149384-09-8Relevant academic research and scientific papers
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.
A step-economical route to fused 1,2,3-triazoles via an intramolecular 1,3-dipolar cycloaddition between a nitrile and an in situ generated aryldiazomethane
Mani, Neelakandha S.,Fitzgerald, Anne E.
, p. 8889 - 8894 (2015/01/08)
An intramolecular 1,3-dipolar cycloaddition strategy for rapid entry into triazole-fused heterocyclic compounds without recourse to the traditional Cu(1)-catalyzed azide-alkyne cycloadditions is described. Central to the strategy is the in situ generation of substituted diazomethanes in a two-step sequence from the corresponding aldehydes, which then undergo smooth cycloaddition with a cyano group to generate the desired fused 1,2,3-triazoles in good overall yields. The entire sequence can be carried out in a onepot operation.
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%).
Thiazolylbenzofuran derivatives and pharmaceutical composition comprising the same
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, (2008/06/13)
Compounds of the formula: STR1 wherein R1, R2, R3, R4, A, X and Y are as defined and pharmaceutically acceptable salts thereof; which have activities as leukotriene and Slow Reacting Substance of Anaphalaxis (SR
