15580-32-2

Usage

Uses

Used in Agricultural Industry:
3-ANILINO-3-OXOPROPANOIC ACID is used as a growth regulator and meristem remover for the development of cotton. Its application in this industry is aimed at enhancing the growth and productivity of cotton plants by regulating their growth patterns and removing the meristem, which is the region of undifferentiated cells in the plant responsible for growth and development.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 3073, 1989 DOI: 10.1016/S0040-4039(00)99406-1

InChI:InChI=1/C9H9NO3/c11-8(6-9(12)13)10-7-4-2-1-3-5-7/h1-5H,6H2,(H,10,11)(H,12,13)

Upstream product

• 14438-90-5 N-phenylpropanediamide 
• 53341-66-5 ethyl 3-oxo-3-(phenylamino)propionate 
• 4930-03-4 phenyl N-phenylcarbamate 
• 141-97-9 ethyl acetoacetate 
• 103-84-4 Acetanilid 
• 141-82-2 malonic acid 
• 103-72-0 phenyl isothiocyanate 
• 62-53-3 aniline 
• 105-53-3 diethyl malonate 
• 108-88-3 toluene 
• 16798-45-1 diethyl phenylcarbamoylmalonate 
• 18629-86-2 2-acetyl-N-phenyl-malonamic acid ethyl ester 
• 103-71-9 phenyl isocyanate 
• 2033-24-1 cycl-isopropylidene malonate 

Downstream Products

• 27559-50-8 (E)-3-(4-hydroxyphenyl)-N-phenylacrylamide 
• 340258-57-3 (E)-3-(4-methoxyphenyl)-N-phenylacrylamide 
• 148470-92-2 3-bromo-cinnamic acid anilide 
• 70254-43-2 4-Hydroxy-2-quinolone 
• 40335-02-2 2,3,4-trichloroquinoline 
• 855164-88-4 3ξ-(6-nitro-benzo[1,3]dioxol-5-yl)-acrylic acid anilide 
• 56140-30-8 2-chloro-cinnamic acid anilide 
• 16507-23-6 4,4,4-trichloro-3-hydroxy-butyric acid anilide 
• 27559-49-5 3-(3-hydroxyphenyl)-N-phenyl-2-propenamide 
• 332079-42-2 (E)-3-(3,4-dihydroxyphenyl)-N-phenylacrylamide 

Relevant academic research and scientific papers

Phosphonate as a Stable Zinc-Binding Group for “Pathoblocker” Inhibitors of Clostridial Collagenase H (ColH)

Microbial infections are a significant threat to public health, and resistance is on the rise, so new antibiotics with novel modes of action are urgently needed. The extracellular zinc metalloprotease collagenase H (ColH) from Clostridium histolyticum is a virulence factor that catalyses tissue damage, leading to improved host invasion and colonisation. Besides the major role of ColH in pathogenicity, its extracellular localisation makes it a highly attractive target for the development of new antivirulence agents. Previously, we had found that a highly selective and potent thiol prodrug (with a hydrolytically cleavable thiocarbamate unit) provided efficient ColH inhibition. We now report the synthesis and biological evaluation of a range of zinc-binding group (ZBG) variants of this thiol-derived inhibitor, with the mercapto unit being replaced by other zinc ligands. Among these, an analogue with a phosphonate motif as ZBG showed promising activity against ColH, an improved selectivity profile, and significantly higher stability than the thiol reference compound, thus making it an attractive candidate for future drug development.

One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline

3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.

COMPOUND USED AS AUTOPHAGY REGULATOR, AND PREPARATION METHOD THEREFOR AND USES THEREOF

It is related to compounds used as autophagy modulators and a method for preparing and using the same, specifically providing a compound of general formula (I), or pharmaceutically acceptable salts thereof, which is a type of autophagy modulators, particularly mammalian ATG8 homologues modulators.

Mild, efficient, and solvent-free synthesis of 4-hydroxy-2-quinolinones

Malonic acid monoanilides were obtained in excellent yield from the reaction of anilines with Meldrum's acid under solvent-free conditions. The malonic acid monoanilide intermediates were then treated with methanesulfonic acid anhydride (MSAA) to produce 4-hydroxy-2-quinolinones in excellent yield. It should be noted that both reactions had to be run under mild conditions to avoid the decarboxylation of the malonic acid monoanilide intermediate.

