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Yoshiyuki Inada - One of the best experts on this subject based on the ideXlab platform.
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synthesis and thromboxane a2 prostaglandin h2 receptor antagonistic activity of phenol derivatives
Journal of Medicinal Chemistry, 1992Co-Authors: Shoji Fukumoto, Mitsuru Shiraishi, Zen-ichi Terashita, Yasuko Ashida, Yoshiyuki InadaAbstract:Consideration of possible structural similarities between thromboxane A2 and the hydroquinone form of (R)-(+)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7- phenylheptanoic acid (R-(+)-AA-2414) led to the development of a new series of thromboxane A2/prostaglandin H2 (TXA2/PGH2) receptor antagonists, namely 7-(4-fluorophenyl)-7-(2-Hydroxyphenyl)heptanoic acids (I). These compounds were found to be potent TXA2/PGH2 receptor antagonists. Compounds having either a carbonyl or a Hydroxymethyl Group at the para-position of the phenolic Hydroxy Group exhibited most potent activities in this series. Compounds 14, 15, 18, and 26 inhibited the specific binding of [3H]U-46619 to guinea pig platelet membranes (IC50 = 4.4, 80, 32, and 13 nM, respectively), and also inhibited U-46619-induced human platelet aggregation (IC50 = 310, 69, 79, and 78 nM, respectively). Comparison of the UV spectra of the compounds with a carbonyl Group at the para-position of phenolic Hydroxy Group revealed that the activity tended to increase in accordance with a decrease in the torsional angle between the carbonyl Group and the phenol ring. These results suggested that the spacial location of the carbonyl and Hydroxymethyl oxygen are important for significant increase in activity and that the carbonyl and Hydroxymethyl oxygen at the para-position of the phenolic Hydroxy Group might interact with one of the TXA2/PGH2 receptor sites.
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Synthesis and thromboxane A2/prostaglandin H2 receptor antagonistic activity of phenol derivatives.
Journal of Medicinal Chemistry, 1992Co-Authors: Shoji Fukumoto, Mitsuru Shiraishi, Zen-ichi Terashita, Yasuko Ashida, Yoshiyuki InadaAbstract:Consideration of possible structural similarities between thromboxane A2 and the hydroquinone form of (R)-(+)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7- phenylheptanoic acid (R-(+)-AA-2414) led to the development of a new series of thromboxane A2/prostaglandin H2 (TXA2/PGH2) receptor antagonists, namely 7-(4-fluorophenyl)-7-(2-Hydroxyphenyl)heptanoic acids (I). These compounds were found to be potent TXA2/PGH2 receptor antagonists. Compounds having either a carbonyl or a Hydroxymethyl Group at the para-position of the phenolic Hydroxy Group exhibited most potent activities in this series. Compounds 14, 15, 18, and 26 inhibited the specific binding of [3H]U-46619 to guinea pig platelet membranes (IC50 = 4.4, 80, 32, and 13 nM, respectively), and also inhibited U-46619-induced human platelet aggregation (IC50 = 310, 69, 79, and 78 nM, respectively). Comparison of the UV spectra of the compounds with a carbonyl Group at the para-position of phenolic Hydroxy Group revealed that the activity tended to increase in accordance with a decrease in the torsional angle between the carbonyl Group and the phenol ring. These results suggested that the spacial location of the carbonyl and Hydroxymethyl oxygen are important for significant increase in activity and that the carbonyl and Hydroxymethyl oxygen at the para-position of the phenolic Hydroxy Group might interact with one of the TXA2/PGH2 receptor sites.
Tohru Fukuyama - One of the best experts on this subject based on the ideXlab platform.
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synthesis of cardiopetaline via a wagner meerwein rearrangement without preactivation of the pivotal Hydroxy Group
Organic Letters, 2017Co-Authors: Yoshitake Nishiyama, Satoshi Yokoshima, Tohru FukuyamaAbstract:A synthesis of cardiopetaline has been accomplished via a Wagner–Meerwein rearrangement of a diol having the denudatine skeleton. The Wagner–Meerwein rearrangement could be facilitated simply by heating the diol with p-toluenesulfonic acid in pivalic acid, without preactivating the pivotal Hydroxy Group. This strategy does not require differentiation of several Hydroxy Groups in the substrate for the Wagner–Meerwein rearrangement and could be applied to the synthesis of more highly oxygenated aconitine-type diterpenoid alkaloids.
