57353-93-2

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Methoxyphenyl)-1-(2H)-phthalazinone is used as a building block for the preparation of bioactive molecules, specifically [4-(4-methoxyphenyl)-1(2H)-oxo-phthalazin-2-yl]acetic acid ethyl ester, which exhibits potent antibacterial activity. This application is significant in the development of new antibiotics to combat bacterial infections.
Additionally, due to its role as a building block for bioactive molecules, 4-(4-Methoxyphenyl)-1-(2H)-phthalazinone may also be utilized in the synthesis of other pharmaceutical compounds with various therapeutic applications, such as anti-inflammatory, antiviral, or anticancer agents. Its versatility in molecular construction makes it a valuable asset in the pharmaceutical industry for the development of novel drugs.

InChI:InChI=1/C15H12N2O2/c1-19-11-8-6-10(7-9-11)14-12-4-2-3-5-13(12)15(18)17-16-14/h2-9H,1H3,(H,17,18)

Upstream product

• 1151-15-1 2-(4-methoxybenzoyl)benzoic acid 
• 34403-64-0 N-(p-chlorobenzylideneamino)phthalimide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 32387-12-5 N-naphthalen-1-ylmethyleneamino-phthalimide 
• 32387-13-6 N-naphthalen-2-ylmethyleneamino-phthalimide 
• 100-66-3 methoxybenzene 
• 18110-71-9 4'-methoxybiphenyl-2-carboxylic acid 
• 85-44-9 phthalic anhydride 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1875-48-5 N-aminophthalamide 

Downstream Products

• 128615-83-8 1-chloro-4-(4-methoxyphenyl)phthalazine 
• 127828-84-6 [4-(4-methoxyphenyl)-1(2H)-oxophthalazin-2-yl]acetic acid ethyl ester 
• 134389-95-0 4-(4-methoxyphenyl)-2-methyl-1(2H)-phthalazinone 
• 1354719-98-4 4-(4-methoxyphenyl)-2-[3-[4-[3-(acetylamino)phenyl]piperidin-1-yl]propyl]phthalazin-1(2H)-one 
• 23752-28-5 4-(4-methoxyphenyl)-2-(3-chloropropyl)phthalazin-1(2H)-one 
• 120116-67-8 4-(4'-methoxyphenyl)-1-hydrazinophthalazine 

Relevant academic research and scientific papers

Preparation method and epoxidation application of phthalazinone bisphenol monomer

The invention belongs to the technical field of new materials, and discloses a preparation method and epoxidation application of a phthalazinone bisphenol monomer. The method comprises the following steps: (1) preparing MHPZ by a Friedel-Crafts reaction; (2) synthesizing an MMPZ monomer by using the MHPZ, 4-bromoanisole (BPM), 1,10-phenanthroline (PNTM) and CuI by a "one-pot two-step method"; and(3) reducing the MMPZ by Lewis acid to obtain the target monomer HHPZ. The synthesis method has the advantages of mild reaction condition, simple and convenient product post-treatment and high productpurity. Through detection by liquid chromatography-mass spectrometry, the purity of the target monomer is 99% and the yield is 90% or above. Based on the above synthetic exploration, two ends of thesynthesized active bisphenol monomer were further functionalized. Active hydroxyl groups at two ends of HHPZ are epoxidized with epichlorohydrin, and then novel intrinsic flame retardant epoxy resin with a low melting point and high temperature resistance is achieved, wherein the flame retardant grade can reach the V-0 grade.

TOLL-LIKE RECEPTOR 8 (TLR8)-SPECIFIC ANTAGONISTS AND METHODS OF MAKING AND USES THEREOF

Toll-like receptor 8 (TLR8)-specific inhibitors and methods of using the same in individuals having an autoimmune disease or an inflammatory disorder.

