642-71-7Relevant academic research and scientific papers
In vitro antiplasmodial activity of extracts of tristaniopsis species and identification of the active constituents: Ellagic acid and 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-O-/?-D-glucopyranoside
Verotta, Luisella,Dell'Agli, Mario,Giolitot, Andrea,Guerrini, Marco,Cabalion, Pierre,Bosisio, Enrica
, p. 603 - 607 (2001)
Screening of plants from New Caledonia for antiplasmodial activity against Plasmodium falciparum revealed that methanolic extracts of the leaves and bark of Tristaniopsis calobuxus, T. yateensis, and T. glauca inhibited the growth of chloroquine-sensitive and -resistant clones. Ellagic acid and the new compound 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-O-β-D-glucopyranoside were identified as the active constituents (ICso 0.5 and 3.2 /M, respectively). The growth inhibition of both clones was comparable. The compounds showed negligible or very low cytotoxicity to human skin fibroblasts and Hep G2 cells when tested at concentrations ranging from 0.5 to 100 πM.
Benzophenone Glucosides and B-Type Proanthocyanidin Dimers from Zambian Cassia abbreviata and Their Trypanocidal Activities
Choongo, Kennedy,Ishikawa, Yoshinobu,Kikuchi, Takashi,Munsimbwe, Linous,Murata, Toshihiro,Shirakura, Izumi,Suganuma, Keisuke
, p. 91 - 104 (2022/01/20)
Two benzophenone glucosides (1 and 2), five flavan-3-ol dimers (5–9), and 17 known compounds (3, 4, and 10–24) were identified from the bark extract of Cassia abbreviata. The chemical structures display two points of interest. First, as an unusual charact
Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives
Li, Wei,Liu, Kexiong,Su, Liang,Wang, Qiuan
supporting information, (2021/08/12)
A series of 5,6,7-trimethoxyflavones 1a-1g and their derivatives 2a-2g, 3a-3d, 4 and 5, including the natural products 5,6,7-trimethoxy-4’-hydroxyflavone (1a), 5,6,7,3’,4’ -pentamethoxyflavone (sinensetin, 1 b), 5,6,7-trimethoxy-3’,4’-methyl enedioxy flavone (1c), 5,6,7,3’-tetramethoxy-4,5’-methylenedioxyflavone (1e), 5,6,7, 3’,4’,5’-hextamethoxyflavone (1 g), 5-hydroxy-3,4,2’,3’,4’-pentamethoxy chal-cone (2 b), 5,4’-dihydroxy-6,7-dimethoxy flavone (cirsimaritin, 3a) and 5-hydroxy-6,7,3’, 4’-tetramethoxyflavone (5-demethylsinensetin, 3 b), 3,5,6,7,3’,4’-hexamethoxyflavone (3-methoxysinensetin, 4) and 5’-hydroxy-3,6,7,3’,4’-pentamethoxyflavone (5) were synthesized. Their anti-proliferative activity in?vitro was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2 and SUN-5) by the CTG assay. The results showed that most of the synthetic compounds exhibited moderate to high anti-proliferative activities. In particular, compound 3c possess IC50 (5.30 μM) values below 10 μM against Aspc-1 cells and are worthy of further investigation.
Rongalite-promoted metal-free aerobic ipso-hydroxylation of arylboronic acids under sunlight: DFT mechanistic studies
Golla, Sivaparwathi,Poshala, Soumya,Pawar, Ravinder,Kokatla, Hari Prasad
supporting information, (2019/12/27)
A novel rongalite-promoted metal-free aerobic ipso-hydroxylation of arylboronic acids has been developed. This method employs low-cost rongalite as a radical initiator and O2 as a green oxidizing agent for ipso-hydroxylation. This protocol is compatible with a wide variety of functional groups with good to excellent yields at room temperature. Furthermore, mechanistic insight into the role of superoxide radical anions in C-B cleavage has also been provided based on DFT studies.
