1994-40-7

Basic information

• Product Name: 1-(1-(4-fluorophenyl)ethylidene)-2-phenylhydrazine
• Synonyms: 1-(1-(4-fluorophenyl)ethylidene)-2-phenylhydrazine
• CAS NO: 1994-40-7
• Molecular Weight: 228.269
• Mol File: 1994-40-7.mol
• Article Data: 69

Chemical Properties

• CAS DataBase Reference: 1-(1-(4-fluorophenyl)ethylidene)-2-phenylhydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-(4-fluorophenyl)ethylidene)-2-phenylhydrazine(1994-40-7)
• EPA Substance Registry System: 1-(1-(4-fluorophenyl)ethylidene)-2-phenylhydrazine(1994-40-7)

Safety Data

• Hazardous Substances Data: 1994-40-7(Hazardous Substances Data)

Upstream product

• 403-42-9 1-(4-fluorophenyl)ethanone 
• 59-88-1 phenylhydrazine hydrochloride 
• 100-63-0 phenylhydrazine 

Downstream Products

• 370098-34-3 3-(4-fluorophenyl)-1-phenyl-1H-pyrazole-4-carboxylic acid 
• 373627-27-1 3-(4-fluoro-phenyl)-1-phenyl-1H-pyrazole-4-carbonyl chloride 
• 1431855-43-4 2-(2,4-dimethoxyphenylamino)-5-[3-(4-fluoro-phenyl)-1-phenyl-1H-pyrazol-4-ylmethylene]thiazol-4-one 
• 36640-40-1 3-(4-fluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 70093-12-8 2-(p-fluorophenyl)-1H-indole-3-carboxaldehyde 
• 1351939-92-8 2-amino-4-(2-(4-fluorophenyl)-1H-indol-3-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 1351939-91-7 2-amino-4-(2-(4-fluorophenyl)-1H-indol-3-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 1346173-83-8 (Z)-5-((3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidine-2,4-dione 
• 1394896-63-9 2-(3-(2-chlorophenyl)-5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one 
• 1394896-62-8 2-(5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one 
• 1394897-05-2 5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 
• 1394897-04-1 5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-3-(2-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 
• 1394897-03-0 5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-3-p-tolyl-4,5-dihydro-1H-pyrazole-1-carbothioamide 
• 1394897-02-9 5-(3-(4-Fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-3-o-tolyl-4,5-dihydro-1H-pyrazole-1-carbothioamide 

Relevant articles and documents

Design, synthesis and biological evaluation of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives as potential BRAFV600E inhibitors

A series of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives (6a-10d) were designed, synthesized and evaluated as BRAFV600E inhibitors. Biological evaluation assays indicated that compound 10a showed the most potent inhibitory activity against A375, WM266.4 and BRAFV600Ein vitro with IC50 values of 1.36 μM, 0.94 μM and 0.11 μM respectively compared with the positive compound vemurafenib. Furthermore, compound 10a showed highly selective BRAFV600E inhibitory activity in vitro. A docking simulation displayed that compound 10a could tightly bind the crystal structure of BRAFV600E at the active site. 3D-QSAR would provide a guideline to design and optimize more potent and positive BRAFV600E inhibitors based on the (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives skeleton.

Synthesis, molecular modeling and biological evaluation of cinnamic acid derivatives with pyrazole moieties as novel anticancer agents

A series of pyrazole derivatives (1e-30e) has been designed and synthesized, and their biological activities were evaluated for EGFR and HER-2 inhibition and tumor cell antiproliferation. Among the compounds synthesized, compound 30e exhibited excellent enzyme inhibitory activity (IC50 = 0.21 ± 0.05 μM for EGFR and IC50 = 1.08 ± 0.15 μM for HER-2). Compound 30e also showed the most potent antiproliferative activity, which inhibited the growth of MCF-7 and B16-F10 cell lines with IC50 values of 0.30 ± 0.04 and 0.44 ± 0.05 μM, respectively. The molecular docking study was performed to analyze the probable binding models and the 3D-QSAR models were built for the rational design of EGFR/HER-2 inhibitors. Based on the results obtained, compound 30e with potent EGFR and HER-2 inhibitory activity may be a potential anticancer agent. the Partner Organisations 2014.

