2075-45-8Relevant articles and documents
Lipase-catalyzed alcoholytic resolution of (R,S)-flurbiprofenyl azolides for preparation of (R)-NO-flurbiprofen ester prodrugs
Ciou, Jyun-Fen,Wang, Pei-Yun,Wu, An-Chi,Tsai, Shau-Wei
, p. 960 - 965 (2011)
A lipase-catalyzed alcoholysis of (R,S)-flurbiprofenyl azolide in anhydrous methyl tert-butyl ether (MTBE) has been developed for the preparation of (R)-flurbiprofenyl ester, (S)-flurbiprofenyl azolide and hence (S)-flurbiprofen. On the basis of enzyme en
Scalable 9-Step Synthesis of the Splicing Modulator NVS-SM2
Abou-Hamdan, Hussein,Désaubry, Laurent
, p. 2954 - 2958 (2018)
NVS-SM2, the first activator of pre-mRNA splicing, displays remarkable pharmacological in vivo activities in models of spinal muscular atrophy. Herein we describe an improved approach to the synthesis of this compound, which features a convenient introduction of sterically encumbered amine moiety onto a fluoropyridazine intermediate.
Synthesis method for synthesizing N-protected 3-bromopyrazole by one-pot method
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Paragraph 0019; 0022-0037, (2021/04/10)
The invention provides a synthesis method for synthesizing N-protected 3-bromopyrazole by one-pot method, which comprises the steps that pyrazole reacts with a bromination reagent to obtain 3-bromo-pyrazole, and then 3-bromo-pyrazole is subjected to 'one-pot' reaction and vinyl ether reaction to obtain N-protected 3-bromo-pyrazole. According to the preparation method, the post-treatment step required by the first step of the two-step process is omitted, and the industrial production efficiency is greatly improved.
Cytotoxic Ruthenium(II) Complexes of Pyrazolylbenzimidazole Ligands That Inhibit VEGFR2 Phosphorylation
Acharya, Moulinath,Chakraborty, Ayan,Chakraborty, Manas Pratim,Das, Rahul,Koley, Tuhin Subhra,Mukherjee, Arindam,Purkait, Kallol,Roy, Shantanu Saha,Roy, Souryadip
supporting information, p. 18379 - 18394 (2021/12/01)
Eight new ruthenium(II) complexes of N,N-chelating pyrazolylbenzimidazole ligands of the general formula [RuII(p-cym)(L)X]+ [where the ligand L is 2-(1H-pyrazol-1-yl)-1H-benzo[d]imidazole (L1) substituted at the 4 position of the pyrazole ring by Cl (L2), Br (L3), or I (L4) and X = Cl- and I-] were synthesized and characterized using various analytical techniques. Complexes 1 and 3 were also characterized by single-crystal X-ray crystallography, and they crystallized as a monoclinic crystal system in space groups P21/n and P21/c, respectively. The complexes display good solution stability at physiological pH 7.4. The iodido-coordinated pyrazolylbenzimidazole ruthenium(II) p-cymene complexes (2, 4, 6, and 8) are more resistant toward hydrolysis and have less tendency to form monoaquated complexes in comparison to their chlorido analogues (1, 3, 5, and 7). The halido-substituted 2-(1H-pyrazol-1-yl)-1H-benzo[d]imidazole ligands, designed as organic-directing molecules, inhibit vascular endothelial growth factor receptor 2 (VEGFR2) phosphorylation. In addition, the ruthenium(II) complexes display a potential to bind to DNA bases. The cytotoxicity profile of the complexes (IC50 ca. 9-12 μM for 4-8) against the triple-negative breast cancer cells (MDA-MB-231) show that most of the complexes are efficient. The lipophilicity and cellular accumulation data of the complexes show a good correlation with the cytotoxicity profile of 1-8. The representative complexes 3 and 7 demonstrate the capability of arresting the cell cycle in the G2/M phase and induce apoptosis. The inhibition of VEGFR2 phosphorylation with the representative ligands L2 and L4 and the corresponding metal complexes 3 and 7 in vitro shows that the organic-directing ligands and their complexes inhibit VEGFR2 phosphorylation. Besides, L2, L4, 3, and 7 inhibit the phosphorylation of extracellular signal-regulated kinase 1/2 (ERK1/2) and proto-oncogene tyrosine-protein kinase (Src), capable of acting downstream of VEGFR2 as well as independently. Compounds L2, L4, 3, and 7 have a lesser effect on ERK1/2 and more prominently affect Src phosphorylation. We extended the study for L2 and 3 in the Tg(fli1:gfp) zebrafish model and found that L2 is more effective in vivo compared to 3 in inhibiting angiogenesis.