Synthesis of 1,2-dihydro-1-oxophthalazin-4-yl trifluoromethanesulfonate and its application in the synthesis of 4-(aryl/heteroaryl/alkynyl)phthalazin-1(2H)-one

The regioselective synthesis of 1,2-dihydro-1-oxophthalazin-4-yl trifluoromethanesulfonate (3a) has been reported. The reaction of Tf2O (2a) with phthalhydrazide (1a) provides a rapid access to 3a with an excellent yield and a high level of reg

NITROGENOUS FUSED HETEROAROMATIC RING DERIVATIVE

The invention provides a compound or its pharmaceutically-acceptable salt of formula (I): wherein A1 is a hydrogen, etc.; j and k are 0 or 1; is a double bond, etc.; is a double bond, etc.; one of W1 and W2 is E-O-W, etc., and the other is a hydrogen atom, etc.; E is a divalent group derived from a benzene ring, etc., by removing two hydrogen atoms therefrom; W is a group of formula (II-1): which has a histamine-H3 receptor antagonistic effect or a histamine-H3 receptor inverse-agonistic effect and is useful for prevention or remedy of metabolic system diseases, circulatory system diseases or nervous system diseases.

New antithrombotic 1-Phthalazinamines with Serotonin Antagonistic Properties

We report nineteen 4-aryl- and 4-arylalkyl-1-phthalazinamines (5-8) which we prepared and tested for antithrombotic properties. All compounds were assayed for their antiplatelet activity in the "Born test" with collagen as inducer of the aggregation. N-[4-(1H-1,2,4-triazol-1-yl)butyl]-4-phenyl-1-phthalazin-amine (7c) was the most potent compound, having an IC50 of 8 μM. When 5-HT (Serotonin) was used to start aggregation the N-(furan-2-yl-methyl)-4-phenyl-1-pthtalazinamine (8a) had an IC50 of 2 μM. In vivo potencies were highly significant. N-[5-(1H-1,2,4-triazol-1-yl)pentyl]-4-phenyl-1-phthalazinamine (7d) inhibited thrombus formation by 12% (P 2A receptor, which is most likely the mechanism of the inhibition of aggregation by this compound.

Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-imidazolyl)alkyl]- 1(2H)-phthalazinones

A number of 4-substituted 2-[ω-(1-imidazolyl)alkyl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane A2 synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.

N-AMINOPHTHALIMIDE AS PRECURSOR FOR 4-ARYLPHTHALAZ-1-ONES

Reaction of N-aminophthalimide of N-arylideneaminophthalimides with hydrocarbons under Friedel-Crafts conditions offer a new parthway for the preparation of 4-arylphthalaz-1-ones (3).

SYNTHESIS AND BEHAVIOUR OF N-NAPHTHYLMETHYLENEAMINOPHTHALIMIDES TOWARD NUCLEOPHILIC REAGENTS

The reactions of N-naphthylmethyleneaminophthalimides (1a, b) with Grignard reagents took place either by normal addition to one of the carbonyl groups to give 2a, d, or by 1,2-addition and cleavage to give 4-arylphthalaz-1-ones (4a-d).The reactions of 1a, b with amines gave 5, 6 and 7, respectively.

Cleavage Reactions of N-Arylmethyleneaminophthalimides with Nucleophilic Reagents

N(p-Chlorobenzylideneamino)phthalimide (1a) reacts with phenylmagnesium bromide and benzylmagnesium chloride to give 3-hydroxy-3-phenyl-2-(α-phenyl-p-chlorobenzylamino)-1-isoindolinone (3) and o-phenacetylbenzoic acid α-phenyl-p-chlorobenzylhydrazide (4), respectively while with p-tolyl- and p-methoxyphenyl-magnesium bromides the cleavage products (5a and 5b) are obtained.Phthalimides (1a-c) when reacted with benzylamine undergo cleavage to give N,N-dibenzylphthalamide (6).N-p-Methoxybenzylideneaminophthalimide (1b) fails to react with phenylhydrazine or maleic anhydride.However, N-aminophthalimide (2) reacts with maleic anhydride to give the acid (8).