18393-54-9

Basic information

• Product Name: 2-methyl-2,3-dihydro-1,4-phthalazinedione
• Synonyms: 2-methyl-2,3-dihydro-1,4-phthalazinedione
• CAS NO: 18393-54-9
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17202
• Mol File: 18393-54-9.mol

Chemical Properties

• Boiling Point: 364.6°Cat760mmHg
• Flash Point: 174.3°C
• Appearance: /
• Density: 1.292g/cm³
• Vapor Pressure: 5.91E-06mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 2-methyl-2,3-dihydro-1,4-phthalazinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-2,3-dihydro-1,4-phthalazinedione(18393-54-9)
• EPA Substance Registry System: 2-methyl-2,3-dihydro-1,4-phthalazinedione(18393-54-9)

Safety Data

• Hazardous Substances Data: 18393-54-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H8N2O2/c1-11-9(13)7-5-3-2-4-6(7)8(12)10-11/h2-5H,1H3,(H,10,12)

Upstream product

• 615-42-9 1,2-Diiodobenzene 
• 201230-82-2 carbon monoxide 
• 60-34-4 methylhydrazine 
• 208183-97-5 2-[3-(4-Chloro-phenyl)-prop-2-ynyloxy]-isoindole-1,3-dione 
• 108-24-7 acetic anhydride 
• 85-44-9 phthalic anhydride 

Downstream Products

• 111297-94-0 N-acetyl-sulfanilic acid-(3-methyl-4-oxo-3,4-dihydro-phthalazin-1-ylamide) 
• 109446-98-2 sulfanilic acid-(3-methyl-4-oxo-3,4-dihydro-phthalazin-1-ylamide) 
• 40227-54-1 4-chloro-2-methylphthalazin-1-(2H)-one 

Relevant articles and documents

Synthesis, biological evaluation and structure-activity relationships of new phthalazinedione derivatives with vasorelaxant activity

Five series of 1,4-phthalazinedione derivatives were synthesized in good yields. Vasorelaxant activity of these new derivatives was measured on either intact or endothelium-denuded isolated rat thoracic aortic rings pre-contracted with phenylephrine. Most of studied compounds, substituted in both nitrogen atoms, attained practically the total relaxation of the organ at low micromolar concentrations. The presence of functional endothelium significantly reduced the EC50 values for most of studied compounds. Some structure-activity relationships were established and compounds 2d and 5d can be considered as new leads for further modifications.

Design, synthesis and antitumor activity of phthalazine-1,4-dione-based menaquinone analogs

New chemotherapeutics are needed to treat hepatocellular carcinoma (HCC), and menaquinones, homologs of vitamin K consisting of a 1,4-naphthoquinone core and a (poly)isoprene chain, are potential candidates. In this study, we designed and synthesized a series of phthalazine-1,4-dione-based menaquinone analogs. Among them, compounds bearing the intact isoprene chain exhibited selective antiproliferative activity towards HCC cell line JHH7, as compared with normal hepatocytes. The geranyl derivative 10 showed submicromolar potency, and might be a promising lead compound for anticancer agents.

Simple and condensed β-lactams. Part 22. An unprecedented ring transformation accompanying dephthaloylation of a 3-phthalimidoazetidin-2-one

Dephthaloylation of 3-phthalimidoazetidin-2-one 1a with methylhydrazine affords the ring transformation product 2b, rather than the expected 3-aminoazetidin-2-one 1b. Independently prepared azetidinone 1b, when treated with sodium hydroxide or methylhydra

PHTHALAZINE DERIVATIVES OF FORMULA (I) AS PCAF AND GCN5 INHIBITORS FOR USE IN THE TREATMENT OF CANCER

The present invention relates to methods for treating PCAF and GCN5 mediated disorders using a compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein ring A, R1, R3, R4, R5, and each Re have any of the values defined in the specification. Also included are novel compounds of Formula (I) and salts thereof, as well as pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof.

Synthesis of tetrahydrophthalazine and phthalamide (phthalimide) derivatives via palladium-catalysed carbonylation of iodoarenes

1,2,3,4-Tetrahydrophthalazin-1-one and 1,2,3,4-tetrahydrophthalazin-1,4- dione derivatives were synthesised in high (up to 85%) and low yields using 2-iodobenzyl bromide and 1,2-diiodobenzene as bifunctional substrates, respectively. Iodoarenes, carbon monoxide and various hydrazine derivatives as N-nucleophiles were used in a three-component palladium-catalysed cascade hydrazinocarbonylation. A similar palladium-catalysed reaction, the aminocarbonylation of 1,2-diiodobenzene, resulted mainly in the formation of two types of major products depending on the amine N-nucleophiles: the use of primary amines yielded N-substituted phthalimides in double carbonylation, while secondary amines react with one of the iodoarene functionalities affording the corresponding 2-iodobenzamides. Due to double carbon monoxide insertion at one or both iodoarene functionalities, ketocarboxamide-carboxamide or bis-ketocarboxamide derivatives could be isolated by the modification of the reaction conditions. Some mechanistic details of the ring-closure reactions and the conditions leading to side-products are also discussed.

Solid-supported synthesis of artificial phospholipids

A concise solid-supported synthesis of artificial phospholipids was developed. Functionalized phospholipids were prepared by introduction of a head group onto a solid-supported phospholipid framework in good overall yield and purity. Georg Thieme Verlag S

The preparation of 2-isoxazolines from O-propargylic hydroxylamines via a tandem rearrangement-cyclisation reaction

A method for the conversion of O-propargylic hydroxylamines into 2-isoxazolines in 60-84% yield is described. For 3-alkylpropargyl or 3-arylpropargyl hydroxylamines this was achieved by heating a methanolic solution of the hydrochloride salt in the presen

Benzopyrans

A compound of the formula: STR1 or a pharmaceutically acceptable salt thereof, wherein X is O, S or NH; R and R1 are each independently selected from H and C1 -C4 alkyl or taken together represent C2 -C6 alkylene; R2 is H or C1 -C4 alkyl; R3 is a 6-membered heterocyclic ring containing 2N hetero-atoms, said ring being linked to X by a ring carbon atom, optionally benzo-fused and optionally substituted, including in the benzo-fused portion, by C1 -C6 alkyl, hydroxy, --OR5, halo, --S(O)m R5, oxo, amino, --NHR5, --N(R5)2, cyano, --CO2 R5, --CONH2, --CONHR5 or --CON(R5)2, with the proviso that R3 is not an N--(C1 -C6 alkyl)pyridonyl group; R4 is phenyl substituted by a hydroxy group and optionally further substituted by 1 or 2 substitutents each independently selected from hydroxy, C1 -C6 alkyl, --OR5, halo, cyano and nitro; R5 is C1 -C6 alkyl; R6 is --OR5, --NHR5, --N(R5)2, --SR5 or --NHR9 ; R7 is cyano; R8 is --OR5, --NHR5, --N(R5)2, or --NHR9 ; R9 is phenyl optionally substituted by C1 -C6 alkyl, hydroxy, --OR5, halo, cyano or nitro; and m is 0, 1 or 2.

ATP-sensitive potassium channel openers: Synthesis and antihypertensive activity of 4-bicycloxybenzopyrans

Synthesis and hypotensive activity of trans-3,4-dihydro-3-hydroxy-4-[(5-oxo-3,4-diazabicyclo[4.1.0]hept-2-en-2 -yl)oxy]-2H-1-benzopyrans and their congeners are described. Compounds (-)-9eB and (-)-20B were highly potent ATP-sensitive potassium channel openers.