7249-16-3Relevant articles and documents
Preparation process of dihydrooat alkaloid D
-
Paragraph 0045-0052; 0065-0069, (2021/06/13)
The invention relates to a preparation process of dihydrooat alkaloid D. The preparation process comprises the following three steps: phenolic hydroxyl group protection, acylating chlorination and amidation, and hydrolysis deprotection, wherein p-hydroxyp
Herba portulacae amide and purpose thereof
-
Paragraph 0039-0042, (2020/12/08)
The invention relates to the technical field of cosmetics, in particular to a herba portulacae amide and a purpose thereof. A compound capable of resisting inflammation, resisting histamine, resistingoxidization and whitening is prepared, and therefore, t
Ligand-Controlled Regioselective Hydrocarboxylation of Styrenes with CO2 by Combining Visible Light and Nickel Catalysis
Meng, Qing-Yuan,Wang, Shun,Huff, Gregory S.,Konig, Burkhard
supporting information, p. 3198 - 3201 (2018/03/13)
The ligand-controlled Markovnikov and anti-Markovnikov hydrocarboxylation of styrenes with atmospheric pressure of CO2 at room temperature using dual visible-light-nickel catalysis has been developed. In the presence of neocuproine as ligand, the Markovnikov product is obtained exclusively, while employing 1,4-bis(diphenylphosphino)butane (dppb) as the ligand favors the formation of the anti-Markovnikov product. A range of functional groups and electron-poor, -neutral, as well as electron-rich styrene derivatives are tolerated by the reaction, providing the desired products in moderate to good yields. Preliminary mechanistic investigations indicate the generation of a nickel hydride (H-NiII) intermediate, which subsequently adds irreversibly to styrenes.
Hemisynthesis, Antitumoral Effect, and Molecular Docking Studies of Ferutinin and Its Analogues
Safi, Rmi,Rodriguez, Frderic,Hilal, Georges,Diab-Assaf, Mona,Diab, Youssef,El-Sabban, Marwan,Najjar, Fadia,Delfourne, Evelyne
, p. 382 - 397 (2016/03/12)
The natural product ferutinin was shown to act as an agonist to estrogen receptor ERα and agonist/antagonist to ERβ featuring a weak antiproliferative activity toward breast cancer cells. To enhance this activity, ferutinin analogues were synthesized by e
Synthesis of a novel diarylheptanoid isolated from Zingiber officinale
Parker, Gregory D.,Seden, Peter T.,Willis, Christine L.
scheme or table, p. 3686 - 3689 (2009/10/04)
Syntheses of 4-acetoxy-2,6-disubstituted tetrahydropyrans via Prins cyclisation of homoallylic alcohols with benzylic aldehydes are described and the methodology is applied in the total synthesis of diarylheptanoid 1 confirming both the structure and abso
Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone
Kiviranta, Paeivi H.,Salo, Heikki S.,Leppaenen, Jukka,Rinne, Valtteri M.,Kyrylenko, Sergiy,Kuusisto, Erkki,Suuronen, Tiina,Salminen, Antero,Poso, Antti,Lahtela-Kakkonen, Maija,Wallen, Erik A.A.
, p. 8054 - 8062 (2008/12/23)
SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors.
Design and evaluation of hydroxamate derivatives as metal-mediated inhibitors of a protein tyrosine kinase
Gu, Xianfeng,Wang, Yuehao,Kumar, Anil,Ye, Guofeng,Parang, Keykavous,Sun, Gongqin
, p. 7532 - 7539 (2008/02/01)
Protein tyrosine kinases use two Mg2+ ions as cofactors in catalysis, one as the ATP-Mg complex (M1) and the other as an essential activator (M2), The M2-binding site has high affinity for transition metal cations such as cobalt and zinc. Takin
Stereoselectivity control by oxaspiro rings during Diels-Alder cycloadditions to cross-conjugated cyclohexadienones: The syn oxygen phenomenon
Ohkata, Katsuo,Tamura, Yukiko,Shetuni, Brandon B.,Takagi, Ryukichi,Miyanaga, Wataru,Kojima, Satoshi,Paquette, Leo A.
