5439-98-5

Usage

InChI:InChI=1/C14H10N2O2/c17-13-11-8-4-5-9-12(11)14(18)16(15-13)10-6-2-1-3-7-10/h1-9H,(H,15,17)

Upstream product

• 85-44-9 phthalic anhydride 
• 64-17-5 ethanol 
• 100-63-0 phenylhydrazine 
• 532-96-7 N-benzoyl-N'-phenylhydrazine 
• 622-84-4 2-formyl-1-phenylhydrazine 
• 4870-16-0 N-anilinophthalimide 
• 59-88-1 phenylhydrazine hydrochloride 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 140902-41-6 3,3'-Diphenyl-2,2'(3H,3'H)-biphthalazin-1,1',4,4'-tetron 
• 136918-14-4 phthalimide 
• 90-15-3 α-naphthol 
• 73006-31-2 phthalic acid mono-(N'-acetyl-N-phenyl-hydrazide) 
• 29110-76-7 2-[(2-phenylhydrazino)carbonyl]benzoic acid 

Downstream Products

• 103512-22-7 4-octadec-9c-enyloxy-2-phenyl-2H-phthalazin-1-one 
• 109813-75-4 4-benzyloxy-2-phenyl-2H-phthalazin-1-one 
• 18691-66-2 4-benzoyloxy-2-phenyl-2H-phthalazin-1-one 
• 108668-02-6 2-phenyl-4-propoxy-2H-phthalazin-1-one 
• 101444-56-8 4-allyloxy-2-phenyl-2H-phthalazin-1-one 
• 194863-94-0 4-methoxy-2-phenyl-2H-phthalazin-1-one 
• 93716-69-9 2-(4-nitrophenyl)-1,4-phthalazinediones 
• 296803-14-0 2-phenyl-2,3-dihydro-1,4-phthalazinedithione 
• 859300-04-2 2,2'-diphenyl-2H,2'H-4,4'-sulfanediyl-bis-phthalazine-1-thione 
• 732-26-3 2,4,6-tri-tert-butylphenoxol 
• 140902-42-7 2,3-Dihydro-2-phenyl-3-(1,3,5-tri-tert-butyl-4-oxocyclohexa-2,5-dien-1-yl)phthalazin-1,4-dion 
• 92-52-4 biphenyl 
• 61446-38-6 C₁₄H₉N₂O₂ 
• 140902-41-6 3,3'-Diphenyl-2,2'(3H,3'H)-biphthalazin-1,1',4,4'-tetron 

Relevant academic research and scientific papers

Ru(II)-Catalyzed C-H Hydroxyalkylation and Mitsunobu Cyclization of N-Aryl Phthalazinones

Ruthenium(II)-catalyzed C(sp2)-H functionalization of N-Aryl phthalazinones with a range of aldehydes and activated ketone is described. Initial formation of hydroxyalkylated phthalazinones and subsequent Mitsunobu cyclization provided facile access to biologically relevant indazolophthalazinones. The utility of this method is highlighted by synthetic transformations into a series of potentially bioactive scaffolds.

Phthalazinone-Assisted C-H Amidation Using Dioxazolones under Rh(III) Catalysis

The preparation of phthalazinone derivatives is pivotal for their utilization as pharmaceutical agents and other entities. Herein, we report the phthalazinone-assisted carbon-nitrogen bond forming reaction using dioxazolones as robust amidation sources under Rh(III) catalysis. The broad functional group tolerance and complete site-selectivity are observed. Notably, a series of transformations of synthesized compounds into biologically relevant N-heterocycles demonstrates the applicability of the developed methodology.

Selective Synthesis in Microdroplets of 2-Phenyl-2,3-dihydrophthalazine-1,4-dione from Phenyl Hydrazine with Phthalic Anhydride or Phthalic Acid

Pyridazine derivatives are privileged structures because of their potential biological and optical properties. Traditional synthetic methods usually require acid or base as a catalyst under reflux conditions with reaction times ranging from hours to a few days or require microwave assistance to induce the reaction. Herein, this work presents the accelerated synthesis of a pyridazine derivative, 2-phenyl-2,3-dihydrophthalazine-1,4-dione (PDHP), in electrosprayed microdroplets containing an equimolar mixture of phenyl hydrazine and phthalic anhydride or phthalic acid. This reaction occurred on the submillisecond timescale with good yield (over 90 % with the choice of solvent) without using an external catalyst at room temperature. In sharp contrast to the bulk reaction of obtaining a mixture of two products, the reaction in confined microdroplets yields only the important six-membered heterocyclic product PDHP. Results indicated that surface reactions in microdroplets with low pH values cause selectivity, acceleration, and high yields.

