495-86-3

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure, including the benzodioxole ring and propenamide functional group, may contribute to the development of new drugs with specific therapeutic properties.
Used in Drug Discovery:
(2E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide is used as a potential lead compound in drug discovery. Its structural features may allow for the design and optimization of new therapeutic agents targeting specific biological pathways or receptors.
Further research and investigation are needed to fully understand the properties and potential uses of (2E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide in various applications.

Upstream product

• 96249-87-5 3-benzo[1,3]dioxol-5-yl-acryloyl chloride 
• 78-81-9 isobutylamine 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 74058-80-3 3-(3,4-methylenedioxycinnamoyl)-1,3-thiazolidine-2-thione 
• 120-57-0 piperonal 
• 73818-55-0 Bestmann ylide 
• 96249-87-5 (E)-3-(1,3-benzodioxol-5-yl)acryloyl chloride 
• 2033-24-1 cycl-isopropylidene malonate 

Downstream Products

• 120-57-0 piperonal 
• 94-53-1 Piperonylic acid 

Relevant academic research and scientific papers

Rapid access to cinnamamides and piper amides: Via three component coupling of arylaldehydes, amines, and Meldrum's acid

A practical method for the synthesis of cinnamamides and piper amides via a conceptually novel three component reaction of aldehydes, amines and Meldrum's acid has been reported. The reaction proceeds under operationally simple conditions without the aid of coupling reagents, oxidants, or catalysts, which are essential for the preparation of cinnamamides/piper amides via known methods. The formation of undesired chemical wastes that generally originate from the use of coupling reagents, oxidants, or catalysts has been avoided to make this reaction more atom economical.

Mild, Metal-Free and Protection-Free Transamidation of N-Acyl-2-piperidones to Amino Acids, Amino Alcohols and Aliphatic Amines and Esterification of N-Acyl-2-piperidones

Amides are indispensable building blocks of biological systems, pharmaceuticals, and materials. We report a highly selective method for the synthesis of amides via transamidation process. Transamidation of N-acyl-2-piperidones with a broad range of amines is demonstrated under exceedingly mild and metal-free reaction condition that relies on the amide bond twist to weaken the amidic resonance. Transamidation proceeds under the neat condition at room temperature, in short reaction times (30–90 min) with good yields. Considerable variation is tolerated with both amine and imide substrates. Of note, amines bearing carboxylic acids (glycine and serine) and hydroxyl groups (dopamine, tyramine, etc.) are well tolerated which are otherwise problematic under the metal-catalyzed protocol. Our current method is applicable for transamidation of both alkyl and aryl-N-acyl-2-piperidones. The practical value of the method is highlighted by the synthesis of four natural product amide alkaloids in high yields under mild reaction conditions. In the absence of nucleophilic amines, N-acyl-2-piperidones undergoes esterification with EtOH at elevated temperature. Single crystal X-ray analysis of an N-acyl-2-piperidone shows amide bond twist, τ = –20.39° and pyramidalization, χN = –11.73°. This weakens the amidic conjugation and might be the factor controlling the reactivity and selectivity of these imides. We envision that the N-acyl-2-piperidone scaffold would be useful in the synthesis of pharmaceuticals and materials.

Synthesis of Analogs of Trans-Fagaramide and Their Cytotoxic Activity

A series of 30 compounds were synthetized inspired by active trans-fagaramide structure skeleton. On this synthetic platform, 18 compounds were achieved via Knoevenagel condensation using maleic acid and piperonal, followed by peptide coupling with various amines, giving an average yield of 54%. Subsequently, nine compounds were obtained by palladium-mediated Heck coupling with an average yield of 79%. In addition, cytotoxic activity was evaluated against cardiomyoblast H9c2, breast adenocarcinoma MCF7, hepatocellular carcinoma HepG2, and glioblastoma U-87 cells. The results revealed two aryl halogen-substituted compounds moderately active against H9c2 and MCF7 with IC50 values > 50 μM. One functionalized coumarin showed inhibitory activity against H9c2 (IC50 > 50 μM). In contrast, p-aminophenyl-β-monosubstituted trans-fagaramide was found to inhibit MCF7 (IC50 > 50 μM) without showing toxicity against H9c2 cells.

In vitro TRPV1 activity of piperine derived amides

A series of natural and synthetic piperine amides were evaluated for activity on the human TRPV1 expressed in HEK293 cells. The agonistic effect of piperine amides was mainly dependent on the length of the carbon chain. Structural changes of double bonds and stereochemistry in the aliphatic chain of these compounds did not change their potency or efficacy, indicating that increased rigidity or planarity of the piperine structure does not affect the activity. The opening of the methylenedioxy ring or changes in the heterocyclic ring of the piperine molecule reduced or abolished activity. Furthermore, inactive compounds did not display functional antagonistic activity.

Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

Selective formation of (E)-α,β-unsaturated amides by intermolecular three-component reaction between aldehydes, amines (1° or 2°) and ketenylidenetriphenylphosphorane (Ph3P=C=C=O) is described. Natural amides such as fagaramide and piperines could be prepared from immediately available educts. The method is shown to be extendable to the preparation of thioesters from thiols and aldehydes.

Monitored Aminolysis of 3-Acyl-1,3-thiazolidine-2-thiones: Synthesis of Amides and Amide Alkaloids

A functional heterocycle, 3-acyl-1,3-thiazolidine-2-thione has been shown to be effective as an acylating reagent for the amino group.ATT (1) was readily prepared by several methods, and reacted with various amino compounds in CHCl3, CH2Cl2, THF, EtOH, THF-H2O, or sulfolane to afford the corresponding amides, 2a-w and 3-10 in very high yields within a short time.This reagent exhibits high chemo-selectivity.Its reaction with the diamines 13 and 15 and the triamine 29, which include a primary amino group(s) and a secondary amino group, gave the products acylated only at the primary amino group(s), 14, 16, and 30, respectively, in high yields.Aminoalcohols and aminophenols were chemoselectively converted into acylaminoalcohols and acylaminophenols, respectively, by ATT (1).By utilizing this method, several amide alkaloids (26, 28, 30, and 34) were efficiently synthesized.This new aminolysis can be monitored by the disappearance of the yellow color of the starting materials, ATT (1); it is remarkably characteristic of this reaction. Keywords - monitored aminolysis; 3-acyl-1,3-thiazolidine-2-thione; high chemo-selectivity; amide synthesis; fagaramide; dolicotheline; spermidine; maytenine; N-ferulyltryptamine

MONITORED AMINOLYSIS OF 3-ACYLTHIAZOLIDINE-2-THIONE : A NEW CONVENIENT SYNTHESIS OF AMIDE

3-Acylthiazolidine-2-thiones (1) were easily prepared and they were treated with several amines in dichloromethane to give amides 4 in very high yields within a short time.Aminoalcohols and aminophenols were selectively converted into acylaminoalcohols and acylaminophenols, respectively, by this reaction.One can monitor the reaction by disappearance of the yellow color of the starting material 1.Some amide alkaloids (15-18) have effectively been synthesized.