21865-87-2

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General Description

2-(2-phenylaziridin-1-yl)-1H-isoindole-1,3(2H)-dione, also known as NSC 663284, is a chemical compound with potential antineoplastic and antitumor effects. It belongs to the class of aziridine-based compounds and has been studied for its ability to inhibit topoisomerase II enzyme activity, which is crucial for DNA replication and cell division. 2-(2-phenylaziridin-1-yl)-1H-isoindole-1,3(2H)-dione has shown promising results in inhibiting the growth of various cancer cell lines, making it a potential candidate for the development of new anti-cancer drugs. Additionally, it has exhibited cytotoxic effects on drug-resistant cancer cells, making it a valuable candidate for overcoming drug resistance in cancer treatment. The structure and properties of 2-(2-phenylaziridin-1-yl)-1H-isoindole-1,3(2H)-dione make it an important target for further research in the field of cancer therapy and drug development.

Upstream product

• 100-42-5 styrene 
• 37802-08-7 1a-acetyl-1-phthalimidoamino-1a,6b-dihydro-1H-benzofuro<2,3-b>azirine 
• 1875-48-5 N-aminophthalamide 
• 134965-34-7 1-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1,1a-dihydro-6-oxa-1-aza-cyclopropa[a]indene-6a-carboxylic acid methyl ester 
• 292638-85-8 acrylic acid methyl ester 

Relevant academic research and scientific papers

Metal-free synthesis of 1,2-amino alcohols by one-pot olefin aziridination and acid ring-opening

A one-pot, two-step reaction comprising olefin aziridination and ring-opening of an aziridine intermediate to synthesize 1,2-amino alcohols has been developed. This reaction is suitable for several types of olefin. This methodology allows an efficient and

Electrocatalytic aziridination of alkenes mediated by n -Bu4NI: A radical pathway

Efficient electrocatalytic aziridination of alkenes has been achieved for the first time. A structurally broad range of aziridines was easily accessed using an undivided cell operated at constant current and mediated by a catalytic quantity of n-Bu4

Sodium-iodoxybenzoate mediated highly chemoselective aziridination of olefins

Herein we utilized, for the first time, sodium 2-iodoxybenzoate as a highly specific oxidant for PhthNH2 to create a highly chemoselective aziridination reagent. This method efficiently effects aziridination of electron-rich, electron-deficient, allylic alcohol and alkenyl bromide C=C bonds in good to excellent yields. Inter and intramolecular chemoselectivity was demonstrated between electron-rich and electron-deficient alkenes by using this efficient and metal free protocol.

Hypoiodite-mediated metal-free catalytic aziridination of alkenes

Look, no metal: A metal-free catalytic procedure for aziridination of alkenes using tetrabutylammonium iodide as the catalyst, m-chloroperoxybenzoic acid (mCPBA) as the terminal oxidant, and N-aminophthalimide as the nitrenium precursor has been developed (see scheme; right: X-ray structure of one of the products). Control experiments suggests that the active oxidant is in situ generated hypoiodous acid (HIO). Copyright

Aryl iodide mediated aziridination of alkenes

(Chemical Equation Presented) Aryl iodide mediated aziridination of a variety of alkenes with N-aminophthalimide under mild conditions (m-CPBA, K 2CO3, CH2Cl2, 25°C) was achieved in moderate to good yields (up to 94%). By recovering the aryl iodide, a recyclable system is developed with product yield over 79% attained for the aziridination of trans-1,2-diphenylethylene.

Superoxide-mediated synthesis of N-aminoaziridines from N-aminoheterocycles and olefins

Oxidation of 3-amino-2-methyl-4(3H)-quinazolone and N-aminophthalimide by superoxide ion generated in situ in the presence of olefinic substrates gives rise to the formation of N-aminoaziridine derivatives. Copyright Taylor & Francis, Inc.

Aziridination of alkenes with N-substituted hydrazines mediated by iodobenzene diacetate

Aziridination of a variety of alkenes with N-substituted hydrazines mediated by iodobenzene diacetate under mild conditions (K2CO 3, CH2Cl2) and ambient temperature were achieved in good to excellent yields (up to 99%), and conversions. The practicality and simplicity of this C-N bond formation protocol was exemplified by its application to the aziridination of cholesteryl acetate in a stereoselective manner.

Aziridination of Alkenes using 3-Acetoxyaminoquinazolin-4-(3H)ones in the Presence of Tertiary Amines: Evidence for an Azaimide (N-Nitrene) Intermediate

Solutions of the triethylammonium imide 8, formed from triethylamine and 3-acetoxyaminoquinazolinone 4, react with alkenes at -30 deg C to give aziridines; the reactivity of the aziridinating intermediate is consistent with its formulation as an azaimide (N-nitrene).

Evidence for Phthalimidonitrene as a Common Intermediate in Several Extrusion Reactions

A common intermediate, presumably phthalimidonitrene 1, is generated in the thermolysis of the aziridinobenzofurans 3 (R = Ac, CO2Me, Bz, COBut and CN) as well as the sulphimide 4, and the azabenzonorbornadiene 5.The transfer of 1 shown in Scheme 1 is zero order in 2-acetylbenzofuran providing further evidence against a concerted bimolecular mechanism 10 for 'nitrene' transfer.

AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES: EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES

Oxidation of 3-aminoquinazolones e.g. (22) with lead tetra-acetate at -20 deg C gives N-acetoxyaminoquinazolones e.g. (23) which are stable in solution at this temperature.These N-acetoxyaminoquinazolones function as inter- and intramolecular aziridinating agents for alkenes and appear to be playing the role previously ascribed to the corresponding N-nitrenes.An analogous N-acetoxyaminophthalimide intermediate (31) is implicated in the lead tetra-acetate oxidation of N-aminophthalimide (4).