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Synthesis of Cardiopetaline via a Wagner–Meerwein Rearrangement without Preactivation of the Pivotal Hydroxy Group
2017Co-Authors: Yoshitake Nishiyama, Satoshi Yokoshima, Tohru FukuyamaAbstract:A synthesis of cardiopetaline has been accomplished via a Wagner–Meerwein rearrangement of a diol having the denudatine skeleton. The Wagner–Meerwein rearrangement could be facilitated simply by heating the diol with p-toluenesulfonic acid in pivalic acid, without preactivating the pivotal Hydroxy Group. This strategy does not require differentiation of several Hydroxy Groups in the substrate for the Wagner–Meerwein rearrangement and could be applied to the synthesis of more highly oxygenated aconitine-type diterpenoid alkaloids
Shoji Fukumoto - One of the best experts on this subject based on the ideXlab platform.
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synthesis and thromboxane a2 prostaglandin h2 receptor antagonistic activity of phenol derivatives
Journal of Medicinal Chemistry, 1992Co-Authors: Shoji Fukumoto, Mitsuru Shiraishi, Zen-ichi Terashita, Yasuko Ashida, Yoshiyuki InadaAbstract:Consideration of possible structural similarities between thromboxane A2 and the hydroquinone form of (R)-(+)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7- phenylheptanoic acid (R-(+)-AA-2414) led to the development of a new series of thromboxane A2/prostaglandin H2 (TXA2/PGH2) receptor antagonists, namely 7-(4-fluorophenyl)-7-(2-Hydroxyphenyl)heptanoic acids (I). These compounds were found to be potent TXA2/PGH2 receptor antagonists. Compounds having either a carbonyl or a Hydroxymethyl Group at the para-position of the phenolic Hydroxy Group exhibited most potent activities in this series. Compounds 14, 15, 18, and 26 inhibited the specific binding of [3H]U-46619 to guinea pig platelet membranes (IC50 = 4.4, 80, 32, and 13 nM, respectively), and also inhibited U-46619-induced human platelet aggregation (IC50 = 310, 69, 79, and 78 nM, respectively). Comparison of the UV spectra of the compounds with a carbonyl Group at the para-position of phenolic Hydroxy Group revealed that the activity tended to increase in accordance with a decrease in the torsional angle between the carbonyl Group and the phenol ring. These results suggested that the spacial location of the carbonyl and Hydroxymethyl oxygen are important for significant increase in activity and that the carbonyl and Hydroxymethyl oxygen at the para-position of the phenolic Hydroxy Group might interact with one of the TXA2/PGH2 receptor sites.
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Synthesis and thromboxane A2/prostaglandin H2 receptor antagonistic activity of phenol derivatives.
Journal of Medicinal Chemistry, 1992Co-Authors: Shoji Fukumoto, Mitsuru Shiraishi, Zen-ichi Terashita, Yasuko Ashida, Yoshiyuki InadaAbstract:Consideration of possible structural similarities between thromboxane A2 and the hydroquinone form of (R)-(+)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7- phenylheptanoic acid (R-(+)-AA-2414) led to the development of a new series of thromboxane A2/prostaglandin H2 (TXA2/PGH2) receptor antagonists, namely 7-(4-fluorophenyl)-7-(2-Hydroxyphenyl)heptanoic acids (I). These compounds were found to be potent TXA2/PGH2 receptor antagonists. Compounds having either a carbonyl or a Hydroxymethyl Group at the para-position of the phenolic Hydroxy Group exhibited most potent activities in this series. Compounds 14, 15, 18, and 26 inhibited the specific binding of [3H]U-46619 to guinea pig platelet membranes (IC50 = 4.4, 80, 32, and 13 nM, respectively), and also inhibited U-46619-induced human platelet aggregation (IC50 = 310, 69, 79, and 78 nM, respectively). Comparison of the UV spectra of the compounds with a carbonyl Group at the para-position of phenolic Hydroxy Group revealed that the activity tended to increase in accordance with a decrease in the torsional angle between the carbonyl Group and the phenol ring. These results suggested that the spacial location of the carbonyl and Hydroxymethyl oxygen are important for significant increase in activity and that the carbonyl and Hydroxymethyl oxygen at the para-position of the phenolic Hydroxy Group might interact with one of the TXA2/PGH2 receptor sites.