, p. 16783 - 16792 (2007/10/03)
The diastereofacial selectivity operating in Diels-Alder additions involving spirocyclic cross-conjugated cyclohexadienones with dienes of varying reactivity has been investigated. The study has included the ether series 1a-c as well as the lactone/ketone pair 2a/2b. In all cases, the preferred [4+2] cycloaddition pathway consisted of bonding from that π-surface syn to the oxygen atom. 4-Substituted-4-methyl-2,5-cyclohexadienones (monocyclic systems) were also examined and found to undergo bond formation preferentially from the face bearing the more electron-withdrawing of the two groups at the 4 position. Kinetic parameters were determined for the cycloaddition of 1a and 2a to cyclopentadiene. The rate acceleration profile of solvents was in the order CF3CH2OH ? CH3CN～CH2Cl 2 for the production of 9a from 1a and CF3CH2OH ? CH2Cl2 > CH3CN for the production of 21a from 2a, respectively. This spread in polarity had no major impact on product distribution, a phenomenon also reflected in the behavior of 4-substituted-4-methyl-2,5-cyclohexadienones under comparable conditions. Theoretical assessment of these experimental facts was undertaken at the HF/6-31G* level. The facial selectivity is understandable in terms of the secondary interaction between the HOMO of the diene and LUMO of the dienophile as well as the effective hyperconjugation between the newly forming bond and the 4-anti-C-C σ-orbital due to the more electron-donating bond, as defined by the Cieplak model.
Design, synthesis, and proposed active site binding analysis of monocyclic 2-azetidinone inhibitors of prostate specific antigen
Adlington,Baldwin,Becker,Chen,Cheng,Cooper,Hermann,Howe,McCoull,McNulty,Neubauer,Pritchard
, p. 1491 - 1508 (2007/10/03)
A homology derived molecular model of prostate specific antigen (PSA) was created and refined. The active site region was investigated for specific interacting functionality and a binding model postulated for the novel 2-azetidinone acyl enzyme inhibitor 1 (IC50 = 8.98 ± 0.90 μM) which was used as a lead compound in this study. A single low energy conformation structure II (Figure 2) was adopted as most likely to represent binding after minimization and dynamics calculations. Systematic analysis of the binding importance of all three side chains appended to the 2-azetidinone was conducted by the synthesis of several analogues. A proposed salt bridge to Lys-145 with 4 (IC50 = 5.84 ± 0.92 μM) gave improved inhibition, but generally the binding of the N-1 side chain in a specific secondary aromatic binding site did not tolerate much structural alteration. A hydrophobic interaction of the C-4 side chain afforded inhibitor 6 (IC50 = 1.43 ± 0.19 μM), and polar functionality could also be added in a proposed interaction with Gln-166 in 5 (IC50 = 1.34 ± 0.05 μM). Reversal of the C-4 ester connectivity furnished inhibitors 7 (IC50 = 1.59 ± 0.15 μM), 11 IC50 = 3.08 ± 0.41 μM) and 13 (IC50 = 2.19 ± 0.36 Mμ) which were perceived to bind to PSA by a rotation of 180° relative to the C-4 ester of normal connectivity. Incorporation of hydroxyl functionality into the C-3 side chain provided 16 IC50 = 348 ± 50 nM) with the greatest increase in PSA inhibition by a single modification. Multiple copy simultaneous search (MCSS) analysis of the PSA active site further supported our model and suggested that 18 would bind strongly. Asymmetric synthesis yielded 18 (IC50 = 226 ± 10 nM) as the most potent inhibitor of PSA reported to date. It is concluded that our design approach has been successful in developing PSA inhibitors and could also be applied to the inhibition of other enzymes, especially in the absence of crystallographic information.
Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ
Yang, Dan,Wong, Man-Kin,Yan, Zheng
, p. 4179 - 4184 (2007/10/03)
A novel method for regioselective oxidation of phenols and anisoles has been developed in which dioxiranes, generated in situ from ketones and Ozone, oxidize phenol derivatives in an intramolecular fashion. A series of ketones with electron-withdrawing groups, such as CF3, COOMe, and CH2Cl, were attached to phenols, anisoles, or aryl rings via a C2 or C3 methylene linker. In a homogeneous solvent system of CH3CN and H2O, oxidation of phenol derivatives 1-10 afforded spiro 2-hydroxydienones in 24-55% yields regardless of the presence of other substituents (ortho Me, meta Me or Br) on the aryl ring and the length of the linker. Experimental evidences were provided to support the mechanism that involves a regioselective π bond epoxidation of aryl rings followed by epoxide rearrangement and hemiketal formation.
