60798-13-2Relevant academic research and scientific papers
Synthesis of Tetrasubstituted Pyrazoles from Substituted Hydrazines and β-Keto Esters
Bakanas, Ian J.,Moura-Letts, Gustavo
, p. 5345 - 5349 (2016)
Herein we report the synthesis of tetrasubstituted pyrazoles from simple hydrazines and β-keto esters under mild, basic conditions. This reaction enables the selective synthesis of pyrazolones, alkoxypyrazoles, and tetrasubstituted pyrazoles for a large v
Palladium catalysed hydrolysis-free arylation of aliphatic nitriles for the synthesis of 4-arylquinolin-2-one/pyrazolone derivatives
Krishna Reddy, Singarajanahalli Mundarinti,Prasanna Kumari, Subramaniyan,Selva Ganesan, Subramaniapillai
, (2021/08/03)
Palladium catalysed addition of arylboronic acid to the readily available 2-cyano-(N-aryl)-acetamide or ethyl-2-cyanoacetate followed by subsequent reaction transform them into the biologically significant 4-arylquinolin-2-one or pyrazolone derivatives. The reaction conditions are robust enough to prevent the hydrolysis of ester/amide moiety during arylation. In addition, the unactivated nitrile moiety in the acetonitrile also converted to the corresponding acetophenone derivative.
Targeting fungal virulence factor by small molecules: Structure-based discovery of novel secreted aspartic protease 2 (SAP2) inhibitors
Dong, Guoqiang,Han, Guiyan,Li, Chenglan,Liu, Na,Liu, Yang,Sheng, Chunquan,Tu, Jie,Wu, Shanchao
supporting information, (2020/07/06)
Secreted aspartic protease 2 (SAP2), a kind of virulence factor, is an emerging new antifungal target. Using docking-based virtual screening and structure-based inhibitor design, a series of novel SAP2 inhibitors were successfully identified. Among them, indolone derivative 24a showed potent SAP2 inhibitory activity (IC50 = 0.92 μM). It blocked fungi biofilm and hypha formation by down-regulating the expression of genes SAP2, ECE1, ALS3 and EFG1. As a virulence factor inhibitor, compound 24a was inactive in vitro and showed potent in vivo efficacy in a murine model of invasive candidiasis. It represents a promising lead compound for the discovery of novel antifungal agents.
Asymmetric synthesis of atropisomeric pyrazole: Via an enantioselective reaction of azonaphthalene with pyrazolone
Yuan, Huijun,Li, Yao,Zhao, Hanhui,Yang, Zhihong,Li, Xin,Li, Wenjun
supporting information, p. 12715 - 12718 (2019/10/28)
The first catalytic asymmetric reaction of azonaphthalene with pyrazolone has been established. A wide range of axially chiral pyrazole derivatives have been achieved in good yields (68-99%) with excellent enantioselectivities (83-98% ee) by utilizing chiral phosphoric acid as a catalyst. This strategy provides an efficient and facile approach for the construction of axially chiral pyrazole derivatives. Theoretical calculations were carried out to elucidate the origins of enantioselectivity.
Asymmetric [3 + 3] Annulation of Copper-Allenylidenes with Pyrazolones: Synthesis of Chiral 1,4-Dihydropyrano[2,3- c]pyrazoles
Jiang, Feng,Feng, Xinping,Wang, Rou,Gao, Xing,Jia, Hao,Xiao, Yumei,Zhang, Cheng,Guo, Hongchao
supporting information, p. 5278 - 5281 (2018/09/13)
The copper-catalyzed asymmetric [3 + 3] annulation of ethynyl benzoxazinanones with pyrazolones has been achieved, providing simple access to 1,4-dihydropyrano[2,3-c]pyrazole derivatives in moderate to excellent yields with excellent enantioselectivities (up to 99% ee). Compared with previous annulation reactions of copper-allenylidenes from ethynyl benzoxazinanones, the current reaction fused the three carbon atoms of the propargyl moiety into a heterocyclic framework.
One-pot multistep mechanochemical synthesis of fluorinated pyrazolones
Howard, Joseph L.,Nicholson, William,Sagatov, Yerbol,Browne, Duncan L.
supporting information, p. 1950 - 1956 (2017/09/27)
Solventless mechanochemical synthesis represents a technique with improved sustainability metrics compared to solvent-based processes. Herein, we describe a methodical process to run one solventless reaction directly into another through multistep mechanochemistry, effectively amplifying the solvent savings. The approach has to consider the solid form of the materials and compatibility of any auxiliary used. This has culminated in the development of a two-step, one-jar protocol for heterocycle formation and subsequent fluorination that has been successfully applied across a range of substrates, resulting in 12 difluorinated pyrazolones in moderate to excellent yields.
