18096-70-3

Basic information

• Product Name: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one
• Synonyms: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one;(E)-3-dimethylamino-1-(4-methoxyphenyl)prop-2-en-1-one;11C-002;MLS000546311;SMR000169481;ZINC00126223
• CAS NO: 18096-70-3
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.253
• Mol File: 18096-70-3.mol

Chemical Properties

• Melting Point: 92-95℃
• Appearance: /
• CAS DataBase Reference: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one(18096-70-3)
• EPA Substance Registry System: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one(18096-70-3)

Safety Data

• Hazardous Substances Data: 18096-70-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one is used as a catalyst in the synthesis of pharmaceuticals for its ability to facilitate key chemical reactions, such as acylation and esterification, which are crucial in the production of various drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one serves as a catalyst for the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural products that require precise chemical transformations.
Used in Organic Synthesis:
3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one is utilized as a reagent in organic synthesis for its capacity to act as an effective catalyst, enabling the formation of new chemical bonds and the creation of a wide range of organic compounds.

Upstream product

• 506-59-2 N,N-dimethylammonium chloride 
• 34933-41-0 sodium salt of p-methoxybenzoylacetaldehyde 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 98-86-2 acetophenone 
• 20353-93-9 <3-(dimethylamino)-2-azaprop-2-en-1-ylidene> dimethylammonium chloride 
• 20353-93-9 Gold's reagent 

Downstream Products

• 858935-67-8 methyl 4-(p-methoxybenzoyl)-3-methylpyrrole-2-carboxylate 
• 1166821-59-5 1-methyl-4-(4-methylphenyl)-5-(4-methoxyphenyl)methanone-yl-3,4-dihydropyrimidine-2(1H)-one 
• 1166821-50-6 4-(4-chlorophenyl)-5-(4-methoxylphenyl)methanone-yl-3,4-dihydropyrimidine-2(1H)-one 
• 1166821-62-0 1-methyl-4phenyl-5-(4-methoxyphenyl)methanone-yl-3,4-dihydropyrimidine-2(1H)-thione 
• 1166821-49-3 4-(4-Methoxyphenyl)-5-(4-methoxylphenyl)methanone-yl-3,4-dihydropyrimidine-2(1H)-one 
• 1166821-57-3 4-ethyl-5-phenylmethanone-yl-3,4-dihydropyrimidine-2(1H)-one 
• 1166821-58-4 4-propyl-5-phenylmethanone-yl-3,4-dihydropyrimidine-2(1H)-one 
• 1276536-43-6 C₁₈H₁₉NO₄ 
• 59838-66-3 2-(4-methoxyphenyl)-7,8-dihydroquinolin-5(6H)-one 
• 1477476-63-3 C₁₇H₁₈N₂O₂ 
• 1477476-40-6 5-methoxy-2-(5-(methoxyimino)-5,6,7,8-tetrahydroquinolin-2-yl)phenyl acetate 
• 1477476-00-8 5-methoxy-2-(5-oxo-5,6,7,8-tetrahydroquinolin-2-yl)phenyl acetate 
• 1477476-07-5 2-(7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinolin-2-yl)-5-methoxyphenyl acetate 
• 1477476-14-4 2-(6,6-dimethyl-5-oxo-5,6,7,8-tetrahydroquinolin-2-yl)-5-methoxylphenyl acetate 

Relevant articles and documents

DDQ-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene

An efficient 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene is developed. It provides a variety of α-alkenylated 1,3-dicarbonyl compounds in moderate to good yields under mild conditions.

ANTIVIRAL COMPOUNDS

A compound can include the structure of Formula 1, derivative thereof, prodrug thereof, salt thereof, stereoisomer thereof, tautomer thereof, polymorph thereof, or solvate thereof, or having any chirality at any chiral center: R1 includes a hyd

Discovery of highly potent tubulin polymerization inhibitors: Design, synthesis, and structure-activity relationships of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines

By removing 5-methyl and 6-acetyl groups in our previously reported compound 3, we designed a series of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine derivatives as potential tubulin polymerization inhibitors. Among them, compound 5e displayed low nanomolar antiproliferative efficacy on HeLa cells which was 166-fold higher than the lead analogue 3. Interestingly, 5e displayed significant selectivity in inhibiting cancer cells over HEK-293 (normal human embryonic kidney cells). In addition, 5e dose-dependently arrested HeLa in G2/M phase through the alterations of the expression levels of p-cdc2 and cyclin B1, and caused HeLa cells apoptosis by regulation of expressions of cleaved PARP. Further evidence demonstrated that 5e effectively inhibited tubulin polymerization and was 3-fold more powerful than positive control CA-4. Moreover, molecular docking analysis indicated that 5e overlapped well with CA-4 in the colchicine-binding site. These studies demonstrated that 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine skeleton might be used as the leading unit to develop novel tubulin polymerization inhibitors as potential anticancer agents.

