50)=9.0+/-1.4 microM) and PP2A (IC(50)=3.0+/-0.4 microM) inhibitor with 3-fold PP2A selectivity and induces growth inhibition (GI(50) approximately 45 microM) across a range of human cancer cell lines including those of colorectal (HT29, SW480), breast (MCF-7), ovarian (A2780), lung (H460), skin (A431), prostate (DU145), neuroblastoma (BE2-C), and glioblastoma (SJ-G2) origin. Until now limited modifications to the parent compound have been tolerated. Surprisingly, simple heterocyclic half-acid norcantharidin analogues are more active than the original lead compound, with the morphilino-substituted (9) being a more potent (IC(50)=2.8+/-0.10 microM) and selective (4.6-fold) PP2A inhibitor with greater in vitro cytotoxicity (GI(50) approximately 9.6 microM) relative to norcantharidin. The analogous thiomorpholine-substituted (10) displays increased PP1 inhibition (IC(50)=3.2+/-0 microM) and reduced PP2A inhibition (IC(50)=5.1+/-0.41 microM), to norcantharidin. Synthesis of the analogous cantharidin analogue (19) with incorporation of the amine nitrogen into the heterocycle further increases PP1 (IC(50)=5.9+/-2.2 microM) and PP2A (IC(50)=0.79+/-0.1 microM) inhibition and cell cytotoxicity (GI(50) approximately 3.3 microM). These analogues represent the most potent cantharidin analogues thus reported.
-
heterocyclic substituted cantharidin and norcantharidin analogues synthesis protein phosphatase 1 and 2a inhibition and anti cancer activity
Bioorganic & Medicinal Chemistry Letters, 2007Co-Authors: Timothy A Hill, Scott G Stewart, Benjamin Sauer, Jayne Gilbert, Stephen P Ackland, Jennette A Sakoff, Adam MccluskeyAbstract:Norcantharidin (3) is a potent PP1 (IC50 = 9.0 +/- 1.4 mu M) and PP2A (IC50 = 3.0 +/- 0.4 mu M) inhibitor with 3-fold PP2A selectivity and induces growth inhibition (GI(50) similar to 45 mu M) across a range of human cancer cell lines including those of colorectal (HT29, SW480), breast (MCF-7), ovarian (A2780), lung (H460), skin (A431), prostate (DU145), neuroblastoma (BE2-C), and glioblastoma (SJ-G2) origin. Until now limited modifications to the parent compound have been tolerated. Surprisingly, simple heterocyclic half-acid norcantharidin analogues are more active than the original lead compound, with the morphilino-substituted (9) being a more potent (IC50 = 2.8 +/- 0.10 mu M) and selective (4.6-fold) PP2A inhibitor with greater in vitro cytotoxicity (GI(50) similar to 9.6 mu M) relative to norcantharidin. The analogous thiomorpholine-substituted (10) displays increased PP1 inhibition (IC50 = 3.2 +/- 0 mu M) and reduced PP2A inhibition (IC50 = 5.1 +/- 0.41 mu M), to norcantharidin. Synthesis of the analogous cantharidin analogue (19) with incorporation of the amine nitrogen into the heterocycle further increases PP1 (IC50 = 5.9 +/- 2.2 mu M) and PP2A (IC50 = 0.79 +/- 0.1 mu M) inhibition and cell cytotoxicity (GI(50) similar to 3.3 mu M). These analogues represent the most potent cantharidin analogues thus reported. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.
Saurav Bera - One of the best experts on this subject based on the ideXlab platform.
-
I2-Mediated Diversity Oriented Diastereoselective Synthesis of Amino Acid Derived trans-2,5-Disubstituted Morpholines, Piperazines, and Thiomorpholines
2012Co-Authors: Saurav Bera, Gautam PandaAbstract:Diastereoselective trans-2,5-disubstituted amino acids derived diverse morpholines, piperazines and Thiomorpholines were prepared in 30 min-1 h with high yields through iodine-mediated 6-exotrig type cyclization from a single common synthetic intermediate. The displacement of iodine with hydride ion gave a methyl substituent at the 2-position of morpholines which provides an additional opportunity for diversity oriented nucleophilic substitution on the rings as well as incorporation of substituents at the 5-position from amino acids constituents
-
I2-mediated diversity oriented diastereoselective synthesis of amino acid derived trans-2,5-disubstituted morpholines, piperazines, and Thiomorpholines.
ACS combinatorial science, 2011Co-Authors: Saurav Bera, Gautam PandaAbstract:Diastereoselective trans-2,5-disubstituted amino acids derived diverse morpholines, piperazines and Thiomorpholines were prepared in 30 min-1 h with high yields through iodine-mediated 6-exotrig type cyclization from a single common synthetic intermediate. The displacement of iodine with hydride ion gave a methyl substituent at the 2-position of morpholines which provides an additional opportunity for diversity oriented nucleophilic substitution on the rings as well as incorporation of substituents at the 5-position from amino acids constituents.