Pyrazolone derivatives: Synthesis, anti-inflammatory, analgesic quantitative structure-activity relationship and in vitro studies
Ragab, Fatma Abdel-Fattah,Abdel-Gawad, Nagwa Mohamed,Georgey, Hanan Hanna,Said, Mona Fikry
, p. 834 - 845 (2013/09/12)
Some 1-(4-chlorophenyl or benzenesulfonamide)-2,3- and/or 4-substituted-1H-pyrazol-5(4H)-one derivatives were synthesized and screened for their anti-inflammatory and analgesic activities, in addition to their ulcerogenic liability. They were found to be active as anti-inflammatory and analgesic agents. Compound 6b was found to be the most active as anti-inflammatory agent and compound 9b was found to be the most active one as anti-inflammatory and analgesic agent. On the other hand, cyclooxygenase-1/-2 (COX-1)/COX-2 isozyme selectivity was also done and the tested compounds showed equal inhibition to both isoforms. Moreover, 2D-quantitative structure-activity relationship (QSAR) studies revealed well predictive and statistically significant and cross validated QSAR model that helps to explore some expectedly potent compounds.
Synthesis, crystal structure and evaluation of cancer inhibitory activity of 4-[indol-3-yl-methylene]-1H-pyrazol-5(4H)-one derivatives
Jing, Lingling,Wang, Liang,Zhao, Yinglan,Tan, Rui,Xing, Xiumei,Liu, Ting,Huang, Wencai,Luo, Youfu,Li, Zicheng
, p. 691 - 696 (2013/02/23)
A series of 4-(1H-indol-3-yl-methylene)-1H-pyrazol-5(4H)-one derivatives have been synthesised. The Z structure of 4-[(1-methyl-1H-indol-3-yl)methylene]- 3-phenyl-1-p-tolyl-1H-pyrazol-5-one was determined by X-ray crystallography. The antitumour activity was evaluated against five cancer cells by MTT assay. [(1H-Indol-3-yl)methylene]-1-(2,4-dinitrophenyl)- 3-methyl-1H-pyrazole-5-one and 4-{4-[(1-benzyl-1H-indol-3-yl)methylene]-3-methyl-5-oxo-4,5-dihydro-1Hpyrazol- 1-yl}-benzoic acid have similar anticancer activity with 5-UF on the test cancer cells (exception of A375). Almost all the target compounds displayed antitumour activity against A549 and PC-9, and those with benzyl at 1- position of indole had higher activity against PC-9 (IC50 value lower than 30 μM). Those with benzyl at the indole and carboxyl at the phenyl part of of pyrazole were more active against PC-9 and A549 cells, providing a good indication for subsequent optimisation as lung cancer inhibitory agents.
Synthesis and evaluation of pyrazolone compounds as SARS-coronavirus 3C-like protease inhibitors
Ramajayam,Tan, Kian-Pin,Liu, Hun-Ge,Liang, Po-Huang
experimental part, p. 7849 - 7854 (2011/02/23)
A series of pyrazolone compounds as possible SARS-CoV 3CL protease inhibitors were designed, synthesized, and evaluated by in vitro protease assay using fluorogenic substrate peptide in which several showed potent inhibition against the 3CL protease. Interestingly, one of the inhibitors was also active against 3C protease from coxsackievirus B3. These inhibitors could be potentially developed into anti-coronaviral and anti-picornaviral agents.
Synthesis, biological evaluation and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis
Castagnolo, Daniele,De Logu, Alessandro,Radi, Marco,Bechi, Beatrice,Manetti, Fabrizio,Magnani, Matteo,Supino, Sibilla,Meleddu, Rita,Chisu, Lorenza,Botta, Maurizio
, p. 8587 - 8591 (2008/12/23)
As a continuation of our previous work that turned toward the identification of antimycobacterial compounds with innovative structures, two series of pyrazole derivatives were synthesized by parallel solution-phase synthesis and were assayed as inhibitors of Mycobacterium tuberculosis (MTB), which is the causative agent of tuberculosis. One of these compounds showed high activity against MTB (MIC = 4 μg/mL). The newly synthesized pyrazoles were also computationally investigated to analyze their fit properties to the pharmacophoric model for antitubercular compounds previously built by us and to refine structure-activity relationship analysis.
