72287-77-5

Usage

Uses

Used in Pharmaceutical Industry:
DMAA is used as a precursor in the synthesis of various pharmaceutical compounds for its ability to facilitate the formation of amides, esters, and ketones, which are essential in the development of new drugs.
Used in Chemical Synthesis:
In the chemical industry, DMAA is utilized as a reagent in the production of dyes, insecticides, and herbicides, contributing to the creation of a wide range of products that serve different purposes.
Used in Research and Development:
DMAA has been studied for its potential use as an analgesic and antipyretic drug, indicating its application in the research and development of new medications aimed at pain relief and fever reduction.
Used in Safety and Handling:
It is crucial to handle DMAA with care due to its potential harmful effects if ingested, inhaled, or absorbed through the skin, emphasizing its application in safety protocols within laboratories and manufacturing facilities.

InChI:InChI=1/C4H10N2O.ClH/c1-6(2)4(7)3-5;/h3,5H2,1-2H3;1H

Upstream product

• 72287-76-4 N-[2-(dimethylamino)-2-oxoethyl]carbamic acid 1,1-dimethylethyl ester 
• 3392-07-2 tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}carbamate 
• 124-40-3 dimethyl amine 

Downstream Products

• 1251933-11-5 2-(5-chloro-3-(2-(dimethylamino)-2-oxoethylamino)-6-methyl-2-oxopyrazin-1(2H)-yl)-2-phenylacetic acid methyl ester 
• 1092977-61-1 2-[2-(3-butoxyphenyl)ethylamino]-N,N-dimethylacetamide 
• 1357917-76-0 2-benzylideneamino-N,N-dimethylacetamide 

Relevant academic research and scientific papers

Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination

We describe herein a crystallographic and NMR study of the secondary structural attributes of a β-turn-containing tetra-peptide, Boc-Dmaa-d-Pro-Acpc-Leu-NMe2, which was recently reported as a highly effective catalyst in the atroposelective bromination of 3-arylquinazolin-4(3H)-ones. Inquiries pertaining to the functional consequences of residue substitutions led to the discovery of a more selective catalyst, Boc-Dmaa-d-Pro-Acpc-Leu-OMe, the structure of which was also explored. This new lead catalyst was found to exhibit a type I′ β-turn secondary structure both in the solid state and in solution, a structure that was shown to be an accessible conformation of the previously reported catalyst, as well.

Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination

We report the development of a tertiary amine-containing β-turn peptide that catalyzes the atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional theory calculations and are discussed in light of the high enantioselectivities observed. Mechanistic studies also suggest that the initial bromination event is stereodetermining, and the major monobromide intermediate is an atropisomerically stable, mono-ortho-substituted isomer. The observation of stereoisomerically stable monobromides stimulated the conversion of the tribromide products to other atropisomerically defined products of interest. For example, (1) a dehalogenation Suzuki-Miyaura cross-coupling sequence delivers ortho-arylated derivatives, and (2) a regioselective Buchwald-Hartwig amination procedure installs para-amine functionality. Stereochemical information was retained during these subsequent transformations.

Peptide-catalyzed conversion of racemic oxazol-5(4 H)-ones into enantiomerically enriched α-amino acid derivatives

We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

Conformational analysis of β-turn structure in tetrapeptides containing proline or proline analogs

In order to evaluate the influence of cyclic secondary amino acids on the stability of β-turn structure, we have prepared Ac-Gly-L-Xxx-L-Leu-Gly-N(CH3)2 (Xxx = Aze, 4-membered ring: 1, Xxx = Pro, 5-membered ring: 2, Xxx = Pip, 6-membered ring: 3). The NOE cross peaks that support β-turn structure were observed in 1-3. The NOE cross peak between both terminals of the synthetic peptides, however, was observed only in the NOESY spectra of 2. This result indicates that 5-membered ring side chain in proline plays a very important role in the formation of β-hairpin structure.

Structural and thermodynamic characterization of temperature-dependent changes in the folding pattern of a synthetic triamide

Variable-temperature 1H NMR and IR studies of triamide 1 and related compounds indicate that 1 undergoes dramatic temperature-dependent conformational changes in relatively nonpolar solvents (methylene chloride and chloroform). The folding pattern favored at low temperatures in these chlorocarbons (1c) contains a single C=O?H-N hydrogen bond in a nine-membered ring, while a folding pattern containing only a six-membered-ring C=O?N-H interaction (1a) is favored at higher temperatures. Dimethyl sulfoxide, a very strong hydrogen-bond-accepting solvent, disrupts all internal hydrogen bonding in 1. Acetonitrile appears to disrupt the six-membered-ring hydrogen bond selectively and to promote nine-membered-ring interaction at room temperature, relative to chlorocarbon solvents. By treating the behavior of 1 as a two-state system, in which folding pattern 1c is considered to be the "native state" and all other folding patterns comprise the "denatured state", we have been able to carry out van't Hoff analyses of the temperature-dependent conformational changes. In methylene chloride, the native state is enthalpically preferred by 1.9-2.5 kcal/mol but entropically disfavored by 7.4-9.1 eu. Similar values are obtained in chloroform. This thermodynamic characterization demonstrates that, even in a relatively nonpolar environment, the relative enthalpic stabilities of alternative folding patterns cannot be predicted simply by maximizing the pairing of hydrogen-bond donors and acceptors.

N-N-DISUBSTITUTED-OMEGA-(2-AMINO-3-(CARBONYLMETHYL)-3,4-DIHYDROQUINAZOLINYL)OXY-ALKYLAMIDES AND RELATED COMPOUNDS

Compounds are disclosed according to the formula or an optical isomer thereof. The compounds of formula I are cyclic AMP phosphodiesterase inhibitors useful as antithrombotic and inotropic agents and the like in mammals

N-N-disubstituted-ω-[2-amino-3-(carbonylmethyl)-3, 4-dihydroquinazolinyl]oxyalkylamides and related compounds

Pharmaceutical compositions comprising, or compositions consisting essentially of, compounds according to the formula STR1 or an optical isomer thereof are disclosed, wherein the substituents A, Z and R1 are defined herein. The invention is also directed to certain compounds of the above class. The compounds of Formula I are cyclic AMP phosphodiesterase inhibitors useful as antithrombotic and inotropic agents and the like in mammals.