25233-46-9

Usage

Uses

Used in Recreational Drug Market:
3-OXO-N-M-TOLYL-BUTYRAMIDE is used as a recreational drug for its stimulant and empathogenic effects, providing users with a sense of euphoria, increased energy, and social closeness. However, its use is controversial and restricted in many jurisdictions due to the associated health risks and potential for abuse.
Used in Research Chemicals:
In the scientific community, 3-OXO-N-M-TOLYL-BUTYRAMIDE is utilized as a research chemical to study the effects of psychoactive substances on the human brain and body. This helps researchers understand the mechanisms of action and potential therapeutic applications of similar compounds.

InChI:InChI=1/C11H13NO2/c1-8-4-3-5-10(6-8)12-11(14)7-9(2)13/h3-6H,7H2,1-2H3,(H,12,14)

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 108-44-1 1-amino-3-methylbenzene 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 1694-31-1 tert-butyl acetoacetate 

Downstream Products

• 112697-63-9 2-Methyl-[1,8]naphthyridine-3-carboxylic acid m-tolylamide 
• 138201-44-2 N'-[1-Methyl-2-m-tolylcarbamoyl-eth-(E)-ylidene]-phosphorohydrazidic acid diphenyl ester 
• 674-82-8 4-methyleneoxetan-2-one 
• 108-44-1 1-amino-3-methylbenzene 
• 83999-19-3 C₁₇H₁₅N₄O₈^(1-)*C₆H₁₅N*H⁽¹⁺⁾ 
• 2585-18-4 4,7-dimethyl-1,2-dihydroquinolin-2-one 
• 61643-59-2 2-[1-Ethoxy-meth-(E)-ylidene]-3-oxo-N-m-tolyl-butyramide 
• 53761-46-9 1,4,7-trimethyl-1H-quinolin-2-one 
• 1607002-98-1 3-acetyl-1-(m-tolyl)-1H-chromeno[4,3-b]pyridine-2,5-dione 
• 1452145-08-2 C₂₉H₂₉N₃O₃ 
• 1452145-56-0 C₁₈H₂₀N₂O 

Relevant academic research and scientific papers

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene

Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Br?nsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.

Structure-Activity Relationship Studies of Tetrahydroquinolone Free Fatty Acid Receptor 3 Modulators

Free fatty acid receptor 3 (FFA3, previously GPR41) is activated by short-chain fatty acids, mediates health effects of the gut microbiota, and is a therapeutic target for metabolic and inflammatory diseases. The shortage of well-characterized tool compounds has however impeded progress. Herein, we report structure-activity relationship of an allosteric modulator series and characterization of physicochemical and pharmacokinetic properties of selected compounds, including previous and new tools. Two representatives, 57 (TUG-1907) and 63 (TUG-2015), showed improved solubility and preserved potency. Of these, 57, with EC50 = 145 nM and a solubility of 33 μM, showed high clearance in vivo but is a preferred tool in vitro. In contrast, 63, with EC50 = 162 nM and a solubility of 9 μM, showed lower clearance and seems better suited for in vivo studies. Using 57, we demonstrate for the first time that FFA3 activation leads to calcium mobilization in murine dorsal root ganglia.

Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties

Rapid and facileaccess to novel chromeno[4,3-b]pyridine-2,5-dione derivatives was achieved by a mild base catalysed reaction of 4-chloro-3-formylcoumarin and acetoacetamides in PEG-300 as recyclable solvent. The compounds were evaluated for their antimicrobial activities against 3 Gram-positive and 3 Gram-negative bacteria (Staphylococcus epidermis, Vibrio parahaemolyticus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Klebsiella pneumonia) with Cefotaxime control. They were further subjected to antioxidant studies using DPPH test with ascorbic acid control. While compounds 5d and 5k showed promising broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties. Indian Academy of Sciences.

Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties

Rapid and facile access to novel chromeno[4,3-b]pyridine-2,5-dione derivatives was achieved by a mild base catalysed reaction of 4-chloro-3-formylcoumarin and acetoacetamides in PEG-300 as recyclable solvent. The compounds were evaluated for their antimicrobial activities against 3 Gram-positive and 3 Gram-negative bacteria (Staphylococcus epidermis, Vibrio parahaemolyticus, Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Klebsiella pneumonia) with Cefotaxime control. They were further subjected to antioxidant studies using DPPH test with ascorbic acid control. While compounds 5d and 5k showed promising broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties. [Figure not available: see fulltext.]

