19959-77-4Relevant academic research and scientific papers
New functionalised C,C-pyridylpyrazoles: Synthesis and cation binding properties
Radi, Smaail,Attayibat, Ahmed,Ramdani, Abdelkrim,Bacquet, Maryse
, p. 72 - 74 (2009)
The synthesis of two new C,C-pyridylpyrazole isomers with a functionalised arm is described. The complexation capabilities of these ligands compared to their homologues towards bivalent metals (Hg2+, Cd2+, Pb2+, Cu2+, Zn2+) and alkali metal ions (K +, Na+, Li+) were investigated using a liquid-liquid extraction process. The percentage limits of extraction were determined by atomic absorption measurements.
Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors
Yao, Haiyan,Guo, Quanping,Wang, Mengran,Wang, Rui,Xu, Zhaoqing
, (2021/08/25)
Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.
Discovery of phenylaminopyridine derivatives as novel HIV-1 non-nucleoside reverse transcriptase inhibitors
Kim, Junwon,Park, Changmin,So, Wonyoung,Jo, Mina,Ok, Taedong,Kwon, Jeongjin,Jo, Suyeon,Choi, Jihyun,Kim, Hyoung Cheul,Lee, Doohyun,Kim, Youngmi,Ko, Yoonae,Choi, Inhee,Kong, Sunju,Park, Youngsam,Yoon, Jaewan,Ju, Moon Kyeong,Kim, Junghwan,Han, Sung-Jun,Kim, Tae-Hee,Cechetto, Jonathan,Nam, Jiyoun,Sommer, Peter,Liuzzi, Michel,Lee, Jinhwa,No, Zaesung
supporting information, p. 678 - 682,5 (2020/08/31)
We identified a novel class of aryl-substituted triazine compounds as potent non-nucleoside reverse transcriptase inhibitors (NNRTIs) during a high-throughput screening campaign that evaluated more than 200000 compounds for antihuman immunodeficiency virus (HIV) activity using a cell-based full replication assay. Herein, we disclose the optimization of the antiviral activity in a cell-based assay system leading to the discovery of compound 27, which possessed excellent potency against wild-type HIV-1 (EC50 = 0.2 nM) as well as viruses bearing Y181C and K103N resistance mutations in the reverse transcriptase gene. The X-ray crystal structure of compound 27 complexed with wild-type reverse transcriptase confirmed the mode of action of this novel class of NNRTIs. Introduction of a chloro functional group in the pyrazole moiety dramatically improved hERG and CYP inhibition profiles, yielding highly promising leads for further development.
A simple and efficient synthesis of pyrazoles in water
Wen, Jun,Fu, Yun,Zhang, Ruo-Yi,Zhang, Ji,Chen, Shan-Yong,Yu, Xiao-Qi
supporting information; experimental part, p. 9618 - 9621 (2011/12/14)
A simple, highly efficient, and environmentally friendly method for the synthesis of substituted 1H-pyrazoles by one-pot condensation reaction of α,β-unsaturated carbonyl compounds with tosyl hydrazide in water was developed. The reaction system exhibited tolerance with various functional groups, Aromatic moiety with both electron-rich and electron-deficient substituents could give desired products in good to excellent yields.
Regioselective formation of N-alkyl-3,5-pyrazole derived ligands. A synthetic and computational study
Montoya, Vanessa,Pons, Josefina,Branchadell, Vicen?,Ros, Josep
, p. 12377 - 12385 (2007/10/03)
New N-alkyl-3,5-pyrazole derived ligands were synthesized by reaction between 3,5-pyrazole derived ligands and the appropriate haloalkane in toluene or THF using NaOEt or NaH as base. When the precursor ligand bears a pyridyl substituent the alkylation reaction presents a large regioselectivity. Theoretical calculations have been carried out to rationalize the experimental observations. It has been shown that regioselectivity is governed by the formation of Na+-pyrazolide chelate complexes.
Novel η3-allylpalladium-pyridinylpyrazole complex: Synthesis, reactivity, and catalytic activity for cyclopropanation of ketene silyl acetal with allylic acetates
Satake, Akiharu,Nakata, Tadashi
, p. 10391 - 10396 (2007/10/03)
Novel cationic η3-allylpalladium-pyridinylpyrazole complexes 1a and 1b were synthesized from 3-alkyl-5-(2-pyridinyl)pyrazole and η3-allylpalladium chloride dimer in the presence of AgBF4. Cationic complexes 1a and 1b were converted into neutral complexes 2a and 2b under basic conditions. These complexes were characterized by 1H, 13C, and 15N NMR studies. Neutral complexes 2a and 2b have high catalytic activity for cyclopropanation of ketene silyl acetals with allylic acetates. Comparison of the cationic and neutral complexes and the reaction mechanism of cyclopropanation were discussed.
