16619-60-6Relevant academic research and scientific papers
Synthesis of new pyrazoline-nucleoside analogue derivatives
Azouz,Lammara,Benallia,Guenane
, p. 294 - 305 (2013)
In this work, a synthesis of pyrazoline nucleosides analogues is presented, using the stereospecific sodium salt glycosylation procedure. In the first step, chalcones were prepared using Claisen Schmidt reaction by reacting benzaldehyde with enolizable ketones in ethanolic NaOH solutions. Next, these chalcones were immediately reacted with hydrazine hydrochloridein the presence of dry methanol to obtain the corresponding 2-pyrazolines. Finally, the coupling of the pyrazolines with 1-chloro-arabinofuranose leads to different β-nucleosides as the major product (13-17) in good yields. The structures of these derivatives were characterized by infrared and 1HNMR spectroscopy and mass spectrometry.
Synthesis and Biological Evaluation of Pyrazoline and Pyrrolidine-2,5-dione Hybrids as Potential Antitumor Agents
Anisimova, Natalia Y.,Choe, Jun-yong,Lavecchia, Antonio,Loiodice, Fulvio,Meyer-Almes, Franz-Josef,Pokrovsky, Vadim S.,S Ramaa, C.,Smirnova, Galina B.,Sokolova, Darina V.,Spirina, Tatiana S.,Tilekar, Kalpana,Upadhyay, Neha
, p. 1813 - 1825 (2020/09/07)
In search of novel and effective antitumor agents, pyrazoline-substituted pyrrolidine-2,5-dione hybrids were designed, synthesized and evaluated in silico, in vitro and in vivo for anticancer efficacy. All the compounds exhibited remarkable cytotoxic effects in MCF7 and HT29 cells. The excellent antiproliferative activity toward MCF7 (IC50=0.78±0.01 μM), HT29 (IC50=0.92±0.15 μM) and K562 (IC50=47.25±1.24 μM) cell lines, prompted us to further investigate the antitumor effects of the best compound S2 (1-(2-(3-(4-fluorophenyl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2,5-dione). In cell-cycle analysis, S2 was found to disrupt the growth phases with increased cell population in G1/G0 phase and decreased cell population in G2/M phase. The excellent in vitro effects were also supported by inhibition of anti-apoptotic protein Bcl-2. In vivo tumor regression studies of S2 in HT29 xenograft nude mice, exhibited equivalent and promising tumor regression with maximum TGI, 66 % (i. p. route) and 60 % (oral route) at 50 mg kg?1 dose by both the routes, indicating oral bioavailability and antitumor efficacy. These findings advocate that hybridization of pyrazoline and pyrrolidine-2,5-dioes holds promise for the development of more potent and less toxic anticancer agents.
Development of 5-(Aryl)-3-phenyl-1H-pyrazole Derivatives as Potent Antimicrobial Compounds
Nagendra Chowdary,Umashankara,Dinesh,Girish,Ramesha Baba
, p. 45 - 50 (2018/12/11)
A series of 16 chalcone compounds were synthesized by Claisen-Schmidt condensation of various aldehydes with acetophenone using KOH as a base in ethanol. The reaction affords the desired products in good yields. Then all the 16 compounds were converted into pyrazoles by treating with hydrazine hydrate in ethanol under reflux condition. Both chalcones and pyrazoles were screened for their in vitro antibacterial (Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa) and antifungal (Aspergillus flavus, Chrysosporium keratinophilum and Candida albicans) activity. Biological activities of these compounds were compared with those of commercially available antibiotic ampicillin and antifungal agent miconazole. Pyrazoles were found to be most active and effective than corresponding chalcones for antimicrobial activity. Out of the 7 pyrazole compounds tested for antibacterial and antifungal activity, 5 compounds, 4h, 4j, 4l, 4m and 4n are turned out to be potent antimicrobial agents. Therefore these derivatives could serve as a highly promising molecules for further development.
