67592-40-9

Usage

InChI:InChI=1/C14H9NO2/c16-13-10-3-1-2-4-11(10)14(17)12(13)9-5-7-15-8-6-9/h1-8,16H

Upstream product

• 108-89-4 picoline 
• 85-44-9 phthalic anhydride 
• 606-23-5 1H-indene-1,3(2H)-dione 
• 15854-87-2 4-iodopyridine 
• 872-85-5 pyridine-4-carbaldehyde 
• 87-41-2 2-benzofuran-1(3H)-one 

Downstream Products

• 1242606-57-0 C₂₆H₂₅FN₆O 
• 1242606-77-4 C₂₆H₂₄Cl₂N₆O 
• 1242606-79-6 C₂₈H₃₀N₆O 
• 1242606-81-0 C₂₆H₂₅ClN₆O 
• 1242606-83-2 C₂₈H₃₀N₆O 
• 1242606-85-4 C₂₇H₂₇FN₆O 
• 1313222-83-1 C₂₈H₂₄F₆N₆O 
• 1313222-85-3 C₂₆H₂₅FN₆O 
• 1313222-86-4 C₂₇H₂₅F₃N₆O₂ 
• 1313222-87-5 C₂₆H₂₅ClN₆O 
• 1313222-88-6 C₂₇H₂₅F₃N₆O 
• 1313222-84-2 C₂₇H₂₈N₆O 
• 212141-54-3 vatalanib 

Relevant academic research and scientific papers

Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones

A straightforward and feasible palladium-catalyzed direct α-arylation of indane-1,3-dione to 2-substituted aryl/heteroaryl indene-1,3-diones has been disclosed for the first time. Optimization of reaction conditions identified tBu-XPhos as a preferred ligand for the bis(acetonitrile)dichloropalladium(II) catalyst. A broad spectrum of aryl iodides and aryl triflates containing electron-donating, electron-withdrawing, and sterically hindered substituents gave an excellent yield for the quick access α-arylated 1,3-diones library.

Synthesis and cytotoxic evaluation of some new phthalazinylpiperazine derivatives

A new series of 1,4-disubstituted phthalazinylpiperazine derivatives 7a-f, 12a-f and 20a-f were designed and synthesized in order to develop potent and selective antitumor agents. The target compounds were screened for their cytotoxic activities against A549, HT-29 and MDA-MB-231 cancer cell lines in vitro. Among them, compounds 7a-f exhibited excellent selectivity for MDA-MB-231 with IC50 values ranging from 0.013 μM to 0.079 μM. The most promising compound, 7e (IC50 = 2.19 μM, 2.19 μM, 0.013 μM), was 9.3, 10, and 4.9 × 103 times more active than vatalanib (IC50 = 20.27 μM, 21.96 μM, 63.90 μM), respectively. A new series of 1,4-disubstituted phthalazinylpiperazine derivatives 7a-f, 12a-f and 20a-f were designed and synthesized, and their cytotoxic activities against A549, HT-29 and MDA-MB-231 cancer cell lines in vitro were compared to that of vatalanib.

Synthesis and antitumor activities of novel 1,4-disubstituted phthalazine derivatives

In an attempt to develop potent and selective antitumor agents,a series of novel 1,4-disubstituted phthalazine derivatives was designed and synthesized. All the prepared compounds were screened for their cytotoxic activities against A549,HT-29 and MDA-MB-231 cell lines in vitro. Among them,seven compounds (7a7e,7j and 7i) displayed excellent selectivity for MDA-MB-231 cells with IC50 values in the nM range,a desirable range for pharmacological testing. The most promising compound,7a (IC50 = 3.79 μ M,2.32 μ M,0.84 nM),was 5.6-,10.8-and 6.9 × 104-times more active than PTK-787 (IC50 = 21.16 μ M,22.11 μ M,57.72 μ M),respectively.

Synthesis and antitumor activities of novel 1,4-substituted phthalazine derivatives

A series of 1,4-substituted phthalazine derivatives were designed and synthesized. All the prepared compounds were screened for their cytotoxic activities against A549, HT-29 and MDA-MB-231 cell lines in vitro. Among them, compounds 7a-7h showed excellent selectivity for MDA-MB-231 cell line with IC50 values from 1nmol/L to 0.92μmol/L. A preliminary SAR study of these derivatives was performed.

DIARYLAMINE-CONTAINING COMPOUNDS AND COMPOSITIONS, AND THEIR USE AS MODULATORS OF STEROID HORMONE NUCLEAR RECEPTORS

Described herein are compounds that include a diarylamine structural feature. Also described herein are methods for making such compounds, methods for using such compounds to modulate the activity of steroid hormone nuclear receptors, and pharmaceutical compositions and medicaments comprising such compounds. Also described herein are methods of using such compounds, pharmaceutical compositions and medicaments to treat and/or prevent diseases or conditions associated with the activity of steroid hormone nuclear receptors.

New anilinophthalazines as potent and orally well absorbed inhibitors of the VEGF receptor tyrosine kinases useful as antagonists of tumor-driven angiogenesis

The sprouting of new blood vessels, or angiogenesis, is necessary for any solid tumor to grow large enough to cause life-threatening disease. Vascular endothelial growth factor (VEGF) is one of the key promoters of tumor induced angiogenesis. VEGF receptors, the tyrosine kinases Flt-1 and KDR, are expressed on vascular endothelial cells and initiate angiogenesis upon activation by VEGF. 1-Anilino-(4-pyridylmethyl)-phthalazines, such as CGP 79787D (or PTK787/ZK222584), reversibly inhibit Flt-1 and KDR with IC50 values 50 = 34 nM). Modification of the 1-anilino moiety afforded derivatives with higher selectivity for the VEGF receptor tyrosine kinases Flt-1 and KDR compared to the related receptor tyrosine kinases PDGF-R and c-Kit. Since these 1-anilino-(4-pyridylmethyl)phthalazines are orally well absorbed, these compounds qualify for further profiling and as candidates for clinical evaluation.