7188-22-9

Usage

Heterocyclic compound

Consisting of a phthalazine ring system 1-Phenylphthalazine contains a ring structure made up of carbon and nitrogen atoms, which is characteristic of heterocyclic compounds.

Phenyl group attachment

Attached to one of the nitrogen atoms A phenyl group, which is a benzene ring with a single carbon-carbon double bond, is connected to the phthalazine ring system via one of the nitrogen atoms.

Use in organic synthesis

Building block 1-Phenylphthalazine serves as a starting material or intermediate in the synthesis of more complex organic compounds.

Pharmaceutical research

Potential applications in drug discovery The compound may be used as a precursor or template for the development of new pharmaceuticals.

New materials development

Possible role in creating new materials 1-Phenylphthalazine may be utilized in the design and synthesis of novel materials with unique properties.

Biological activities

Being studied for potential effects Researchers are investigating the possible biological activities of 1-Phenylphthalazine, including its role as an antioxidant and enzyme inhibition capabilities.

Antioxidant properties

Potential role as an antioxidant 1-Phenylphthalazine may have the ability to neutralize harmful free radicals and protect cells from oxidative damage.

Enzyme inhibition

Ability to inhibit specific enzymes The compound may be able to interfere with the activity of certain enzymes, which could have therapeutic applications.

Further research needed

Limited understanding of properties and uses While 1-Phenylphthalazine has shown promise in various areas, more research is required to fully comprehend its properties and potential applications.

Upstream product

• 10132-01-1 1-chloro-4-phenyl-phthalazine 
• 65997-87-7 (E,Z)-Benzaldehyde azine 
• 119-61-9 benzophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 253-52-1 PHTHALAZINE 
• 100-58-3 phenylmagnesium bromide 
• 5784-45-2 1-chlorophthalazine 
• 98-80-6 phenylboronic acid 
• 774506-23-9 1-phenyl-1,2,3,4-tetrahydro-phthalazine 
• 24469-50-9 t-butyl 3-benzylidenecarbazate 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 100-52-7 benzaldehyde 
• 204520-35-4 (4-Methoxy-phenyl)-(4-phenyl-phthalazin-1-yl)-methanone 
• 10034-85-2 hydrogen iodide 

Downstream Products

• 26641-30-5 4-isopropylidene-1,1-dimethyl-7-phenyl-1,11b-dihydro-[1,3]oxazino[4,3-a]phthalazin-2-one 
• 13225-63-3 2,3-Dihydro-4-phenyl-1H-benzindene 
• 774506-23-9 1-phenyl-1,2,3,4-tetrahydro-phthalazine 
• 101277-90-1 1-(2′-hydroxyphenyl)naphthalene 

Relevant academic research and scientific papers

Regiocontrolled and Stereoselective Syntheses of Tetrahydrophthalazine Derivatives using Radical Cyclizations

Tetrahydrophthalazine derivatives have found important applications in pharmaceutical research, but existing synthetic methods are unable to access them regio- and stereoselectively. Here, a new approach is presented that addresses these challenges by utilizing a 6-endo-trig radical cyclization in the key step. The desired tetrahydrophthalazines can be accessed in high yields (55–98 %) and high diastereoselectivities for the trans-product (>95:5) starting either from readily accessible hydrazones, or from the corresponding aldehydes and substituted Boc-hydrazides in a one-pot process. The synthetic versatility of the tetrahydrophthalazine core was demonstrated by its straightforward conversion to dihydro-phthalazines, phthalazines, or pyrazolo dione derivatives. Furthermore, the N?N bond was reduced to afford a new route to 1,4-diamines.

C-H functionalization directed by transformable nitrogen heterocycles: Synthesis of ortho-oxygenated arylnaphthalenes from arylphthalazines

Two protocols for oxygenation of aromatic C-H bonds ortho-positioned to the phthalazine ring were developed. The transannulation of the phthalazine ring to a naphthalene moiety by an Inverse Electron Demand Diels-Alder (IEDDA) reaction led to the synthesis of naphtho[2,1-c]chromenes, 1-(ortho-hydroxyaryl) naphthalenes and 6,7-dihydrobenzo[b]naphtho[1,2-d]oxepine. This new strategy based on the utilization of transformable nitrogen heterocycles in C-H functionalization chemistry can be potentially applicable to the synthesis of a broad range of biaryl compounds.

Cycloadditions of siloxy alkynes with 1,2-diazines: From reaction discovery to identification of an antiglycolytic chemotype

Cycloaddition uncovered: The title reaction produces novel polycyclic compounds with high efficiency and excellent diastereoselectivity under mild reaction conditions. A small-molecule library, synthesized using this reaction, yielded a novel chemotype which inhibited glycolytic ATP production by blocking glucose uptake in CHO-K1 cells. DMF=N,N-dimethylformamide, Tf= trifluoromethanesulfonyl, TIPS=triisopropylsilyl. Copyright

One-pot synthesis of phthalazines and pyridazino-aromatics: A novel strategy for substituted naphthalenes

A new one-pot strategy for the synthesis of phthalazines and pyridazino-aromatics starting from aromatic aldehydes has been developed. A variety of substituents ranging from electron withdrawing to donating is tolerated furnishing the desired 1,2-diazine in good to excellent yields. The products have been applied to the bidentate Lewis acid catalyzed inverse electron-demand Diels-Alder (IEDDA) reaction opening a novel two-step entry into substituted naphthalenes, such as Naproxen.

Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase

This invention relates to bis mono- and/or bicyclic aryl and/or heteroaryl compounds exhibiting protein tyrosine kinase inhibition activity. More specifically, it relates to the method of inhibiting abnormal cell proliferation in a patient suffering from a disorder characterized by such proliferation comprising the administration thereto of an EGF and/or PDGF receptor inhibiting effective amount of said bis mono- and/or bicyclic aryl and/or heteroaryl compound and to the preparation of said compounds and their use in pharmaceutical compositions used in this method.

Carbon-carbon bond cleavage of α-hydroxybenzylheteroarenes catalyzed by cyanide ion: Retro-benzoin condensation affords ketones and heteroarenes and benzyl migration affords benzylheteroarenes and arenecarbaldehydes

4-(α-Benzylα-hydroxybenzyl)quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4, 9, 12, 16-19) having an α-hydroxybenzyl group at the α-position of the nitrogen underwent retro-benzoin type condensation to afford kelones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13, 14, 15) having an α-benzyl-α-hydroxybelzyl group resulted in benzyl migration, giving benzylpyrazolopyrimidines (8) and arenecarbaldehydes (3). Tetrabutylammonium cyanide (11, Bu4NCN) was a more effective cyanide ion donor than KCN (10). The retro-benzoin condensation was applied to the synthesis of 2-substituted quinazolines (38) from 2-chloro-4- aroylquinazolines (34), using the aroyl group as a protecting and electron- withdrawing group.

PHTHALAZINE DERIVATIVES FROM AROMATIC ALDAZINES

A Lewis acid mediated synthesis of phthalazine derivatives II and III from aromatic aldazines I is reported.