153885-60-0

Upstream product

• 457-77-2 ethyl 4-fluorophenylcarbamate 
• 459-25-6 N-(4-fluorophenyl)formamide 
• 1195-45-5 para-fluorophenyl isocyanate 
• 659-30-3 1-(4-fluorophenyl)urea 
• 371-40-4 4-fluoroaniline 
• 65141-04-0 phenyl N-(4-fluorophenyl)carbamate 

Downstream Products

• 80240-40-0 4-(4-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1180533-01-0 C₂₈H₃₀ClFN₆O₃S₂ 
• 1198272-49-9 1-(2-ethyl-4-oxo-4H-quinazolin-3-yl)-3-(4-fluoro-phenyl)-urea 
• 1198272-38-6 1-(4-fluoro-phenyl)-3-(4-oxo-2-phenyl-4H-quinazolin-3-yl)-urea 
• 1268368-49-5 C₁₅H₁₄FN₃O₂ 
• 659-30-3 1-(4-fluorophenyl)urea 
• 1309469-91-7 4-[(10S)-dihydroartemisinin-10-oxycarbonyl]benzaldehyde N₄-(4-fluorophenyl)semicarbazone 
• 1309469-88-2 4-[(10S)-dihydroartemisinin-10-oxy]benzaldehyde N₄-(4-fluorophenyl)semicarbazone 
• 1356965-19-9 2-[(1E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(4-fluorophenyl)hydrazinecarboxamide 
• 1356965-27-9 (5RS)-5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-N-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide 
• 1357066-52-4 4-[(5-[4-fluorophenylamino]-1,3,4-oxadiazol-2-yl)methylamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 
• 1596368-63-6 (E)-1-{[(7-dimethylamino)-2-oxo-2H-chromen-3-yl]methylidene}-4-(4-fluorophenyl)semicarbazone 

Relevant academic research and scientific papers

Design and synthesis of new 2,5-disubstituted-1,3,4-oxadiazole analogues as anticancer agents

In continuance of our search for new anticancer agents, we report herein the design, synthesis, and anticancer evaluation of oxadiazole analogues. Two series (4a-h and 4i-q) of new oxadiazole analogues were designed based on heterocyclic (1,3,4-oxadiazole

Synthesis, In-vitro evaluation and molecular docking studies of oxoindolin phenylhydrazine carboxamides as potent and selective inhibitors of ectonucleoside triphosphate diphosphohydrolase (NTPDase)

Members of the ectonucleoside triphosphate diphosphohydrolases (NTPDases) constitute the major family of enzymes responsible for the maintenance of extracellular levels of nucleotides and nucleosides by catalyzing the hydrolysis of nucleoside triphosphate

Insight on a new indolinone derivative as an orally bioavailable lead compound against renal cell carcinoma

A series of novel 3-indolinone-thiazolidinones and oxazolidinones 4a-k was synthesized via molecular hybridization approach and sequentially evaluated to explore its cytotoxic activity. The cytotoxicity screening pointed toward the N-cyclohexyl thiazolidinone derivative 4f that revealed promising renal cytotoxicity against CAKI-1 and UO-31 renal cancer cell lines with IC50 values 4.74 and 3.99 μM, respectively, which were comparable to those of sunitinib along with good safety threshold against normal renal cells. Further emphasis on compound 4f renal cytotoxicity was achieved via different enzyme assays and CAKI-1 and UO-31 cell cycle analysis. The results were supported by in silico studies to explore its physicochemical, pharmacokinetic and drug-likeness properties. Finally, compound 4f was subjected to an in vivo pharmacokinetic study through two different routes of administration showing excellent oral bioavailability. This research represents compound 4f as a promising candidate against renal cell carcinoma.

Design, synthesis, and biological evaluation of sorafenib derivatives containing indole (ketone) semicarbazide analogs as antitumor agents

A series of new sorafenib derivatives was designed and synthesized. The antiproliferative activity of the synthesized compounds against human lung cancer cell (A549), human pancreatic cancer cell (PC-3), human leukemia cell (K562), and human hepatoma cell (SMMC-7721) was evaluated by MTT assay. The results revealed that several compounds displayed more significant antitumor activities than commercial anticancer agent sorafenib against SMMC-7721. In addition, compounds 7a, 7g, 7l, 7m, and 7p represented obvious growth inhibition with IC50 values of 1-9 μM against four cancer cell lines, demonstrating more predominant activities against cancer cells as compared to sorafenib. Furthermore, some structure-activity relationships have also been established. Compounds containing indole and benzene ring substituted by halogen showed better activity than sorafenib. Wound healing assay suggested that cells would be targeted on their migratory capacity by 7g, potentially affecting the migration activity of these tumors. The effects of A549 and PC-3 cell apoptosis induced by compound 7g were significantly increased compared with sorafenib. Importantly, the result of western blot assay showed that 7g inhibited cell growth by suppressing the activity of EGFR, especially the expression of p-EGFR (Tyr1068).

