57221-66-6

Upstream product

• 552-16-9 ortho-nitrobenzoic acid 
• 6315-96-4 1-(2-naphthyl)-1-propanone 
• 552-89-6 2-nitro-benzaldehyde 
• 93-08-3 methyl 2-naphthyl ketone 
• 1777-59-9 1-(naphthalen-2-yl)-2-(triphenylphosphoranylidene)ethanone 

Downstream Products

• 1346745-13-8 1-[4,5-dihydro-3-(naphth-2-yl)-5-(2-nitrophenyl)-1H-pyrazol-1-yl]ethanone 
• 1451011-95-2 C₁₉H₁₅NO 

Relevant academic research and scientific papers

Design, synthesis, biological evaluation of 3,5-diaryl-4,5-dihydro-1H-pyrazole carbaldehydes as non-purine xanthine oxidase inhibitors: Tracing the anticancer mechanism via xanthine oxidase inhibition

Xanthine oxidase (XO) has been primarily targeted for the development of anti-hyperuriciemic /anti-gout agents as it catalyzes the conversion of xanthine and hypoxanthine into uric acid. XO overexpression in various cancer is very well correlated due to r

Synthesis of 1,4-dihydropyrazolo[4,3-b]indoles via intramolecular C(sp2)-N bond formation involving nitrene insertion, DFT study and their anticancer assessment

We herein report a new synthetic route for a series of unreported 1,4-dihydropyrazolo[4,3-b]indoles (6–8) via deoxygenation of o-nitrophenyl-substituted N-aryl pyrazoles and subsequent intramolecular (sp2)-N bond formation under microwave irradiation expedite modified Cadogan condition. This method allows access to NH-free as well as N-substituted fused indoles. DFT study and controlled experiments highlighted the role of nitrene insertion as one of the plausible reaction mechanisms. Furthermore, the target compounds exhibited cytotoxicity at low micromolar concentration against lung (A549), colon (HCT-116), and breast (MDA-MB-231, and MCF-7) cancer cell lines, induced the ROS generation and altered the mitochondrial membrane potential of highly aggressive MDA-MB-231 cells. Further investigations revealed that these compounds were selective Topo I (6h) or Topo II (7a, 7b) inhibitors.

Enantioselective Synthesis of Tetrahydroquinolines via One-Pot Cascade Biomimetic Reduction?

A novel and efficient protocol for the synthesis of chiral tetrahydroquinoline derivatives with excellent enantioselectivities and high yields has been developed through one-pot cascade biomimetic reduction. The detailed reaction pathway includes the acid-catalyzed and ruthenium-catalyzed formation of aromatic quinoline intermediates and biomimetic asymmetric reduction.

Visible-Light Induction/Br?nsted Acid Catalysis in Relay for the Enantioselective Synthesis of Tetrahydroquinolines

An efficient method merging Br?nsted acid catalysis with visible-light induction for the highly enantioselective synthesis of tetrahydroquinolines has been developed. This mild process directly transforms 2-aminoenones into 2-substituted tetrahydroquinolines with excellent enantioselectivities through a relay visible-light-induced cyclization/chiral phosphoric acid-catalyzed transfer hydrogenation reaction.

Organocatalyzed aerobic oxidative Robinson-type annulation of 2-isocyanochalcones: expedient synthesis of phenanthridines

A DBU-catalyzed aerobic oxidative Robinson annulation of 2-isocyanochalcones with active methylene ketones was developed for the expedient synthesis of phenanthridines in high to excellent yields. This unprecedented multistep domino reaction represents a

Redox-Neutral Access to Sultams from 2-Nitrochalcones and Sulfur with Complete Atom Economy

A catalyst-free, redox-neutral, and completely atom-economical synthesis of sultams by simply heating 2-nitrochalcones with elemental sulfur in 3-picoline or N-methylmorpholine is described. The S-N, C-S, and S=O bonds of the sulfonamide are efficiently f

Asymmetric synthesis of CF3-containing tetrahydroquinoline: Via a thiourea-catalyzed cascade reaction

An organocatalytic asymmetric method for the synthesis of 2-CF3 tetrahydroquinoline has been achieved. The cascade reaction of 2-aminochalcones with β-CF3 nitroalkenes afforded the products bearing three contiguous stereogenic centers in good yields with excellent diastereoselectivities and enantioselectivities.

Pd-catalyzed cross-coupling of aryl carboxylic acids with propiophenones through a combination of decarboxylation and dehydrogenation

A palladium-catalyzed cross-coupling reaction of aryl carboxylic acids with saturated propiophenones through a combination of decarboxylation and dehydrogenation to form Heck-type products was reported. In a glove box, a 25 mL tube equipped with a stir bar was charged with Pd(OAc)2, PCy3, propiophenone, 2-nitrobenzoic acid, Ag2CO3 and nBu4NOAc HOAc. Then, the mixture was heated under nitrogen at 90°C in DMF for 24 h. After cooling down, the crude reaction mixture was analyzed by GC with n-dodecane as an internal standard to obtain 3a in 75% GC yield. Relatively weak bases, such as carboxylate salts, facilitated this reaction and the effect of the bases was a function of their solubility, while strong bases, such as K3PO4 and K2CO3 shut down the reaction completely. The simultaneous use of carboxylate salts and equimolar carboxylic acids significantly improved the yield of 3a, although the use of acetic acid alone was ineffective for the reaction.

Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones

Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C6-C 3-C6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Springer Science+Business Media, LLC 2011.