2515-62-0Relevant articles and documents
Asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives: Which possesses the highest activity to protect DNA or scavenge radical?
Li, Pei-Ze,Liu, Zai-Qun
, p. 3478 - 3490 (2014)
A series of asymmetrical mono-carbonyl ferrocenylidene curcumin and their dihydropyrazole derivatives were synthesized. Their antioxidant abilities in protecting DNA against 2,2′-azobis(2-amidinopropane hydrochloride)-induced oxidation and scavenging 2,2′-azinobis(3-ethylbenzothiazoline-6- sulfonate) cationic radical (ABTS) radical were evaluated. In synthesis, the Michael addition reactions between phenylhydrazine and asymmetrical ferrocenylidene curcumin derivatives exhibit evident regioselectivity. The direction of addition depends on whether the benzene ring is substituted or not. The antioxidant abilities of compounds will increase when the ferrocenyl group is introduced. Moreover, such improvement derived from ferrocenyl group is also related to other substituent groups in molecule, not independent. Interestingly, p-dimethylamino group which is never considered as an active group, however, exhibits the best activity in protecting DNA and scavenging ABTS radical.
Second harmonic generation in pyrazoline derivatives of dibenzylideneacetones and chalcone: A combined experimental and theoretical approach
de Araújo, Raiane Sodré,de Alcantara, Aline Moreira,Abeg?o, Luis M.G.,de Souza, Yago Pereira,Brand?o Silva, Ant?nio Carlos,Machado, Rogério,Joatan Rodrigues, José,Rodriguez Pliego, Josefredo,d'Errico, Francesco,Siqueira Valle, Marcelo,de Alencar, Márcio André Rodrigues Cavalcanti
, (2019/11/13)
In this work, we investigate theoretically and experimentally second harmonic generation (SHG) in three pyrazoline compounds, being two derivatives of dibenzylideneacetone (DBA) (C23H20N2 and C25H24N2O2) and one derivative of chalcone (C21H18N2). The compounds were synthesized after two steps employing a Claisen-Schmidt condensation followed by an addition-elimination reaction with phenylhydrazine. All compounds were characterized using NMR, FT-IR, UV-Vis, and XRD. We calculated the first-order hyperpolarizabilities of these molecules using program packages based on the time-dependent Hartree-Fock (TDHF) and density functional theory (DFT). SHG was characterized by Kurtz and Perry's powder method. We observed that these organic crystals present SHG efficiencies up to 5 times larger than the KDP, and we associated these values to their molecular structure and crystalline arrangements. The values obtained experimentally and theoretically evidence that these compounds have good potential for application in electronic devices based on second-order nonlinear responses.
Direct N-heterocyclization of hydrazines to access styrylated pyrazoles: synthesis of 1,3,5-trisubstituted pyrazoles and dihydropyrazoles
Venkateswarlu, Vunnam,Kour, Jaspreet,Kumar, K. A. Aravinda,Verma, Praveen Kumar,Reddy, G. Lakshma,Hussain, Yaseen,Tabassum, Aliya,Balgotra, Shilpi,Gupta, Sorav,Hudwekar, Abhinandan D.,Vishwakarma, Ram A.,Sawant, Sanghapal D.
, p. 26523 - 26527 (2018/08/07)
A microwave-assisted method has been developed for the synthesis of tri-substituted pyrazoles via direct N-heterocyclization of hydrazines with metal-acetylacetonate and -dibenzylideneacetonate without using any base or additives. Most importantly, the synthesis of 1-aryl-5-phenyl-3-styryl-1H-pyrazoles was achieved in a single step using hydrochloride salt of various phenylhydrazines and this is the first report for direct construction of these molecules. The reaction medium and microwave conditions play a critical role for their selective product formation during the reaction. The present reaction explored the usage of metal-diketonic complexes as reaction substrates providing acetylacetone and dibenzylideneacetone moieties to directly participate in cyclization with hydrazines to form the corresponding pyrazoles in excellent yields. The present protocol introduces the important N-heterocyclic moieties in the final structures, giving the reaction great applications from a medicinal chemistry perspective, particularly in the late stage modification strategies in drug discovery.