Design and synthesis of novel N-(4-(Pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides as potential anticonvulsant agents

A new series of N-(4-(pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides (PSSD1-8) were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for their possible anticonvulsant activity. All the derivatives were synthesized by the given scheme and reaction process was monitored by thin layer chromatography. The structure of synthesized derivatives was confirmed by FT-IR, 1H NMR, mass spectroscopy and elemental analysis. The anticonvulsant activity was established after intraperitoneal administration in MES and scMET seizure models. The most active compound of the series was 1-(4-(pyridin-2-yloxy)-benzylidene)-4-p-tolylsemicarbazide (PSSD5). A molecular docking study was carried out in order to assess the interaction and binding modes with target receptor/enzyme. Titled compounds were found to strongly bind to human gamma-aminobutyric acid receptor (GABAAR-β3). A computational study was also carried to predict the pharmacokinetic properties of the synthesized compounds.

Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides

The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.

Design, synthesis and anticancer activity of dihydropyrimidinone-semicarbazone hybrids as potential human DNA ligase 1 inhibitors

A series of new dihydropyrimidinone-semicarbazone hybrids were successfully synthesised by integrating regioselective multicomponent reaction with the pharmacophore hybridization approach. All the synthesised compounds were evaluated for their hLig1 inhibition potency and most of them were found to be good to moderately active. Out of the tested derivatives, compound 6f showed selective anti-proliferative activity against HepG2 cells in a dose-dependent manner with an IC50 value of 10.07 ± 1.2. It also reduced cell survival at ≤20 μM concentration. Further, analysis of treated HepG2 cell lysates by western blot assay showed increased γ-H2AX levels and upregulation of p53, leading to apoptosis. In silico docking results explain the binding modes of compound 6f to the DNA-binding domain of hLig1 enzyme thereby preventing its nick sealing activity. In addition, the favourable pharmacokinetic properties suggest that this new class of hLig1 inhibitors could be promising leads for further drug development.

Synthesis of N-aryl and N-arylcarbamoylamino derivatives of 1,3-diazinane-5-carboxamide and their activity against glioblastoma LN-229 cell line

Six structural motifs based on the initial (lead) structure of merbarone were designed, prepared, and tested against the glioblastoma LN-229 cell line. Three different structural moieties were modified in the search for optimal glioblastoma activity: the 1,3-diazinane moiety, the aryl moiety, and the heteroatom linker. Calculated molecular descriptors such as lipophilicity (C log P), acidic strength (calculated pKa), and polar surface area (PSA) were used to design a diverse structural library of these compounds. From six different structural motifs and 136 compounds, a handful of examples with moderate (100 μg/ml), good (10 μg/ml) and excellent (1 μg/ml) glioblastoma activity were elucidated.

Isatin N-phenylsemicarbazone: Effect of substituents and concentration on anion sensing selectivity and sensitivity

The effect of substituent and concentration on anion sensing selectivity and sensitivity of nine new easily synthesized isatin N-phenylsemicarbazone E-isomer sensors IIIa-XIa was investigated. The substantial difference between the association constants for IIIa-XIa interaction with strongly and weakly basic anions allows detection of F- or CH3COO- anions even at high weakly basic anion excess. Substitution in position 5- of the isatin ring and para-substitution on the phenyl ring in the phenylsemicarbazide chain influence sensor:anion complex stoichiometry and thus also sensor sensitivity. Detection limits of 3-4 × 10-7 mol dm-3 for F- and CH3COO- anions by sensors IVa and Va bearing electron-withdrawing substituents are among the lowest published detection limits for these anions in organic solvents. The high selectivity and sensitivity of sensor VIa allows confident F- detection at tolerated fluoride drinking-water level. The solution dilution leads to a dramatic change in sensor selectivity. Consequently, one E-isomer can be used to sense both strongly and weakly basic anions. On the other side, higher sensor solution concentrations increase the F- and CH3COO- anion detection range, similar to the additional Z-isomer utilization. This journal is

3-(7-Dimethylamino)coumarin N-phenylsemicarbazones in solution and polymer matrices: Tuning their fluorescence via para-phenyl substitution

The photo-physical properties of five new para-phenyl substituted derivatives of 3-(7-dimethylamino)coumarin N-phenylsemicarbazone with various electron-withdrawing substituents R (RF, Br, CF3, CN or NO 2) in the para-position on the phenyl ring were investigated in solvents and in polymer matrices. Tuning their fluorescent properties via para-substitution is discussed in terms of Twisted Intra-molecular Charge-Transfer (TICT) state formation, specific solute-solvent interactions (hydrogen bonding), fluorescent H-aggregates formation, and the solvent polarity and polymer matrix effects.