19722-76-0Relevant academic research and scientific papers
Variable-Temperature NMR Studies of 2,6-Dihydroxy Acylaromatic Compounds. Deuterium Isotope Effects on Chemical Shifts, Isotopic Perturbation of Equilibrium and Barriers to Rotation
Hansen, Poul Erik,Christoffersen, Morten,Bolvig, Simon
, p. 893 - 902 (1993)
A series of 2,6-dihydroxy acylaromatic compounds were investigated to characterize the rotational and hydrogen bonding properties of the carbonyl group.Deuterium isotope effects on 1H and 13C chemical shifts due to deuteriation of OH groups were determined at both ambient and low temperature.In the latter case isotope effects on chemical shifts of the individual rotamers can be determined.Deuteriation of one of the OH groups may lead to isotopic perturbation of the tautomeric equilibrium of the carbonyl group and the two hydroxyl groups.The perturbation was found to be larger in ketones than in esters.Complete band shape analysis of the OH resonance of the esters and ketones in a temperature interval above and below the coalescence temperature led to ΔG(excit.), ΔH(excit.) and ΔS(excit.) values for various concentrations of added THF-d8. ΔS(excit.) was found to be strongly negative.Temperature coefficients for the shift of the OH resonances showed large variations for esters and ketones owing to the different hydrogen bond patterns.The esters have two intramolecular hydrogen bonds, one strong and an additional weaker one between the OH and OR groups.The second OH group of the ketones was shown to point primarily towards C-5.Increasing amounts of THF-d8 increased the amount of this rotamer.The anisotropy of the XC=O group at C-2, C-6 was shown to lead to a low-field shift of C-2, very different from that found for C=O groups without hydrogen bonds.The anisotropy caused by OH groups can also be estimated.On the basis of the thermodynamic parameters, a model for the rotation of the ester group is suggested.The rate-determining step involves both intramolecular hydrogen bonds, which are twisted out of the ring plane to form hydrogen bonds to the solvent or other hydrogen bond acceptors.
Enantioselective Total Synthesis of Berkeleyone A and Preaustinoids
Franzoni, Ivan,Guo, Chuning,Hong, Benke,Ji, Yunpeng,Jia, Hongli,Li, Houhua,Zhang, Yang
supporting information, p. 14869 - 14874 (2021/05/27)
Herein we report the first enantioselective total synthesis of 3,5-dimethylorsellinic acid-derived meroterpenoids (?)-berkeleyone A and its five congeners ((?)-preaustinoids A, A1, B, B1, and B2) in 12–15 steps, starting from commercially available 2,4,6-trihydroxybenzoic acid hydrate. Based upon the recognition of latent symmetry within D-ring, our convergent synthesis features two critical reactions: 1) a symmetry-breaking, diastereoselective dearomative alkylation to assemble the entire carbon core, and 2) a Sc(OTf)3-mediated sequential Krapcho dealkoxycarbonylation/carbonyl α-tert-alkylation to forge the intricate bicyclo[3.3.1]nonane framework. We also conducted our preliminary biomimetic investigations and uncovered a series of rearrangements (α-ketol, α-hydroxyl-β-diketone, etc.) responsible for the biomimetic diversification of (?)-berkeleyone A into its five preaustinoid congeners.
COMBINATION TREATMENT OF BACTERIAL INFECTION
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Paragraph 0115; 0116, (2020/06/08)
The present invention resides in the discovery that combined use of kuraridin (or any one of its analogs) and epicatechin gallate (ECG) can provide heightened level of antimicrobial activity, especially for the suppression of bacteria of the Staphylococcus aureus and Staphylococcal species. Compositions, kits, and methods for the combination use are disclosed.
Natural-Product-Inspired Compounds as Countermeasures against the Liver Carcinogen Aflatoxin B1
Carter, Adam C.,King, Jarrod B.,Mattes, Allison O.,Cai, Shengxin,Singh, Narender,Cichewicz, Robert H.
, p. 1694 - 1703 (2019/06/08)
Aflatoxin B1 (AfB1) ranks among the most potent liver carcinogens known, and the accidental or intentional exposure of humans and livestock to this toxin remains a serious global threat. One protective measure that had been proposed is employing small-molecule therapeutics capable of mitigating the toxicity of AfB1; however, to date, these efforts have had little clinical success. To identify molecular scaffolds that reduce the toxicity of AfB1, we developed a cell-based high-throughput high-content imaging assay that enabled our team to test natural products (pure compounds, fractions, and extracts) for protection of monolayers and spheroids composed of HepG2 liver cells against AfB1. The spheroid assay showed notable potential for further development, as it afforded greater sensitivity of HepG2 cells to AfB1, which is believed to better mimic the in vivo response of hepatocytes to the toxin. One of the most bioactive compounds to arise from this investigation was alternariol-9-methyl ether (1, purified from an Alternaria sp. isolate), which inspired the synthesis and testing of several structurally related molecules. Based on these findings, it is proposed that several types of natural and synthetic polyarene molecules that have undergone oxidative functionalization (e.g., compounds containing 3-methoxyphenol moieties) are promising starting points for the development of new agents that protect against AfB1 toxicity.
Biomimetic Synthesis of Complex Flavonoids Isolated from Daemonorops “Dragon's Blood”
Schmid, Matthias,Trauner, Dirk
supporting information, p. 12332 - 12335 (2017/09/25)
The dragonbloodins are a pair of complex flavonoid trimers that have been isolated from the palm tree Daemonorops draco, one of the sources of the ancient resin known as “dragon's blood”. We present a short synthesis that clarifies their relative configur
Total synthesis of 7′,8′-dihydroaigialospirol
Yuen, Tsz-Ying,Brimble, Margaret A.
supporting information, p. 5154 - 5157 (2013/01/15)
A highly convergent total synthesis of 7′,8′- dihydroaigialospirol is described. Key steps of the synthesis include a Nozaki-Hiyama-Kishi (NHK) coupling of an iodoalkyne with an advanced phthalide-aldehyde and a remarkable one-pot acid-mediated global deprotection/spiroacetalization.
Fast and efficient synthesis of the complete LL-Z1640-2 framework
Henry, Neil,Robertson, Murray N.,Marquez, Rodolfo
, p. 6088 - 6091 (2008/03/12)
The convergent synthesis of the complete LL-Z1640-2 framework has been completed. This fast and efficient approach provides flexible access into the resorcyclic lactones.
Selective protein tyrosine phosphatatase inhibitors
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, (2008/06/13)
Compounds of formula (I) or therapeutically acceptable salts thereof, are selective protein tyrosine kinase-B (PTP1B) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of disorders using the compounds are disclosed.
Selective protein tyrosine phosphatatase inhibitors
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, (2008/06/13)
Compounds of formula (I) or therapeutically acceptable salts thereof, are selective protein tyrosine kinase-B (PTP1B) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of disorders using the compounds are disclosed.
Trimethoxyphenyl Compounds, XI. Constituents of Hagenia abyssinica, 2: Synthesis of Phloracylophenones Containing One Phloroglucinol Unit
Schiemenz, Guenter Paulus,Behrens, Heinz,Ebert, Claus Peter,Maienschein, Konrad,Schroeder, Jens-Michael
, p. 681 - 692 (2007/10/02)
For the Koso constituents K6 and K8, we previously proposed the structures 1a, b and 2a, b.These assignments have been confirmed by synthesis. - Keywords: Flores koso, Revised Structure, Synthesis of Phloroglucinols