Palladium-Catalyzed Direct ortho-C–H Bond Sulfonylation and Halogenation of Phthalazine-1,4-diones

The regio- and chemo-selective Pd-catalyzed C–H activation methods have been successfully reported for directed C–H sulfonation and halogenation of pyridazinedione with arylsulfonyl chlorides and N-halosuccinimide, respectively. These protocols are compatible with a range of various functional groups and exhibit excellent regio-selectivity under mild reaction conditions by use of inexpensive and readily accessible reagents.

A ruthenium-catalyzed alkenylation-annulation approach for the synthesis of indazole derivatives via C-H bond activation

Ruthenium catalyzed oxidative alkenylation of N-aryl pyridazinediones and N-aryl phthalazinediones with acrylates and subsequent intramolecular cyclization of the resulting product in water as a green solvent were accomplished. Diverse derivatives of pyridazino[1,2-a]indazoles and indazolo[1,2-b]phthalazines were readily prepared in moderate to high yields by this methodology from easily accessible starting materials via cascade directed C-H bond activation/annulation reactions.

Ru(II)-Catalyzed C-H Activation and Annulation Reaction via Carbon-Carbon Triple Bond Cleavage

An unprecedented Ru(II)-catalyzed C-H activation and annulation reaction, which proceeds via C-C triple bond cleavage, is reported. This reaction of 2-phenyldihydrophthalazinediones with alkynes, which works most efficiently in the presence of bidented ligand 1,3-bis(diphenylphosphino)propane, affords good yields of substituted quinazolines.

INHIBITORS OF IRES-MEDIATED PROTEIN SYNTHESIS

This disclosure relates to inhibitors of IRES-mediated protein synthesis, compositions comprising therapeutically effective amounts of these compounds, and methods of using those compounds and compositions in treating hyperproliferative disorders, e.g., cancers. This disclosure also relates to compositions comprising inhibitors of IRES-mediated protein synthesis and mTOR inhibitors, and to methods of treating cancer by conjoint administration of inhibitors of IRES-mediated protein synthesis and mTOR inhibitors.

Synthesis of cinnolines via Rh(III)-catalysed dehydrogenative C-H/N-H functionalization: Aggregation induced emission and cell imaging

Rhodium catalysed dehydrogenative C-H/N-H functionalization was developed to construct phthalazino[2,3-a]-/indazolo[1,2-a]cinnolines by reacting N-phenyl phthalazine/indazole with alkynes. The synthesized compounds exhibit prominent fluorescence properties in solid and aggregation states. Their application in cell imaging was investigated using various cancer cell lines.

Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones

Ruthenium-catalyzed simple, cascade and one-pot synthesis of cinnoline-fused diones has been carried out by the C-H activation of phthalazinones/pyridazinones accomplished by the unusual deoxygenation of propargyl alcohols. The bond selectivity is accredited to the traceless directing nature of the hydroxyl group of propargyl alcohol. A sequential C-H activation, insertion and deoxy-oxidative annulation has been proposed based on the preliminary mechanistic study.

The identification of the 2-phenylphthalazin-1(2 H)-one scaffold as a new decorable core skeleton for the design of potent and selective human A 3 adenosine receptor antagonists

Following a molecular simplification approach, we have identified the 2-phenylphthalazin-1(2H)-one (PHTZ) ring system as a new decorable core skeleton for the design of novel hA3 adenosine receptor (AR) antagonists. Interest for this new series was driven by the structural similarity between the PHTZ skeleton and both the 2-aryl-1,2,4-triazolo[4,3-a]quinoxalin-1-one (TQX) and the 4-carboxamido-quinazoline (QZ) scaffolds extensively investigated in our previously reported studies. Our attention was focused at position 4 of the phthalazine nucleus where different amido and ureido moieties were introduced (compounds 2-20). Some of the new PHTZ compounds showed high hA3 AR affinity and selectivity, the 2,5-dimethoxyphenylphthalazin-1(2H)-one 18 being the most potent and selective hA3 AR antagonist among this series (Ki = 0.776 nM; hA1/hA3 and hA 2A/hA3 > 12000). Molecular docking studies on the PHTZ derivatives revealed for these compounds a binding mode similar to that of the previously reported TQX and QZ series, as was expected from the simplification approach.