303224-34-2Relevant articles and documents
NHC-catalyzed green synthesis of functionalized chromones: DFT mechanistic insights and: In vitro activities in cancer cells
Murugesh, Nithya,Haribabu, Jebiti,Arumugam, Krishnamoorthy,Balachandran, Chandrasekar,Swaathy, Rajagopal,Aoki, Shin,Sreekanth, Anandaram,Karvembu, Ramasamy,Vedachalam, Seenuvasan
supporting information, p. 13509 - 13525 (2019/09/06)
An efficient synthesis of 3-aminochromones and 3-alkylchromones by a N-heterocyclic carbene (NHC) catalyzed intramolecular hydroacylation reaction of corresponding salicylaldehyde derived nitriles and activated alkynes respectively in ionic liquids under microwave conditions is reported. This protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, and convenient operation using the commercially available thiazolium catalyst. The origin of the chemical reactivity of the NHC-catalyzed intramolecular hydroacylation reaction of nitriles is studied using Density Functional Theory (DFT). The results suggest that 3-aminochromone formation occurs via an acyl anion intermediate called a Breslow intermediate (INT2) through TS2. The Breslow intermediate (INT2) forms a carbon-carbon bond with the nitrile carbon to produce an imine intermediate INT3viaTS3, which further undergoes imine to amine tautomerism to give the end product. Some of the derivatives of 3-aminochromone are subjected to amine functionalization in one pot to obtain a library of compounds for anticancer activity. Among the investigated compounds, 2c (SVM-2), 4c (SVM-4) and 2d (SVM-9) show IC50 values of 5.18, 4.89 and 27.3 μM respectively in HeLa S3 cancer cells. Compound 5c (SVM-5) shows IC50 values of 13.3 and 14.2 μM in A549 and HeLa S3 cancer cells, respectively. Compounds 2c (SVM-2) and 4c (SVM-4) produce morphological changes and control the colony formation in HeLa S3 cells, which indicates that these small molecules are potential candidates for anticancer drugs.
Preparation and application of ruthenium metal olefin metathesis catalyst
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Paragraph 0156-0161, (2017/08/31)
The invention discloses a ruthenium metal olefin metathesis catalyst formed by a novel olefin ligand and ruthenium Cabbeen and application thereof. Easily-obtained substituted salicylaldehyde with a simple structure is used as a starting material for simple synthesis to obtain a required olefin ligand, and the corresponding novel ruthenium metal catalyst can be obtained by ligand exchange between the olefin ligand and a catalyst precursor. The catalyst can efficiently catalyze olefin metathesis and catalyze ring-closing metathesis of various dienes to obtain ring compounds and ring-opening metathesis polymerization of dicyclopentadiene. The method is easily-obtained in raw materials, simple in operation, stable in process, environmental friendly, and suitable for amplification production, and a very good method and idea is provided for preparing various macrocyclic drug molecules and super-performance polymer materials by use of the olefin metathesis catalyst.
N-heterocyclic carbene-catalyzed intramolecular aldehyde-nitrile cross coupling: An easy access to 3-aminochromones
Vedachalam, Seenuvasan,Zeng, Jing,Gorityala, Bala Kishan,Antonio, Meraldo,Liu, Xue-Wel
supporting information; experimental part, p. 352 - 355 (2010/03/24)
(Figure presented) An immense effort has been made to develop an efficient strategy for the carbon-carbon bond formation between aldehyde and nitrile intramolecularly using an N-heterocyclic carbene catalyst to derive 3-aminochromone derivatives In good to excellent yields (80-95%).
Therapeutic uses of di-aryl acid derivatives
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, (2008/06/13)
The use of diaryl acid derivatives of formula (I) or pharmaceutically acceptable salts, N-oxides, hydrates or solvates thereof, wherein the variables shown are defined in the disclosure, and their pharmaceutical compositions as PPAR ligand receptor binders. The PPAR ligand receptor binders of this invention are useful as agonists or antagonists of the PPAR receptor.
