57234-29-4Relevant academic research and scientific papers
Dearomative enantio- and diastereoselective difluorination of resorcinol derivatives
Egami, Hiromichi,Hamashima, Yoshitaka,Otsubo, Minami,Sakimoto, Kousuke
supporting information, (2021/08/18)
We herein report enantio- and diastereoselective fluorination of naphthoresorcinol and resorcinol derivatives for the first time using a dicarboxylate phase-transfer catalyst. Stereoselective oxidative transformation of resorcinol derivatives is considered to be difficult because of their high reactivity, multiple reaction sites, and multiple hydrogen bond interactions due to the presence of the two hydroxy groups. Even though resorcinol and its oxidized frameworks are widely found in bioactive natural compounds, dearomative asymmetric fluorination of resorcinol derivatives remains unexplored. We found that our chiral dicarboxylate phase-transfer catalyst could serve as an effective catalyst for the purpose. Interestingly, naphthoresorcinols and resorcinols were converted to difluorination products preferentially rather than monofluorinated products. It is noteworthy that asymmetric desymmetrization of symmetrically substituted resorcinols occurred with up to 95% ee and the reaction was tolerant of various functional groups.
Yicathins B and C and Analogues: Total Synthesis, Lipophilicity and Biological Activities
Afonso, Carlos M. M.,Azevedo, Carlos M. G.,Bousbaa, Hassan,Ferreira, Helena,Henriques, Ana,Loureiro, Daniela R. P.,Magalh?es, álvaro F.,Neves, Nuno,Pinto, Joana,Pinto, Madalena M. M.,Reis, Salette,Soares, José X.,Vieira, Sara
supporting information, (2020/04/17)
Natural products have always been an important source of new hits and leads in drug discovery, with the marine environment being regarded as a significant source of novel and exquisite bioactive compounds. Yicathins B and C are two marine-derived xanthones that have shown antibacterial and antifungal activity. Herein, the total synthesis of these yicathins and six novel analogues is reported for the first time. As marine natural products tend to have very lipophilic scaffolds, the lipophilicity of yicathins and their analogues was evaluated in the classical octanol/water system and a biomimetic model-based system. As the xanthonic nucleus is a “privileged structure”, other biological activities were evaluated, namely antitumor and anti-inflammatory activities. An interesting anti-inflammatory activity was identified for yicathin analogues that paves the way for the design of dual activity (anti-infective and anti-inflammatory) marine-inspired xanthone derivatives.
PROCESS AND INTERMEDIATES FOR THE SYNTHESIS OF VOXELOTOR
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Page/Page column 20, (2020/07/14)
The invention relates to a process for the preparation of Voxelotor, or a salt or solvate thereof, according to the following scheme (Formula 1).
Competitive Binding Assay with an Umbelliferone-Based Fluorescent Rexinoid for Retinoid X Receptor Ligand Screening
Yamada, Shoya,Kawasaki, Mayu,Fujihara, Michiko,Watanabe, Masaki,Takamura, Yuta,Takioku, Maho,Nishioka, Hiromi,Takeuchi, Yasuo,Makishima, Makoto,Motoyama, Tomoharu,Ito, Sohei,Tokiwa, Hiroaki,Nakano, Shogo,Kakuta, Hiroki
, p. 8809 - 8818 (2019/10/11)
Ligands for retinoid X receptors (RXRs), "rexinoids", are attracting interest as candidates for therapy of type 2 diabetes and Alzheimer's and Parkinson's diseases. However, current screening methods for rexinoids are slow and require special apparatus or facilities. Here, we created 7-hydroxy-2-oxo-6-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2H-chromene-3-carboxylic acid (10, CU-6PMN) as a new fluorescent RXR agonist and developed a screening system of rexinoids using 10. Compound 10 was designed based on the fact that umbelliferone emits strong fluorescence in a hydrophilic environment, but the fluorescence intensity decreases in hydrophobic environments such as the interior of proteins. The developed assay using 10 enabled screening of rexinoids to be performed easily within a few hours by monitoring changes of fluorescence intensity with widely available fluorescence microplate readers, without the need for processes such as filtration.
Synthesis of bavachromanol from resorcinol via a tandem cationic cascade/EAS sequence
Shah, Parin A.,Wiemer, David F.
supporting information, p. 1363 - 1365 (2018/03/07)
The natural chalcone bavachromanol has been prepared through a tandem reaction sequence that joins cationic cyclization of an epoxide to an adjacent MOM-acetal with electrophilic aromatic substitution by a presumed methoxymethylene cation. Only a single regioisomer of the tandem product was observed, with substitution taking place exclusively ortho to the position of the original acetal. This regiocontrol provided a key intermediate from a symmetrical precursor, and allowed preparation of the meroterpenoid through a short reaction sequence.
A pH-responsive molecular capsule with an acridine shell: Catch and release of large hydrophobic compounds
Kishimoto, Mai,Kondo, Kei,Akita, Munetaka,Yoshizawa, Michito
supporting information, p. 1425 - 1428 (2017/02/05)
Unlike common polyaromatic hydrocarbons, acridine is a characteristic compound bearing both π-stackable large surfaces and a protonable nitrogen atom. Here we report the first synthesis of a supramolecular capsule with multiple acridine panels. In water, the assembly and disassembly of the capsule reversibly occur under neutral and acidic conditions, respectively (≥10 cycles). Notably, the pH-responsive capsule encapsulates a variety of large hydrophobic compounds (up to 1.6 nm in diameter) such as coumarins, metallophthalocyanines and subphthalocyanine in neutral water and subsequently releases them by simple addition of acid.
HYDANTOIN MODULATORS OF KV3 CHANNELS
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Page/Page column 55, (2017/07/06)
The invention provides compounds of formula (I): Said compounds being inhibitors of Kv3 channels and of use in the prophylaxis or treatment of related disorders.
Enzyme-Catalyzed Intramolecular Enantioselective Hydroalkoxylation
Gao, Shu-Shan,Garcia-Borràs, Marc,Barber, Joyann S.,Hai, Yang,Duan, Abing,Garg, Neil K.,Houk,Tang, Yi
supporting information, p. 3639 - 3642 (2017/03/20)
Hydroalkoxylation is a powerful and efficient method of forming C-O bonds and cyclic ethers in synthetic chemistry. In studying the biosynthesis of the fungal natural product herqueinone, we identified an enzyme that can perform an intramolecular enantios
Bismuth trichloride–mediated cleavage of phenolic methoxymethyl ethers
Obaro-Best, Oghale,Reed, Jack,Norfadilah, Alya A. F. B.,Monahan, Ryan,Sunasee, Rajesh
supporting information, p. 586 - 593 (2016/06/08)
A simple and efficient method for removal of phenolic methoxymethyl ethers in the presence of 30?mol% of bismuth trichloride in acetonitrile/water is described. Notable features of the cleavage protocol entail use of an ecofriendly bismuth reagent, ease of handling, low cost, operational simplicity, and good functional group compatibility. A number of structurally varied phenolic methoxymethyl ethers were cleaved in good to excellent yields.
CRYSTALLINE 2-HYDROXY-6-((2-(1-ISOPROPYL-1H-PYRAZOL-5-YL)PYRIDIN-3-YL)METHOXY)BENZALDEHYDE ANSOLVATE SALTS
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Paragraph 0062; 0065, (2015/03/16)
Disclosed are crystalline ansolvate salts of 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde (or Compound 1), such as the hydrochloride Form I.
