1611-84-3Relevant academic research and scientific papers
Reductive Ring-Opening 1,3-Difunctionalizations of Arylcyclopropanes with Sodium Metal
Wang, Shuo,Kaga, Atsushi,Yorimitsu, Hideki
supporting information, p. 219 - 223 (2020/11/04)
Sodium dispersion promotes reductive ring opening of arylcyclopropanes. The presence of a reduction-resistant electrophile, such as methoxypinacolatoborane, epoxide, oxetane, paraformaldehyde, or chlorotrimethylsilane, during the reductive ring opening event leads to the formation of 1,3-difunctionalized 1-arylalkanes by immediate trappings of the resulting two reactive carbanions. In particular, the ring-opening 1,3-diborylations of arylcyclopropanes afford 1,3-diborylalkanes with high syn selectivity.
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.
Preparation, Antiepileptic Activity, and Cardiovascular Safety of Dihydropyrazoles as Brain-Penetrant T-Type Calcium Channel Blockers
Remen, Lubos,Bezen?on, Olivier,Simons, Lloyd,Gaston, Rick,Downing, Dennis,Gatfield, John,Roch, Catherine,Kessler, Melanie,Mosbacher, Johannes,Pfeifer, Thomas,Grisostomi, Corinna,Rey, Markus,Ertel, Eric A.,Moon, Richard
supporting information, p. 8398 - 8411 (2016/10/03)
A series of dihydropyrazole derivatives was developed as potent, selective, and brain-penetrating T-type calcium channel blockers. An optimized derivative, compound 6c, was advanced to in vivo studies, where it demonstrated efficacy in the WAG/Rij rat model of generalized nonconvulsive, absence-like epilepsy. Compound 6c was not efficacious in the basolateral amygdala kindling rat model of temporal lobe epilepsy, and it led to prolongation of the PR interval in ECG recordings in rodents.
Synthesis and evaluation of human monoamine oxidase inhibitory activities of some 3,5-diaryl-N-substituted-4,5-dihydro-1H-pyrazole-1-carbothioamide derivatives
Sentuerk, Kerem,Tan, Oya Unsal,Ciftci, Samiye Yabanoglu,Ucar, Guelberk,Palaska, Erhan
, p. 695 - 702 (2012/11/07)
Sixteen 3-aryl-5-(4-fluorophenyl)-N-substituted-4,5-dihydro-1H-pyrazole-1- carbothioamide derivatives were synthesized and their structure were identified by UV, IR, 1H NMR, mass spectra, and microanalyses. The compounds were evaluated in vitro for their human monoamine oxidase (hMAO) inhibitory activities and their MAO-A and -B selectivity. All the compounds were found to potently inhibit MAO-A isoforms. 5-(4-Fluorophenyl)-3-(4-methoxyphenyl)-N- methyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (1.0 × 10-3 μM) was found to inhibit hMAO-A most selectively and potently. The binding mode of 5-(4-fluorophenyl)-3-(4-methoxyphenyl)-N-methyl-4,5-dihydro-1H-pyrazole- 1-carbothioamide to hMAO-A was also predicted using docking studies.
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.
New 2-pyrazolines of anticipated molluscicidal activity
Mishriky,Asaad,Ibrahim,Girgis
, p. 544 - 548 (2007/10/03)
A facile one-pot synthesis of 1-substituted carbamoyl or thiocarbamoyl-2-pyrazolines 6 is described. Also, the synthesis as well as the molluscicidal activity of 1,3,5-triaryl- (2), 1-acetyl-3,5-diaryl- (4) 2-pyrazolines are outlined.
New 2-pyrazolines of anticipated molluscicidal activity
Mishriky, Nawal,Asaad, Fahmy M.,Ibrahim, Yehia A.,Girgis, Adel S.
, p. 935 - 940 (2007/10/03)
A facile one-pot synthesis of 1-substituted carbamoyl- or thiocarbamoyl-2-pyrazolines 6 is described. The synthesis as well as molluscicidal activity of 1,3,5-triaryl- and 1-acetyl-3,5-diaryl-2-pyrazolines (2 and 4) are also outlined.