Discovery of N-(benzyloxy)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives as potential antiproliferative agents by inhibiting MEK

Mitogen activated protein kinase (MAPK) signal transduction pathway has been proved to play an important role in tumorigenesis and cancer development. MEK inhibitor has been demonstrated significant clinical benefit for blocking MAPK pathway activation and possibly could block reactivation of the MAPK pathway at the time of BRAF inhibitor resistance. Twenty N-(benzyloxy)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives have been designed and synthesized as MEK inhibitors, and their biological activities were evaluated. Among these compounds, compound 7b showed the most potent inhibitory activity with IC50of 91?nM for MEK1 and GI50value of 0.26?μM for A549 cells. The SAR analysis and docking simulation were performed to provide crucial pharmacophore clues that could be used in further structure optimization.

(E)-1,3-diphenyl-1H-pyrazole derivatives containing O-benzyl oxime moiety as potential immunosuppressive agents: Design, synthesis, molecular docking and biological evaluation

A series of novel (E)-1,3-diphenyl-1H-pyrazole derivatives containing O-benzyl oxime moiety were firstly synthesized and their immunosuppressive activities were evaluated. Among all the compounds, 4n exhibited the most potent inhibitory activity (IC50 Combining double low line 1.18 μM for lymph node cells and IC50 Combining double low line 0.28 μM for PI3Kγ3), which was comparable to that of positive control. Moreover, selected compounds were tested for their inhibitory activities against IL-6 released in ConA-simulated mouse lymph node cells, 4n exhibited the most potent inhibitory ability. Furthermore, in order to study the preliminary mechanism of the compounds with potent inhibitory activity, the RT-PCR experiment was performed to assay the effect of selected compounds on mRNA expression of IL-6. Among them, compound 4n strongly inhibited the expression of IL-6 mRNA.

Pyrazolo-benzothiazole hybrids: Synthesis, anticancer properties and evaluation of antiangiogenic activity using in vitro VEGFR-2 kinase and in vivo transgenic zebrafish model

A series of new pyrazolo-benzothiazole hybrids (7–26) were synthesised and screened for their cytotoxic activity towards several cancer cell lines [colon (HT-29), prostate (PC-3), lung (A549), glioblastoma (U87MG)] and normal human embryonic kidney cell line (Hek-293T). Compounds 8, 9, 13, 14, 18, 19, 23, and 24 displayed significant activity, with compound 14 being particularly potent towards all the tested cancer cell lines with IC50 values in the range 3.17–6.77 μM, even better than reference drug axitinib (4.88–21.7 μM). Compound 14 also showed the strongest growth inhibition in 3D multicellular spheroids of PC-3 and U87MG cells. The mechanism of cellular toxicity in PC-3 cells was found to be cell cycle arrest and apoptosis induction through depolarisation of mitochondrial membrane potential, increased ROS production and subsequent DNA damage. Further, compound 14 displayed significant in vitro (VEGFR-2 inhibition) and in vivo [transgenic zebrafish Tg(flila:EGFP) model] antiangiogenic properties. Overall, these results provide strong evidence that compound 14 could be considered for a lead candidate in anticancer and antiangiogenic drug discovery.

Design and synthesis of pyrazole–pyrazoline hybrids as cancer-associated selective COX-2 inhibitors

In continuation of our previous work on cancer and inflammation, 15 novel pyrazole–pyrazoline hybrids (WSPP1–15) were synthesized and fully characterized. The formation of the pyrazoline ring was confirmed by the appearance of three doublets of doublets in 1H nuclear magnetic resonance spectra exhibiting an AMX pattern for three protons (HA, HM, and HX) of the pyrazoline ring. All the synthesized compounds were screened for their in vitro anticancer activity against five cell lines, that is, MCF-7, A549, SiHa, COLO205, and HepG2 cells, using the MTT growth inhibition assay. 5-Fluorouracil was taken as the positive control in the study. It was observed that, among them, WSPP11 was found to be active against A549, SiHa, COLO205, and HepG2 cells, with IC50 values of 4.94, 4.54, 4.86, and 2.09 μM. All the derivatives were also evaluated for their cytotoxicity against HaCaT cells. WSPP11 was also found to be nontoxic against normal cells (cell line HaCaT), with an IC50 value of more than 50 μM. The derivatives were also evaluated for their in vitro anti-inflammatory activity by the protein (egg albumin) denaturation assay and the red blood cell membrane stabilizing assay, using diclofenac sodium and celecoxib as standard. Compounds that showed significant anticancer and anti-inflammatory activities were further studied for COX-2 inhibition. The manifestation of a higher COX-2 selectivity index of WSPP11 as compared with other derivatives and an in vitro anticancer activity against four cell lines further established that compounds that were more selective toward COX-2 also exhibited a better spectrum of activity against various cancer cell lines.

B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions

An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.