An alternative way to analogues of avenanthramides and their antiradical activity

Abstract: The paper is devoted to the synthesis of arylidene malonic acid monoanilides and cinnamoyl anilines by condensation of malonic acid monoanilides with aromatic aldehydes. The presented synthetic route applies simple, cheap, and commercially available aromatic aldehydes and amines, thus overcoming traditional schemes, which involve derivatives of hydroxycinnamic acids. Besides, a mild and effective pyridine-mediated decarboxylation of carboxylic group at Csp2 in arylidene malonic acid monoanilides leading to cinnamoyl anilines is presented. The structures of obtained selected arylidene derivatives were approved additionally by X-ray analysis. The antiradical properties (2,2-diphenyl-1-picrylhydrazyl and galvinoxyl tests) and structure–activity relationships of the synthesized compounds were studied. Graphical abstract: [Figure not available: see fulltext.].

OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS

Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.

Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox

Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure-plasma stability relationships in these series and to identify which enzyme(s) and which pharmacophores are critical for plasma stability. Arylesterases and carboxylesterases were identified as the main metabolic enzymes for hydroxamic acids. Finally, we suggest structural features to be introduced or removed to improve stability. This work thus provides the first medicinal chemistry toolbox (experimental procedures and structural guidance) to assess and control the plasma stability of hydroxamic acids and realize their full potential as in vivo pharmacological probes and therapeutic agents. This study is particularly relevant to preclinical development as it allows obtaining compounds equally stable in human and rodent models.

Ambient Decarboxylative Arylation of Malonate Half-Esters via Oxidative Catalysis

We report decarboxylative carbonyl α-arylation by coupling of arylboron nucleophiles with malonic acid derivatives. This process is enabled by the merger of aerobic oxidative Cu catalysis with decarboxylative enolate interception reminiscent of malonyl-CoA reactivity in polyketide biosynthesis. This method enables the synthesis of monoaryl acetate derivatives containing electrophilic functional groups that are incompatible with existing α-arylation reactivity paradigms. The utility of the reaction is demonstrated in drug intermediate synthesis and late-stage functionalization.

Compound of bisamide structure and preparing method and application thereof

The invention discloses a compound of a bisamide structure in the technical field of agricultural chemistry and a preparing method and application thereof. The preparing method includes the steps that monomethyl malonate acyl chloride is used as a raw material and reacts with arylamine in anhydrous dichloromethane to obtain an intermediate product III; the intermediate product III reacts with lithium hydroxide and then reacts with oxalyl chloride in tetrahydrofuran to obtain an intermediate product IV; 2,6-dimethylaniline is used as a raw material and reacts with 2-methyl bromopropionate to obtain an intermediate product VI; finally the intermediate product IV and the intermediate product VI react in a methylbenzene solution to obtain the compound of the bisamide structure shown in the final product I. The compound and a preparation have good bactericidal activity, have a good growth inhibiting function on phytophthora capsici, alternaria solani, rhizoctonia solani, cotton rhizoctonia solani, phytophthora infestans, and botrytis cinerea and have high pesticide research value.

Rational design of the first furoquinolinol based molecular systems for easy detection of Cu2+ with potential applications in the area of membrane sensing

Two molecular probes based on the furoquinolinol (FQ) framework have been rationally designed for the rapid detection and trace level quantification of Cu2+ in organic and semi-aqueous mediums. Synthesized FQs were extensively examined for their Cu2+ sensing abilities by UV-vis/fluorescence experiments, NMR titrations and DFT based calculations. Higher binding constant [2.11 × 104 M-1 (FQ1) and 1.87 × 104 M-1 (FQ2)], low detection limit [1.52 × 10-7 M (FQ1) and 2.13 × 10-7 M (FQ2)], high selectivity, fast response, wide operational pH range, and repeated usability are some of the salient features of the reported sensors. Furthermore, these compounds (FQs) retained their metal detection abilities in thin PVC membranes.