147463-98-7Relevant academic research and scientific papers
P -TsOH-promoted synthesis of (E)-6-phenyl-7-styryl-5,6-dihydrodibenzo [b, h] [1,6]naphthyridines via cascade intramolecular aza-Michael addition/Friedlander condensation of 2′-aminochalcones in a SDS/H2O system
Ravi, Makthala,Chauhan, Parul,Singh, Shikha,Kant, Ruchir,Yadav, Prem. P.
, p. 48774 - 48778 (2016)
Br?nsted acid-promoted cascade synthesis of novel (E)-6-phenyl-7-styryl-5,6-dihydrodibenzo[b,h][1,6]naphthyridines has been achieved via homodimerization of 2′-aminochalcones by employing sodium dodecylsulphate (SDS) as a surfactant in water. Besides water as an environmentally benign reaction medium, the reaction proceeds smoothly with high atom-economy under a sequential one-pot protocol.
Organometallic titanocene complex as highly efficient bifunctional catalyst for intramolecular Mannich reaction
Wang, Yunyun,Jian, Yajun,Wu, Ya,Sun, Huaming,Zhang, Guofang,Zhang, Weiqiang,Gao, Ziwei
, (2019/05/07)
Bifunctional catalysts bearing two catalytic sites, Lewis acidic organometallic titanocene and Br?nsted acidic COOH, have been assembled in situ from Cp2TiCl2 with carboxylic acid ligands, showing high catalytic activity over an intramolecular Mannich reaction towards synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. The determination of the bifunctional catalyst Cp2Ti(C8H4NO6)2 was elucidated by single X-ray HR-MS and investigation of catalytic behavior. In particular, masking the Br?nsted acidic COOH catalytic site with dormant COOMe lowered the reaction yield greatly, indicating that two catalytic sites work together to maintain high catalytic efficiency.
2-aryl-2,3-dihydro-4(1H)-quinolinone semicarbazone compound and application thereof
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Paragraph 0071; 0072; 0073; 0074; 0075; 0076, (2018/10/19)
The invention relates to the field of medicine technology, and a series of novel 2-aryl-2,3-dihydrogen-4(1H)-quinolinone semicarbazone derivatives (I) and pharmaceutically acceptable salts, solvates,optical isomers or polymorphs are designed and synthesized. The derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph can be mixed as an active ingredient witha pharmaceutically acceptable carrier to prepare a pharmaceutical composition. A double dilution method is used for test of the antifungal activity of the derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph, and the results show that the derivative has stronger killing effect on clinically common pathogenic fungi, and is expected to overcome the defects oflarge toxic and side effects, easy generation of drug resistance of azole antifungal medicines which are widely used clinically. The specific formula is shown in the description.
Zirconyl Nitrate as an Efficient Catalyst for Facile Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1 H)-one Derivatives in Aqueous Medium
Gorepatil, Amarsinha,Gorepatil, Pratapsinha,Gaikwad, Mahadev,Mhamane, Dattakumar,Phadkule, Ajit,Ingle, Vilas
, p. 235 - 237 (2017/09/28)
A simple, green, and efficient method is introduced for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1 H)-ones under mild reaction conditions with improved yields by intramolecular cyclization of o -aminochalcones with zirconyl nitrate [Zn(O)(NO 3/
Silica-gel-supported Ce(SO4)2·4H2O-mediated cyclization of 2′-amino and 2′-hydroxychalcones under solvent-free conditions
Liu, Ruihuan,Zhang, Yan,Xu, Kangping,Tan, Guishan
supporting information, p. 1 - 9 (2016/12/30)
A simple, efficient, and environmentally friendly approach for the synthesis of flavones, aza-flavones, and aza-flavanones from corresponding 2′-hydroxy or 2′-aminochalcones has been developed. The reactions are successfully conducted in presence of silica-gel-supported Ce(SO4)2·4H2O under solvent-free conditions.
