14959-64-9

Upstream product

• 62303-05-3 2-iodo-N-(p-tolyl)benzamide 
• 536-74-3 phenylacetylene 
• 13141-40-7 [2-(2-phenylethynyl)phenyl]methanol 
• 100-52-7 benzaldehyde 
• 106-49-0 p-toluidine 
• 2272-45-9 benzal-p-toluidine 
• 873-32-5 2-Chlorobenzonitrile 
• 23564-83-2 2-chloro-N-(p-tolyl)benzimidamide 
• 29539-19-3 (Z)?1?benzylidene?1,3?dihydroisobenzofuran 
• 19562-37-9 3-(4-methylphenyl)benzo-1,2,3-triazin-4(3H)-one 
• 591-50-4 iodobenzene 
• 1040256-02-7 C₂₂H₂₄BNO₃ 

Relevant academic research and scientific papers

Sonochemical synthesis of rosuvastatin based novel 3-methyleneisoindolin-1-one derivatives as potential anticancer agents

The Sonochemical synthesis of a library of 3-methyleneisoindolin-1-one based novel small molecules derived from rosuvastatin designed as potential anticancer agents was undertaken. A Cu-mediated coupling-cyclization strategy was employed to prepare this new class of compounds in a single pot with notable regioselectivity. The use of a terminal alkyne containing the propargylic ether moiety seemed to be responsible for the observed regioselectivity. Evaluation of all these compounds against three cancer cell lines e.g. HCT 116, HepG2 and PA-1 and a non-cancerous HEK cell line resulted in the identification of compound 3b as a promising cytotoxic agent with IC50 of 3.34 ± 0.38 and 1.16 ± 0.20 μM against HCT 116 and PA-1, respectively. In another study 3b showed significant decrease in p-Akt substrates (western blot analysis) indicating its ability to inhibit the p-Akt signal transduction pathway and arresting the growth of PANC-1 cells in vitro. Indeed, 3b showed better cytotoxic effect on PANC-1 cells over rosuvastatin (MTT assay). Notably, the lack of any significant effect of 3b on non-cancerous HEK cell line suggested its potential selectivity towards cancer cells. Further, a reasonable ADME (in silico) was predicted for 3b that showed acceptable stability against rat liver microsomes in vitro. The compound also showed acceptable NOAEL (No Observed Adverse Effect Level ~ 100 μM) for teratogenicity and cardiotoxicity when evaluated for toxicities in Zebrafish embryo. Finally, unlike rosuvastatin the compound 3b did not show any lipid lowering effects in Zebrafish larvae. Overall, as a novel and promising but safer cytotoxic agent 3b could be useful for the potential treatment of colorectal / ovarian and pancreatic cancer.

Nickel-Catalyzed Annulation of o-Haloarylamidines with Aryl Acetylenes: Synthesis of Isoquinolone and 1-Aminoisoquinoline Derivatives

An efficient method for the synthesis of substituted 1(2H)-isoquinolone derivatives via nickel-catalyzed annulation of substituted 2-halobenzamidines with aryl alkynes in the presence of water is described. Benzo[4,5]imidazo[2,1-a]isoquinolines were formed as the dominated products when dry dimethyl sulfoxide was used as the solvent. Furthermore, when benzyl substituted amidines were used as the substrates, debenzylation reaction occured to provide various 1-aminoisoquinoline products. (Figure presented.).

Mild and efficient synthesis of indoles and isoquinolones via a nickel-catalyzed Larock-type heteroannulation reaction

A simple and efficient approach for the preparation of substituted indoles and isoquinolones via a nickel-catalyzed Larock-type heteroannulation reaction is reported. This transformation employed air-stable and inexpensive Ni(dppp)Cl2 as a precatalyst and Et3N as a mild base. Moreover, the reaction occurs efficiently under mild conditions, and a wide range of substituted indoles and isoquinolones bearing various functional groups are obtained in moderate to excellent yields.

Construction of isoquinolin-1(2H)-ones by copper-catalyzed tandem reactions of 2-(1-Alkynyl)benzaldimines with water

The Cu(OAc)2-catalyzed tandem reaction of 2-(1-alkynyl)benzaldimines with water for the synthesis of isoquinolin-1(2H)-ones was developed. Moreover, 4-halogen-substituted isoquinolin-1(2H)-ones were obtained in good yields simply by including N-halosuccinimides (NXS: X = Cl, Br, I) in the reaction system. Mechanistic studies indicated that the reactions are probably initiated by highly regioselective intramolecular cyclization of 2-(1-alkynyl)benzaldimines to give the corresponding isoquinolinium intermediates. The Cu(OAc)2-catalyzed tandem reaction of 2-(1-alkynyl)benzaldimines with water for the synthesis of isoquinolin-1(2H)-ones is developed. 4-Halogen-substituted isoquinolin-1(2H)-ones can be obtained in good yields simply by including N-halosuccinimides (NXS) in the reaction system. Mechanistic studies are also undertaken.

Transition metal-free cascade reactions of alkynols to afford isoquinolin-1(2H)-one and dihydroisobenzofuran derivatives

Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.

Solvent-switched benzylic methylene functionalization: Addition, ring-opening, cyclization, and unexpected cleavage of C-O and C-C bonds

Intermolecular benzylic methylene functionalization of exo-cyclic enol ethers has been achieved using imines as reagents and potassium tert-butoxide as the catalyst. Depending on the solvent used, the reaction proceeds by two pathways. In THF, an addition

Synthesis of highly substituted isoquinolone derivatives by nickel-catalyzed annulation of 2-halobenzamides with alkynes

(Equation Presented). An efficient method for the synthesis of substituted 1(2H)-isoquinolone derivatives via nickel-catalyzed annulation of substituted 2-halobenzamides with alkynes is described. This protocol is successfully applied to the total synthes

Synthesis of 1(2H)-isoquinolones by the nickel-catalyzed denitrogenative alkyne insertion of 1,2,3-benzotriazin-4(3H)-ones

(Chemical Equation Presented) 1,2,3-Benzotriazin-4(3H)-ones reacted with internal and terminal alkynes in the presence of a nickel(0)/phosphine catalyst to give a wide range of substituted 1(2H)-isoquinolones in high yield. The reaction proceeded through denitrogenative activation of the triazinone moiety and the following insertion of alkynes.