Barend C B Bezuidenhoudt - One of the best experts on this subject based on the ideXlab platform.
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al otf 3 catalyzed sn2 substitution of the β Hydroxy Group in morita baylis hillman adducts with indoles
ChemInform, 2015Co-Authors: Mukut Gohain, Shunhuang Lin, Barend C B BezuidenhoudtAbstract:A simple, efficient, and cost-effective process for the synthesis of C3-alkylated indole derivatives by SN2′ substitution of the Hydroxy Group in β-Hydroxyketones with indoles, is described.
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al otf 3 catalyzed sn2 substitution of the β Hydroxy Group in morita baylis hillman adducts with indoles
Tetrahedron Letters, 2015Co-Authors: Mukut Gohain, Shunhuang Lin, Barend C B BezuidenhoudtAbstract:The Al(OTf)3-catalyzed SN2′-type substitution of the β-Hydroxy Group in Morita–Baylis–Hillman adducts with indoles is reported. The reaction proceeded efficiently with aryl-, heteroaryl-, aliphatic- and alicyclic-containing β-Hydroxyketones and a variety of substituted indoles.
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al otf 3 an efficient recyclable catalyst for direct nucleophilic substitution of the Hydroxy Group of propargylic alcohols with carbon and heteroatom centered nucleophiles to construct c c c o c n and c s bonds
Tetrahedron Letters, 2012Co-Authors: Mukut Gohain, Charlene Marais, Barend C B BezuidenhoudtAbstract:Abstract A general and highly efficient Al(OTf)3-catalyzed methodology has been developed for the direct nucleophilic substitution of the Hydroxy Group in propargylic alcohols with a variety of carbon- and heteroatom-centered nucleophiles such as alcohols, aromatic compounds, amides, and thiols, leading to the construction of C–C, C–O, C–N and C–S bonds.
Hiroki Takahata - One of the best experts on this subject based on the ideXlab platform.
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acceleration effect of an allylic Hydroxy Group on ring closing enyne metathesis of terminal alkynes scope application and mechanistic insights
Chemistry: A European Journal, 2008Co-Authors: Tatsushi Imahori, Hidetomo Ojima, Yuichi Yoshimura, Hiroki TakahataAbstract:An interesting acceleration effect of an allylic Hydroxy Group on ring-closing enyne metathesis has been found. Ring-closing enyne metathesis of terminal alkynes possessing an allylic Hydroxy Group proceeded smoothly without the ethylene atmosphere generally necessary to promote the reaction. The synthesis of (+)-isofagomine with the aid of this efficient reaction has been demonstrated. Mechanistic studies of the acceleration effect were also carried out. Results of NMR studies suggested that the reaction proceeded via an "ene-then-yne" pathway. Kinetic studies indicated switching of the rate-determining step as a consequence of the presence of an allylic Hydroxy Group. These results suggest acceleration of the reentry step of Ru-carbene species by the allylic Hydroxy Group.
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acceleration effect of allylic Hydroxy Group on ring closing enyne metathesis of terminal alkynes scope and application to the synthesis of isofagomine
Tetrahedron Letters, 2008Co-Authors: Tatsushi Imahori, Hidetomo Ojima, Hiroki Tateyama, Yukiko Mihara, Hiroki TakahataAbstract:An interesting allylic substituent effect on ring-closing enyne metathesis has been found. An allylic Hydroxy Group on enyne substrates accelerates ring-closing enyne metathesis of terminal alkynes. The reaction proceeds smoothly without ethylene atmosphere and/or more reactive newer generation Ru-carbene catalysts, which are generally necessary to promote the reaction. This efficient reaction was applied to the synthesis of isofagomine.
