Chemoselective and Regiospecific Formylation of 1-Phenyl-1H-pyrazoles Through the Duff Reaction

Monitoring glutathione dynamics in DNA replication (S-phase) using a two-photon reversible ratiometric fluorescent probe

“…At first, the coumarin analogue 1 was obtained through a condensation reaction between 2,4-dihydroxybenzaldehyde and ethyl 4-pyridylacetate. Next, we performed a Duff reaction 29 on coumarin analogue 1 to obtain compound 2 , which was forwarded to the next step without further purification. Finally, a Knoevenagel reaction was carried out between compound 2 and 4-picoline to obtain probe Nu-GSH .…”

Induction of apoptosis in Ehrlich ascites tumour cells via p53 activation by a novel small-molecule MDM2 inhibitor – LQFM030

“…LQFM030 ( 2 ) was produced via the synthetic route shown in Figure , beginning with synthesis of the 1‐(4‐chlorophenyl)‐1 H ‐pyrazole ( 4 ) compound using the classical method described by, with a yield of 92.0%. The 1‐(4‐chlorophenyl)‐1 H ‐pyrazole‐4‐carbaldehyde ( 4 ) compound was produced (with a yield of 77.9%) via chemospecific and region‐specific formulation of 1‐(4‐chlorophenyl)‐1 H ‐pyrazole ( 5 ), which was performed under Duff's conditions . LQFM030 ( 2 ) was obtained under catalytic hydrogenation conditions with a quantitative yield.…”

“…Data collection was performed using φ/ω scans of 0.5° steps and exposure times of 20 s. Data reduction was carried out using SAINT and SADABS, employing the multiscan absorption correction method. The structure solution was accomplished with the direct methods followed by the refinement of structural parameters using F 2 with the full‐matrix least‐squares method; both methods are implemented in the Shelx software package . Non‐hydrogen atoms were refined with anisotropic atomic displacement parameters, and the hydrogen atoms were treated as isotropic and were allowed to depend on their parent atoms with U eq = 1.2 U eq (C aromatic , CH 2 ) and 1.5 U eq (C methyl , O water ).…”

“…The structure solution was accomplished with the direct methods followed by the refinement of structural parameters using F 2 with the full-matrix least-squares method; both methods are implemented in the Shelx software package. [14] Non-hydrogen atoms were refined with anisotropic atomic displacement parameters, and the hydrogen atoms were treated as isotropic and were allowed to depend on their parent atoms with U eq = 1.2 U eq (C aromatic , CH 2 ) and 1.5 U eq (C methyl , O water ). Hydrogen atoms were located in calculated positions, and the hydrogen atoms of the structural water molecule were located in the Fourier difference map and restrained with O-H distance of 0.92 A. Infrared (IR) spectra were obtained with a Nicolet-55a Magna spectrophotometer using potassium bromide plates.…”

“…The 1-(4chlorophenyl)-1H-pyrazole-4-carbaldehyde (4) compound was produced (with a yield of 77.9%) via chemospecific and region-specific formulation of 1-(4-chlorophenyl)-1Hpyrazole (5), which was performed under Duff's conditions. [14] LQFM030 (2) was obtained under catalytic hydrogenation conditions with a quantitative yield. After three steps, LQFM030 (2) was produced with a global yield of 71.6%, which was higher than that of the compound nutlin 1 (1), which was produced with a global yield of 6.4% in eight synthetic.…”