80369-11-5

Usage

Physical state

Yellow solid

Uses

Synthesis of pharmaceuticals and other organic compounds

Chemical structure

Isoindoline-1,3-dione derivative with a butyl group and a carbonyl group

Applications

Building block in organic synthesis, production of various drugs and industrial chemicals

Biological activity

Potential activity, subject of ongoing research in medicinal chemistry

Upstream product

• 1074-82-4 potassium phtalimide 
• 616-27-3 1-chlorobutan-2-one 
• 136918-14-4 phthalimide 
• 816-40-0 1-Bromo-2-butanone 
• 88332-07-4 (R,S)-N-(2-hydroxy-1-butyl)-phthalimide 
• 78-93-3 butanone 
• 85-44-9 phthalic anhydride 

Downstream Products

• 25716-33-0 7-ethylpteridine 
• 108661-54-7 1-amino-2-butanone hydrochloride 

Relevant academic research and scientific papers

Synthesis of diverse acyclic precursors to pyrroles for studies of prebiotic routes to tetrapyrrole macrocycles

A chemical model for the origin of tetrapyrrole macrocycles under prebiotic conditions entails the condensation of acyclic dicarbonyl compounds and α-aminoketones to form pyrroles that are equipped for subsequent self-condensation. Development and exploration of the scope of the chemical model (including combinatorial reactions, studies of the effects of structurally defective substrates, and reactions in aqueous or organic media) have relied on the availability of diverse starting materials prepared by traditional chemical synthesis methods. Here the synthesis of all acyclic dicarbonyl compounds and α-aminoketones used in the prior prebiotic model studies is described. There are five sets of acyclic dicarbonyl compounds including (i) β-ketoesters bearing diverse 4-substituents, (ii) levulinic acid derivatives bearing selected 5-substituents (i.e., analogues of δ-aminolevulinic acid, ALA), (iii) meso-substituted β-ketoesters, (iv) meso-substituted β-diketones that contain one 4-substituent, and (v) hybrid molecules that contain both the β-ketoacyl unit and the levulinic acid skeleton (or homologue thereof). A variety of α-aminoketones (homologues of ALA) also have been prepared. Altogether, the synthesis of 53 compounds is described, encompassing 28 new compounds as well as 25 known compounds that have been more fully characterized or prepared via alternative routes. The ability to convert selected acyclic compounds directly via pyrroles to porphyrinogens in a single-flask process may also prove useful in mainstream syntheses of diverse tetrapyrroles regardless of possible prebiotic relevance.

Concise synthesis of 1H-pyrazin-2-ones and 2-aminopyrazines

Convenient syntheses of 1H-pyrazin-2-ones and 2-aminopyrazines are described. By coupling Boc-protected amino acids with α-amino ketones or with amino alcohols and subsequent oxidation, 1H-pyrazin-2-ones were obtained. Transformation into the corresponding pyrazine triflates and substitution with primary or secondary amines led to 2-aminopyrazines. Since these syntheses take advantage of the use of readily available starting materials (e.g., amino acids, aminoalcohols and amines) a variety of the entitled structures can be obtained in few, high yielding steps.

The chemistry of pseudomonic acid. 15. Synthesis and antibacterial activity of a series of 5-alkyl, 5-alkenyl, and 5-heterosubstituted oxazoles

The synthesis of a range of 5-alkyl, 5-alkenyl, and 5-heterosubstituted 2- (1-normon-2-yl) oxazoles is described. The antibacterial activity was determined as the minimum inhibitory concentration against a range of Gram- positive and Gram-negative organisms using a standard Agar dilution procedure. Compounds possessing an acid functionality directly on, or close to, the ring were found to be of greatly decreased potency, while increasing lipophilicity with greater chain length led to increased potency of these derivatives.

Hypolipidemic activity of phthalimide derivatives. IV: Further chemical modification and investigation of the hypolipidemic activity of N-substituted imides

A further investigation of N-substituted derivatives of phthalimide for hypolipidemic activity has revealed that the chain length, as well as the type of substitution on the N-alkyl chain of phthalimide is critical for biological activity. In these studies the hypolipidemic activity was not improved by extending the chain length beyond five carbon atoms in the alkyl and alkanoic acid series. Imido nitrogen substitutents, other than alkanoic acids, methyl ketones, and alkyl groups, caused a reduction in hypolipidemic activity, e.g., hydroxy, amino, hydroxymethyl, or carbethoxy. Reduction of the keto group in the side chain to an alcohol, as well as forming derivatives of the keto group, did not improve the hypolipidemic activity with the exception of 1-N-phthalimidobutan-3-one semicarbazone. This compound demonstrated improved hypocholesterolemic activity over phthalimide and 1-N-phthalimidobutan-3-one. Substitution of the 3-position of the aromatic moiety of phthalimide with an amino or nitro group, as well as substituting a pyridine or cyclohexyl ring for the phenyl ring, led to the loss of hypolipidemic activity.

Phthalimido alkanone, ethylene ketals

Phthalimides of the Formula SPC1 Wherein X is NH2, N(CH3)2, Cl or Br and R0 and R1 are hydrogen, methyl or ethyl are disclosed as intermediates in the preparation of benzodiazepines.