763114-25-6

Basic information

• Product Name: 2-Fluoro-5-[(3-oxo-1(3H)-isobenzofuranylidene)methyl]-benzonitrile
• Synonyms: 2-Fluoro-5-[(3-oxo-1(3H)-isobenzofuranylidene)methyl]-benzonitrile;(Z)-2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)Methyl)benzonitrile;2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)Methyl)benzonitrile;2-Fluoro-5-(3-oxo-3H-isobenzofuran-1-ylidenemethyl)-benzonitrile;Benzonitrile, 2-fluoro-5-[(3-oxo-1(3H)-isobenzofuranylidene)methyl]-;2-fluoro-5-(3-oxo-1,3-dihydroisobenzofuranylidene methyl)benzonitrile;(E)-2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile;2-fluoro-5-[(Z)-(3-oxo-2-benzofuran-1-ylidene)methyl]benzonitrile
• CAS NO: 763114-25-6
• Molecular Formula: C₁₆H₈FNO₂
• Molecular Weight: 265.2386232
• Product Categories: trebectedin
• Mol File: 763114-25-6.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 430.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.38
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Dichloromethane, Tetrahydrofuran
• CAS DataBase Reference: 2-Fluoro-5-[(3-oxo-1(3H)-isobenzofuranylidene)methyl]-benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-5-[(3-oxo-1(3H)-isobenzofuranylidene)methyl]-benzonitrile(763114-25-6)
• EPA Substance Registry System: 2-Fluoro-5-[(3-oxo-1(3H)-isobenzofuranylidene)methyl]-benzonitrile(763114-25-6)

Safety Data

• Hazardous Substances Data: 763114-25-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of poly (ADP-ribose) polymerase (PARP) inhibitors.

Upstream product

• 61260-15-9 dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate 
• 4741-67-7 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid 
• 218301-22-5 2-fluoro-5-formylbenzonitrile 
• 16859-59-9 3-hydroxy-1(3H)-isobenzofuranone 
• 179897-89-3 5-Bromo-2-fluoro-benzonitrile 
• 17858-15-0 trimethylsilyl 2-{(diethoxyphosphoryl)[(diethoxyphosphoryl)oxy]methyl}benzoate 
• 119-67-5 o-carboxybenzaldehyde 
• 77771-02-9 3-bromo-4-fluorobenzaldehyde 

Downstream Products

• 1021298-68-9 2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzonitrile 
• 763114-26-7 2-fluoro-5-[(4’-oxo-3’H-phthalazin-1’-yl)methyl]benzoic acid 
• 763114-04-1 tert-butyl 4-[2’-fluoro-5’-[(4’’-oxo-3’’H-phthalazin-1’’-yl)methyl]benzoyl]piperazine-1-carboxylate 
• 1379676-53-5 1-cyclopropyl-2-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)ethane-1,2-dione 
• 1379676-60-4 1-cyclopropyl-2-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepan-1-yl) ethane-1,2-dione 
• 874116-49-1 tert-butyl 4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepane-1-carboxylate 
• 1379676-62-6 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)-2-phenylethane-1,2-dione 
• 1379676-64-8 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)-3,3-dimethylbutane-1,2-dione 
• 1379676-65-9 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1 -yl)methyl)benzoyl)-1 ,4-diazepan-1-yl)-3,3-dimethylbutane-1,2-dione 
• 1379676-66-0 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepan-1-yl)-2-phenylethane-1,2-dione 
• 1379676-67-1 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepan-1-yl)-2-(furan-2-yl)ethane-1,2-dione 
• 1379676-69-3 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)-2-(furan-2-yl)ethane-1,2-dione 
• 1379676-73-9 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)piperazin-1-yl)propane-1,2-dione 
• 1379676-75-1 1-(4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepan-1-yl)propane-1,2-dione 

Relevant articles and documents

Design, synthesis and activity evaluation of new phthalazinone parp inhibitors

Poly(ADP-ribose)polymerase (PARP) is a significant therapeutic target for the treatment of numerous human diseases. Olaparib has been approved as a PARP inhibitor. In this paper, a series of new compounds were designed and synthesized with Olaparib as the lead compound. In order to evaluate the inhibitory activities against PARP1 of the synthesized compounds, in vitro PARP1 inhibition assay and intracellular PARylation assay were conducted. The results showed that the inhibitory activities of the derivatives were related to the type of substituent and the length of alkyl chain connecting the aromatic ring. 3-(4,5-Dimethyl- 2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT)-based assay also proved that these compounds demonstrating strong inhibition to PARP1 also have high anti-proliferative activities against BRCA2-deficient cell line (Capan-1). Analysis of the entire results suggest that compound 23 with desirable inhibitory efficiency may hold promise for further in vivo exploration of PARP inhibition.

Identification of probe-quality degraders for Poly(ADP-ribose) polymerase-1 (PARP-1)

Poly(ADP-ribose) polymerase-1 (PARP-1), a critical DNA repair enzyme in the base excision repair pathway, has been pursued as an attractive cancer therapeutic target. Intervention with PARP-1 has been proved to be more sensitive to cancer cells carrying BRCA1/2 mutations. Several PARP-1 inhibitors have been available on market for the treatment of breast, ovarian and prostatic cancer. Promisingly, the newly developed proteolysis targeting chimaeras (PROTACs) may provide a more potential strategy based on the degradation of PARP-1. Here we report the design, synthesis, and evaluation of a proteolysis targeting chimaera (PROTAC) based on the combination of PARP-1 inhibitor olaparib and the CRBN (cereblon) ligand lenalidomide. In SW620 cells, our probe-quality degrader compound 2 effectively induced PARP-1 degradation which results in anti-proliferation, cells apoptosis, cell cycle arresting, and cancer cells migratory inhibition. Thus, our findings qualify a new chemical probe for PARP-1 knockdown.

Synthesis, preliminarily biological evaluation and molecular docking study of new Olaparib analogues as multifunctional PARP-1 and cholinesterase inhibitors

A series of new Olaparib derivatives was designed and synthesized, and their inhibitory activities against poly (ADP-ribose) polymerases-1 (PARP-1) enzyme and cancer cell line MDA-MB-436 in vitro were evaluated. The results showed that compound 5l exhibited the most potent inhibitory effects on PARP-1 enzyme (16.10 ± 1.25 nM) and MDA-MB-436 cancer cell (11.62 ± 2.15 μM), which was close to that of Olaparib. As a PARP-1 inhibitor had been reported to be viable to neuroprotection, in order to search for new multitarget-directed ligands (MTDLs) for the treatment of Alzheimer’s disease (AD), the inhibitory activities of the synthesized compounds against the enzymes AChE (from electric eel) and BChE (from equine serum) were also tested. Compound 5l displayed moderate BChE inhibitory activity (9.16 ± 0.91 μM) which was stronger than neostigmine (12.01 ± 0.45 μM) and exhibited selectivity for BChE over AChE to some degree. Molecular docking studies indicated that 5l could bind simultaneously to the catalytic active of PARP-1, but it could not interact well with huBChE. For pursuit of PARP-1 and BChE dual-targeted inhibitors against AD, small and flexible non-polar groups introduced to the compound seemed to be conducive to improving its inhibitory potency on huBChE, while keeping phthalazine-1-one moiety unchanged which was mainly responsible for PARP-1 inhibitory activity. Our research gave a clue to search for new agents based on AChE and PARP-1 dual-inhibited activities to treat Alzheimer’s disease.