Synthesis and Evaluation of Pyrazole Derivatives as Potent Antinemic Agents
Dhillon, N. K.,Jain, N.,Kaur, G.,Utreja, D.
, p. 113 - 118 (2020/03/25)
Pyrazole derivatives were synthesized by bromination of pyrazole, followed by N-alkylation of 4-bromopyrazole. The synthesized derivatives were characterized by microanalytical data and IR and 1H and 13C NMR spectra and were evaluated for their nematicidal activity against the root knot nematode Meloidogyne incognita. The compounds were screened for their egg hatch inhibition and mortality potential, and they showed significant nematicidal activity as compared to the control. 1H-Pyrazol-5(4H)-one was found to be most effective in egg hatch inhibition, and 4-bromopyrazole was found to be most effective in juvenile mortality.
PROCESSES AND INTERMEDIATES FOR MAKING A JAK INHIBITOR
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Paragraph 0120-0121, (2019/08/22)
This invention relates to processes and intermediates for making {1-{1-[3-fluoro-2-(trifluoromethyl)isonicotinoyl]piperidin-4-yl}-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile, useful in the treatment of diseases related to the activity of Janus kinases (JAK) including inflammatory disorders, autoimmune disorders, cancer, and other diseases.
Design and Synthesis of Novel Organic Luminescent Materials Based on Pyrazole Derivative
Duan, Yingxiang,Zhao, Qian,Yang, Yanhua,Zhang, Jinyang,Tao, Xuan,Shen, Yingzhong
, p. 1464 - 1471 (2019/03/26)
Five new materials based on pyrazole derivatives have been synthesized and characterized as organic light-emitting devices. This report presents a novel approach to combine pyrazole with aromatic hydrocarbons via methylene. The formed molecules exhibited twisted structures, which resulted in high glass transition temperatures (Tg), which ranged from 83.0 to 101.1°C. They also had high optical band gaps (Eg); most of their optical band gaps are determined by the absorption edge technique as 3.43 to 3.66?eV, evaluated photophysical properties of these synthesized novel chromophores, the optical properties such as maximum absorption and emission wavelengths (λ; nm), molar extinction coefficients (ε; cm?1·M?1), Stokes' shifts (ΔλST; nm), and quantum yields (φF). These compounds exhibited intense absorption bonds between 230 and 350?nm, and the effect of solvent polarity on emission of these pyrazole derivatives was also studied. In addition, they showed blue fluorescence in different solvents and bathochromic shift with the increase in the solvent polarity.
Photocatalytic Oxidative Bromination of Electron-Rich Arenes and Heteroarenes by Anthraquinone
Petzold, Daniel,K?nig, Burkhard
supporting information, p. 626 - 630 (2017/11/22)
The estimated excited oxidation potential of sodium anthraquinone-2-sulfonate (SAS) increases from 1.8 V to about 2.3 V vs SCE by protonation with Br?nsted acids. This increased photooxidation power of protonated anthraquinone was used for the regio-selective oxidative bromination of electron rich (hetero)arenes and drugs in good yield. The mild reaction conditions are compatible with many functional groups, such as double and triple bonds, ketones, amides and amines, hydroxyl groups, carboxylic acids and carbamates. Mechanistic investigations indicate the photooxidation of the arene followed by nucleophilic bromide addition as the likely pathway. (Figure presented.).
ALKYL-AMIDE-SUBSTITUTED PYRIDYL COMPOUNDS USEFUL AS MODULATORS OF IL-12, IL-23 AND/OR IFNα RESPONSES
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Page/Page column 81, (2017/09/02)
Compounds having the following formula I: or a stereoisomer or a pharmaceutically-acceptable salt thereof, wherein R1, R2, R3, R4, and R5 are as defined herein, are useful in the modulation of IL-12, IL-23 and/or IFNα by acting on Tyk-2 to cause signal transduction inhibition.
A mild halogenation of pyrazoles using sodium halide salts and Oxone
Olsen, Kathryn L.,Jensen, Matthew R.,MacKay, James A.
supporting information, p. 4111 - 4114 (2017/09/29)
A mild, inexpensive, and operationally simple pyrazole halogenation method utilizing Oxone and sodium halide salts is reported. This work documents 17 examples of alkyl, aryl, allyl, and benzyl substituted 4-chloro and 4-bromopyrazoles, obtained in up to 93% yield. Reactions are performed in water under ambient conditions and generation of organic byproducts is avoided.