Diastereoselective hydrogenation of substituted quinolines to enantiomerically pure decahydroquinolines

The stereoselective hydrogenation of auxiliary-substituted quinolines was used to build up saturated and partially saturated heterocycles. In a first step, the formation and diastereoselective hydrogenation of 2-oxazolidinone- substituted quinolines to 5,6,7,8-tetrahydroquinolines is reported. In this unprecedented process, stereocenters on the carbocyclic quinoline ring were formed with a dr of up to 89:11. Platinum oxide as a catalyst and trifluoroacetic acid as a solvent were found to be optimal for high levels of chemo- and stereoselectivity in this step. In a second hydrogenation step, the completely saturated decahydroquinolines with 4 newly formed stereocenters were obtained with enantioselectivities of up to 99%. Rhodium on carbon as a catalyst and acetic acid as a solvent gave the best results for this hydrogenation and allowed a traceless cleavage of the chiral auxiliary. Thus, this new method allows an efficient stereoselective synthesis of valuable 5,6,7,8-tetrahydro- and decahydroquinoline products.

Synthesis and characterization of N-acylaniline derivatives as potential chemical hybridizing agents (CHAs) for wheat (Triticum aestivum L.)

Induction of male sterility by deployment of chemical hybridizing agents (CHAs) are important in heterosis breeding of self-pollinated crops like wheat, wherein the male and female organs are in the same flower. Taking a lead from the earlier work on rice, a total of 25 N-acylanilines comprising of malonanilates, acetoacetanilides, and acetanilides (including halogenated acetanilides) were synthesized and screened as CHAs on three genotypes of wheat, viz., PBW 343, HD 2046, and HD 2733 at 1500 ppm in the winter of 2001-2002. The N-acylanilines containing variations at the acyl and aromatic domain were synthesized by condensation of substituted anilines with appropriate diesters, acid chlorides, or monoesters. The test compounds with highly electronegative groups such as F/Br at the para position of the aryl ring were identified as the most potent CHAs, causing higher induction of male sterility. A variation of N-substitution at the side chain generally furnished analogues like 4′-fluoroacetoacetanilide (7) and ethyl 4′-fluoromalonanilate (1), which induced 89.12 and 84.66% male sterility, respectively, in PBW 343. Among halogenated acetanilides, the increasing number of chlorine atoms in the side chain led to an increase in the activity of 4′-fluoro (23) and 4′-bromo (24) derivatives of trichoroacetanilides, which induced >87% male sterility. Quantitative structure-activity relationship (QSAR) models indicated the positive contributions of the field effect exemplified by the Swain-Lupton constant (Fp) and negative contributions of the Swain-Lupton resonance constant (R) for the aromatic substitution. The positive influences of parachor (P) for the acyl domain have been underlined. These leads will be significant in explaining the CHA fit in the macromolecular receptor site. The CHAs appeared to act by causing an imbalance in the acid-base equilibrium in pollen mother cells resulting in dissolution of the callose wall by premature callase secretion.

Synthesis and immunosuppressant activity of pyrazole carboxamides

A series of novel pyrazole carboxamides sis disclosed that demonstrate strong immunosuppressant activity in rodent and human mixed leukocyte response (MLR) assays (IC50 1 μM). The synthesis, biological activity, mode of action, and pharmacokinetic properties of this new lead series are discussed.

Synthesis of 7-Methyl-1,2-dihydroquinolin-2-ones as Angiotensin II Receptor Antagonists

A number of biphenyl substituted 1,2-dihydroquinolin-2-ones were synthesized by regiospecific alkylation of the corresponding 1H-derivatives.Again, these precursors were prepared in three steps by acetoacetylation of anilines, regiospecific C-alkylation of the resulting β-ketoanilides and subsequent condensation to the quinolines.One of the target compounds, 2--1,2-dihydroquinolin-3-yl>-N,N-dimethylacetamide (10e), is a potent angiotensin II receptor antagonist.

MECHANISM OF ACETOACETYLATION OF SUBSTITUED ANILINES

Kinetics have been studied of the reaction of diketene with substituted anilines, and the reaction rate has been found to depend on relative permitivity of the system.The rate and equilibrium constants have been calculated by combination of rate and equilibrium relations with the relation by Amis; the constants correlate with the Hammett substituent constants.The reaction does not proceed as a simple bimolecular process.A reaction mechanism has been suggested.