49855-03-0Relevant articles and documents
Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation
Tao, Lin,Zhao, Qingyang,Zhang, Xumu,Dong, Xiu-Qin
, p. 1859 - 1862 (2020/01/21)
Rh/ZhaoPhos-catalyzed asymmetric hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities (up to 99percent yield, 98percent ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 molpercent catalyst loading (TON = 5000), the hydrogenation product was easily converted to access other important compounds, which demonstrated the synthetic utility of this asymmetric catalytic methodology.
Copper(ii)-catalyzed C-O coupling of aryl bromides with aliphatic diols: Synthesis of ethers, phenols, and benzo-fused cyclic ethers
Liu, Yajun,Park, Se Kyung,Xiao, Yan,Chae, Junghyun
, p. 4747 - 4753 (2014/06/24)
A highly efficient copper-catalyzed C-O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(ii) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers in good to excellent yields. In this newly developed protocol, aliphatic diols have multilateral functions as coupling reactants, ligands, and solvents. The resulting hydroxyalkyl aryl ethers were further readily converted into the corresponding phenols, presenting a valuable alternative way to phenols from aryl bromides. Furthermore, it was demonstrated that they are useful intermediates for more advanced molecules such as benzofurans and benzo-fused cyclic ethers. This journal is
Anti-inflammatory activities of selected synthetic homoisoflavanones
Shaikh, Mahidansha M.,Kruger, Hendrik G.,Bodenstein, Johannes,Smith, Peter,Du Toit, Karen
experimental part, p. 1473 - 1482 (2012/09/22)
Four homoisoflavanones of the 3-benzylidene-4-chromanone type, some of which were previously isolated from Caesalpinia pulcherrima, were synthesised to determine their anti-inflammatory activity and cytotoxicity. A range of four different homoisoflavanones (compounds 4a-4d) were synthesised from the corresponding substituted phenols.1H-and 13C-NMR data together with high-resolution mass spectroscopy data were employed to elucidate the structures. Anti-inflammatory activity was determined in mice with acute croton oil-induced auricular dermatitis. Invitro cytotoxicity was tested against a Chinese hamster ovarian cell line using the 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazoliumbromide (MTT) assay. Compound 4a exhibited a tendency to inhibit oedema in a dose-dependent manner after 3 and 6 h of treatment. Compounds 4b-4d also inhibited oedema, although a clear dose-response relationship was not observed. Compounds 4a-4c were found to be less cytotoxic than compound 4d. Compound 4b was the least cytotoxic. Compounds 4a-4d exhibited anti-inflammatory activity and varying levels of cytotoxicity.
(1,4-DIAZA-BICYCLO[3.2.2]NON-6-EN-4-YL)-HETEROCYCLYL-METHANONE LIGANDS FOR NICOTINIC ACETYLCHOLINE RECEPTORS, USEFUL FOR THE TREATMENT OF DISEASE
-
Page/Page column 59; 60, (2009/05/30)
The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds, which act as ligands for the a7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof. The novel compounds include compounds of formula I: (I) wherein X, R1, and R2 are as herein defined.
Chemoenzymatic synthesis and resolution of compounds containing a quaternary stereocenters adjacent to a carbonyl group
Mahapatra, Tridib,Jana, Nandan,Nanda
, p. 1224 - 1232 (2008/09/21)
Racemic compounds containing a quaternary stereocenter (having hydroxymethyl and alkyl group adjacent to keto functionality) based on chromanone, α-tetralone, and indalone scaffolds have been synthesized. An enzymatic irreversible transesterification approach has been applied to generate the pure enantiomers in a stereocontrolled fashion. The pure enantiomers of some α,α-dialkylated carbonyl compounds have been synthesized by this method.
Enantioselective enzymatic desymmetrization of prochiral 1,3-diols and enzymatic resolution of monoprotected 1,3-diols based on α-tetralone and related multifunctional scaffolds
Mahapatra, Tridib,Das, Tapas,Nanda, Samik
body text, p. 2497 - 2507 (2009/04/11)
Novel multifunctional chemotypes based on α-tetralone, α-indanone, and chromanone have been synthesized by a chemo-enzymatic approach by applying an enzymatic irreversible transesterification strategy. The scaffolds synthesized can be further elaborated with subsequent enzymatic as well as chemical transformations for the generation of new sets of structurally related organic molecules.
ERβ ligands. Part 6: 6H-Chromeno[4,3-b]quinolines as a new series of estrogen receptor β-selective ligands
Vu, An T.,Campbell, Alison N.,Harris, Heather A.,Unwalla, Rayomand J.,Manas, Eric S.,Mewshaw, Richard E.
, p. 4053 - 4056 (2008/02/08)
A new class of estrogen receptor beta (ERβ) ligands based on the 6H-chromeno[4,3-b]quinoline scaffold has been prepared. Several C7-substituted analogues displayed high affinity and modest selectivity for ERβ.
6H-[1]benzopyrano[4,3-b]quinolines and their use as estrogenic agents
-
Page/Page column 7; 10, (2010/10/20)
This invention provides 6H-[1]benzopyrano[4,3-b]quinoline compounds having the formula I: The invention further provides compositions including the compounds, methods for the use of the compounds, and methods of preparation of the compounds.
Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids
Siddaiah, Vidavalur,Rao, Chunduri Venkata,Venkateswarlu, Somepalli,Krishnaraju, Alluri V.,Subbaraju, Gottumukkala V.
, p. 2545 - 2551 (2007/10/03)
A series of four naturally occurring homoisoflavonoids and eight analogs have been synthesized starting from an appropriately substituted phenol through chroman-4-one, in four steps. The products were assigned as E-isomers based on NMR spectroscopic data.
Synthesis of 3-(p-Halobenzyl)-4-aryl-2H-chromenes as Selective Ligands for Antiestrogen-binding Sites.
Srikanth, Natarajan,Kon, Oi-Lian,Ng, Siu-Choon,Sim, Keng-Yeow
, p. 1412 - 1422 (2007/10/03)
A series of basic ethers of 3-(p-halobenzyl)-4-aryl-2H-chromenes was synthesised from a common precursor, the corresponding 3-benzylidenechromanones (homoisoflavanones), by two routes.The three-step first route involves the reduction of the 3-benzylidenec