A class of novel tubulin polymerization inhibitors exert effective anti-tumor activity via mitotic catastrophe
Zhang, Ya-Liang,Li, Bo-Yan,Yang, Rong,Xia, Lin-Ying,Fan, A-Li,Chu, Yi-Chun,Wang, Lin-Jian,Wang, Zhong-Chang,Jiang, Ai-Qin,Zhu, Hai-Liang
, p. 896 - 910 (2019/01/04)
In current work, a class of novel 4,5-dihydro-1H-pyrazole-1-carboxylate derivatives (E01-E28) were designed, synthesized and evaluated. Among them, the most potent compound E24 exhibited comparable activity against a panel of cancer cells (GI50
Nano-TiO2: An efficient and reusable catalyst for the synthesis of 1,3,5-substituted pyrazoles
Akbari, Ali,Mirjalili, Bibi Fatemeh
, p. 119 - 123 (2016/07/15)
(Formula presented) A Nano-TiO2 is an efficient catalysis for the synthesis of 1,3,5-substituted pyrazoles via condensation of 1,3- diketones and hydrazines. Simple procedure, mild heating, solvent free, high yielding, and easy workup are some advantages of this protocol. The catalyst can be recovered easily and reused many times without significant loss in catalytic activity and selectivity.
Containing 1,4-benzodioxane structure of the pyrazoline derivatives and the preparation and use thereof
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Paragraph 0033-0035, (2016/12/01)
The invention relates to pyrazoline derivatives comprising a 1,4-benzodioxan structure. The derivatives are characterized in that the derivatives have a general formula as the following. R1, R3, and R3 in the formula are as the following. The pyrazoline d
One-pot synthesis of 3,5-diphenyl-1h-pyrazoles from chalcones and hydrazine under mechanochemical ball milling
Zhang, Ze,Tan, Ya-Jun,Wang, Chun-Shan,Wu, Hao-Hao
, p. 103 - 112 (2014/02/14)
A highly efficient and environmentally friendly method has been developed for facile synthesis of 3,5-diphenyl-1H-pyrazoles under mechanochemical ball-milling conditions. The advantages of short reaction time, high efficiency, no separation of in situ generated intermediate, using cheap sodium persulfate as the oxidant, together with very simple work-up procedure, make this one-pot and solvent-free protocol a green and powerful alternative to traditional methods for the synthesis of these kinds of compounds.
SOCl2 catalyzed cyclization of chalcones: Synthesis and spectral studies of some bio-potent 1H pyrazoles
Ranganathan, Kaliyaperumal,Suresh, Ramamoorthy,Vanangamudi, Ganesan,Thirumurthy, Kannan,Mayavel, Perumal,Thirunarayanan, Ganesamoorthy
, p. 271 - 288 (2014/06/24)
Some aryl-aryl 1H pyrazoles have been synthesised by cyclization of aryl chalcones and hydrazine hydrate in the presence of SOCl2. The yields of the pyrazoles are more than 85%. These pyrazoles are characterized by their physical con
SAR studies of differently functionalized chalcones based hydrazones and their cyclized derivatives as inhibitors of mammalian cathepsin B and cathepsin H
Raghav, Neera,Singh, Mamta
supporting information, p. 4233 - 4245 (2014/08/18)
Cathepsins have emerged as potential drug targets for melanoma therapy and engrossed attention of researchers for development and evaluation of cysteine cathepsin inhibitors as cancer therapeutics. In this direction, we have designed, synthesized, and ass
Design, modification and 3D QSAR studies of novel 2,3-dihydrobenzo[b][1,4] dioxin-containing 4,5-dihydro-1H-pyrazole derivatives as inhibitors of B-Raf kinase
Yang, Yu-Shun,Li, Qing-Shan,Sun, Shuai,Zhang, Yan-Bin,Wang, Xiao-Liang,Zhang, Fei,Tang, Jian-Feng,Zhu, Hai-Liang
, p. 6048 - 6058 (2012/11/07)
Two series of novel 2,3-dihydrobenzo[b][1,4]dioxin-containing 4,5-dihydro-1H-pyrazole derivatives C1-C15 and D1-D15 have been synthesized and evaluated for their B-Raf inhibitory and anti-proliferation activities. Compound C14 ((3-(4-bromophenyl)-5-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3- dihydrobenzo[b][1,4]dioxin-6-yl)methanone) showed the most potent biological activity against B-RafV600E (IC50 = 0.11 μM) and WM266.4 human melanoma cell line (GI50 = 0.58 μM), being comparable with the positive control Erlotinib and more potent than our previous best compound, while D10 ((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(5-(3- fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone) performed the best in the D series (IC50 = 1.70 μM; GI50 = 1.45 μM). The docking simulation was performed to analyze the probable binding models and poses and the QSAR model was built for reasonable design of B-Raf inhibitors in future. The introduction of 2,3-dihydrobenzo[b][1,4]dioxin structure reinforced the combination of our compounds and the receptor, resulting in progress of bioactivity.