Efficient synthesis, structure elucidation, and anti-parasitic activities of novel quinolinyl β–enaminones

In the present study, a novel series of side chain-modified quinoline β-enaminones were synthesized in good-to-excellent yields. The structures of all the synthesized compounds have been established with the help of spectral and analytical data and also b

An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes asC4units

An efficient method has been described to synthesize dicarbonyl functionalized 1,3-dienes by cleaving the CC bond of enaminones with cyclopropenes in the presence of a rhodium catalyst. The acetate-substituted cyclopropenes are judiciously chosen as standardC4units of 1,3-diene precursors. The reactions are believed to undergo a unique cutting and insertion process, involving a CC bond cleavage of the enaminone and insertion of a newC(sp2) source with the formation of two C-C single bonds. A broad range of substrates can be used to synthesize the corresponding 1,3-dienes under very mild reaction conditions, including low catalyst-loading, ambient temperature, and a neutral reaction solvent.

Structure-Based Discovery of Pyrimidine Aminobenzene Derivatives as Potent Oral Reversal Agents against P-gp- And BCRP-Mediated Multidrug Resistance

Overexpression of ATP binding cassette (ABC) transporters, including P-glycoprotein (P-gp) and breast cancer resistance protein (BCRP), is an important factor leading to multidrug resistance (MDR) in cancer treatments. Three subclasses of dual inhibitors of P-gp and BCRP were designed based on the active moieties of BCRP inhibitors, tyrosine kinase inhibitors, and P-gp inhibitors, of which compound 21 possessed low cytotoxicity, high reversal potency, and good lipid distribution coefficient. 21 also increased the accumulation of Adriamycin (ADM) and Mitoxantrone (MX), blocked Rh123 efflux, and made no change in the protein expression of P-gp and BCRP. Importantly, coadministration of 21 can significantly improve the oral bioavailability of paclitaxel (PTX). It was also demonstrated that 21 significantly inhibited the growth of K562/A02 xenograft tumors by increasing the sensitivity of ADM in vivo. In summary, 21 has the potential to overcome MDR caused by P-gp and BCRP and to improve the oral bioavailability of PTX.

One-Pot Synthesis of Symmetrical and Asymmetrical 3-Amino Diynes via Cu(I)-Catalyzed Reaction of Enaminones with Terminal Alkynes

An economical and efficient protocol for the direct construction of amino skipped diynes through the Cu(I)-catalyzed reaction of enaminones and terminal alkynes has been described. Different kinds of symmetrical and asymmetrical 3-amino diynes could be ob

Sulfonamide/sulfamate switch with a series of piperazinylureido derivatives: Synthesis, kinetic and in silico evaluation as carbonic anhydrase isoforms I, II, IV, and IX inhibitors

We report here a thorough structure-activity relationship (SAR) with piperazinylureido sulfamates as inhibitors of human (h) carbonic anhydrase (CA, EC 4.2.1.1). A SAR investigation over the structure of reported anti-cancer zinc-binder CAIs such as SLC-0

Stereoselective synthesis of trifluoromethyl-substituted 2: H -furan-amines from enaminones

A straightforward strategy for synthesis of highly functionalized trifluoromethyl 2H-furans is described. The copper catalyzed method relies on a cascade cyclic reaction between enaminones and N-tosylhydrazones. This method allows the synthesis of 2-amino

Modification on the 1,2-dihydro-2-oxo-pyridine-3-carboxamide core to obtain multi-target modulators of endocannabinoid system

Several preclinical evidence indicate that the modulation of the endocannabinoid system (ECS) represents a promising therapeutic approach for different diseases. However, only few modulators of this system have reached so far an advanced stage of clinical development, mainly due to limited efficacy and CB1 receptor-dependent side effects. Those limitations might be overcome by multi-target compounds that exert pro-cannabinoid activities through the modulation of two or more targets in the ECS. This approach can offer a safer and more effective pharmacological strategy as compared to the modulation of a single target. In this work, we report the synthesis and biological characterization of new 6-aryl-1,2-dihydro-2-oxo-pyridine-3-carboxamide derivatives. Our results identified several compounds exhibiting interesting multi-target profiles within the ECS. In particular, compound B1 showed moderate-to-high affinity for cannabinoid receptors (Ki CB1R = 304 nM, partial agonist, Ki CB2R = 3.1 nM, inverse agonist) and a potent inhibition of AEA uptake (IC50 = 62 nM) with moderate inhibition of FAAH (IC50 = 2.9 μM). The corresponding 2-alkoxypyridine analogue B14 exhibited significant inhibitor activity on both FAAH (IC50 = 69 nM) and AEA uptake (IC50 = 76 nM) without significantly binding to both cannabinoid receptor subtypes. Molecular docking analysis was carried out on the three-dimensional structures of CB1R and CB2R and of FAAH to rationalize the structure-activity relationships of this series of compounds.