[C8dabco]Br: a mild and convenient catalyst for intramolecular cyclization of 2-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones
Derabli, Chamseddine,Mahdjoub, Sara,Boulcina, Raouf,Boumoud, Boudjemaa,Merazig, Hocine,Debache, Abdelmadjid
, p. 99 - 103 (2016/07/06)
[Figure not available: see fulltext.] A new and convenient synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been described using the intramolecular cyclization of 2-aminochalcones catalyzed by 1-octyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide ([Cs
A general and efficient synthesis of 5,6-dihydrodibenzo[b,h][1,6]naphthyridine derivatives
Dobrowolski, Jeremy C.,Katen, Alice,Fraser, Benjamin H.,Bhadbhade, Mohan,Black, David StC.,Kumar, Naresh
, p. 5442 - 5445 (2016/11/19)
A two-step procedure for the synthesis of dihydrodibenzonaphthyridine derivatives from benzaldehydes and 2-aminoacetophenones, proceeding through a substituted dihydroquinolone intermediate, is described. The synthetic protocol allows for a versatile and robust coupling method between a range of 2-aminoacetophenones or 2-aminobenzophenones and a selection of substituted dihydroquinolones.
Use of Mesoporous Molecular Sieves in the Production of Fine Chemicals: Preparation of Dihydroquinolinones of Pharmaceutical Interest from 2′-Aminochalcones
Climent, María J.,Corma, Avelino,Iborra, Sara,Martí, Laura
, p. 1335 - 1345 (2016/04/20)
Solid catalysts can be an alternative to homogeneous mineral Br?nsted and Lewis acids for the synthesis of pharmaceuticals provided that the diffusional and adsorption properties of the reactants and products can be controlled. Structured micro and especi
Mild and Efficient Silver(I) Triflate Catalyzed Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1 H)-ones, and Their Antioxidant Activities
Pandit, Rameshwar Prasad,Sharma, Kavita,Lee, Yong Rok
, p. 3881 - 3890 (2015/12/18)
Biologically interesting 2-aryl-2,3-dihydroquinolin-4(1H)-ones were synthesized using a mild and efficient one-pot procedure starting from o-aminoacetophenones and aromatic aldehydes in the presence of silver(I) triflate. This synthetic protocol provides rapid access to a variety of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. This technique has several advantages, such as the use of easily available starting materials, the efficiency of the catalyst, a simple operation, and tolerance of a wide range of functionality in the aldehydes. Screening of the synthesized compounds for their antioxidant properties revealed that two compounds (with EC50 = 15.42 μM and 15.16 μM) exhibit a potent free-radical scavenging ability towards TEAC free radicals compared to the standard, Trolox.
Design and synthesis of aza-flavones as a new class of xanthine oxidase inhibitors
Dhiman, Rajni,Sharma, Sahil,Singh, Gagandip,Nepali, Kunal,Singh Bedi, Preet Mohinder
, p. 7 - 16 (2013/02/23)
In an attempt to develop non-purine-based xanthine oxidase (XO) inhibitors, keeping in view the complications reported with the use of purine-based XO inhibitors, the flavone framework (a class possessing XO inhibitory potential) was used as lead structure for further optimization. By means of structure-based classical bioisosterism, quinolone was used as an isoster for chromone (a bicyclic unit present in flavones), owing to the bioactive potential and drug-like properties of quinolones. This type of replacement does not alter the shape and structural features required for XO inhibition, and also provides some additional interaction sites, without the loss of hydrogen bonding and hydrophobic and arene-arene interactions. In the present study, a series of 2-aryl/heteroaryl-4-quinolones (aza analogs of flavones) was rationally designed, synthesized and evaluated for in vitro XO inhibitory activity. Some notions about structure-activity relationships are presented indicating the influence of the nature of the 2-aryl ring on the inhibitory activity. Important interactions of the most active compound 3l (IC50 = 6.24 μM) with the amino acid residues of the active site of XO were figured out by molecular modeling. To develop non-purine-based xanthine oxidase inhibitors, the flavone framework was used as lead structure for further optimization. By means of structure-based classical bioisosterism, quinolone was used as an isoster for chromone. This type of replacement does not alter the shape and structural features required for xanthine oxidase inhibition. The rationally designed and synthesized series of 2-aryl/heteroaryl-4-quinolones (aza analogs of flavones) was evaluated for in vitro xanthine oxidase inhibitory activity. Copyright