A convenient synthesis of phenols
Kristianslund, Renate,Vik, Anders,Hansen, Trond V.
supporting information, p. 2809 - 2814 (2018/12/04)
Anilines are rapidly, often within 60 minutes, converted into the corresponding phenols in up to 87% isolated yield. The presented experimentally simple protocol display broad compatibility with a variety of functional groups, and in particular, well suited for the preparation of methyl-substituted phenols. Such phenols are not easily available by other synthetic approaches. The formation of phenolic radical coupling products was not observed even for activated anilines using this open flask method.
Accessing Polyoxygenated Dibenzofurans via the Union of Phenols and o-Benzoquinones: Rapid Syntheses of Metabolites Isolated from Ribes takare
Zhang, Meng Yao,Barrow, Russell A.
supporting information, p. 2302 - 2305 (2017/05/12)
The construction of polyoxygenated dibenzo[b,d]furan frameworks from the union of substituted phenols/naphthols and o-benzoquinones via a Michael-oxidation-oxa-Michael cascade is reported. The power of this transformation is demonstrated in the generation of a library of highly substituted dibenzofurans, featuring specifically substituted molecules containing broad ranges of functionality. The utility of this method is showcased in the total syntheses of two dibenzofurans isolated from Ribes takare, assembling the carbon scaffold of both natural products in one operation.
Ga(OTf)3-mediated synthesis of substituted benzofurans
Wang, Heui-Sin,Chan, Chieh-Kai,Chang, Meng-Yang
, p. 5132 - 5141 (2016/07/25)
A synthetic procedure, for the synthesis of a series of functionalized benzofurans 3–5 and benzonaphthofurans 6, starting from intermolecular O-alkylation of α-bromoaryl ketones 2 with potassium oxygenated phenoxides 1 followed by Ga(OTf)3-catalyzed direct intramolecular cyclodehydration of the resulting α-aryloxyaryl ketones, has been developed. The use of various metal triflates was investigated for a facile approach and efficient transformation. Pentacyclic benzophenanthrofurans 7 were prepared via photolytic annulations of 5.
Two new glycosides from Duboscia macrocarpa Bocq.
Tchuendem, Marguerite H.K.,Douanla, Pascal D.,Tabopda, Turibio K.,Tchinda, Alembert T.,Tamze, Véronique,Nkengfack, Augustin E.,Abegaz, Berhanu M.,Connolly, Joseph D.
, p. 1 - 4 (2014/12/10)
Two new compounds namely dubosciasides A (1) and B (2) were isolated from stem bark of Duboscia macrocarpa Bocq. together with three known flavonoids. Their structures were determined by spectroscopic methods including one- and two-dimensional NMR, EIMS and HRESIMS. The new compounds were identified as 6-C-β-d-apiofuranosyl-(1 → 4)-β-d-galactopyranosylnaringetol (1) and 1-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-xylopyranosyl-3,4,5-trimethoxyphenol (2).
Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst
Cheung, Chi Wai,Buchwald, Stephen L.
, p. 5351 - 5358 (2014/06/23)
A method for the hydroxylation of aryl and heteroaryl halides, promoted by a catalyst based on a biarylphosphine ligand tBuBrettPhos (L5) and its corresponding palladium precatalyst (1), is described. The reactions allow the cross-coupling of both potassium and cesium hydroxides with (hetero)aryl halides to afford a variety of phenols and hydroxylated heteroarenes in high to excellent yield.
Synthesis of polyalkoxy-3-(4-methoxyphenyl)coumarins with antimitotic activity from plant allylpolyalkoxybenzenes
Tsyganov, Dmitry V.,Chernysheva, Natalia B.,Salamandra, Lev K.,Konyushkin, Leonid D.,Atamanenko, Olga P.,Semenova, Marina N.,Semenov, Victor V.
, p. 147 - 149 (2013/07/26)
Novel polyalkoxy-3-(4-methoxyphenyl)coumarins - analogues of natural antimitotic compounds - were synthesized from plant allylpolyalkoxybenzenes and tested in vivo in the phenotypic sea urchin embryo assay for antiproliferative antitubulin activity.
