102692-40-0

Basic information

• Product Name: 2-Propen-1-one, 1-(4-methylphenyl)-3-(4-nitrophenyl)-, (E)-
• Synonyms: (E)-1-(4-METHYLPHENYL)-3-(4-NITROPHENYL)-2-PROPEN-1-ONE;(2E)-1-(4-methylphenyl)-3-(4-nitrophenyl)prop-2-en-1-one
• CAS NO: 102692-40-0
• Molecular Formula: C₁₆H₁₃NO₃
• Molecular Weight: 267.28
• Mol File: 102692-40-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propen-1-one, 1-(4-methylphenyl)-3-(4-nitrophenyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propen-1-one, 1-(4-methylphenyl)-3-(4-nitrophenyl)-, (E)-(102692-40-0)
• EPA Substance Registry System: 2-Propen-1-one, 1-(4-methylphenyl)-3-(4-nitrophenyl)-, (E)-(102692-40-0)

Safety Data

• Hazardous Substances Data: 102692-40-0(Hazardous Substances Data)

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 122-00-9 para-methylacetophenone 
• 2096-86-8 p-Tolylaceton 
• 20691-75-2 1-p-tolyl-2-(triphenyl-λ⁵-arsanylidene)-ethanone 
• 619-41-0 4-(bromoacetyl)toluene 

Downstream Products

• 27547-04-2 (3-(4-nitrophenyl)oxiran-2-yl)(p-tolyl)methanone 
• 1772-39-0 6-nitro-2-(4-nitrophenyl)-1H-benzo[d]imidazole 
• 104-03-0 4-nitrobenzeneacetic acid 
• 99-94-5 p-Toluic acid 
• 57026-76-3 1-(4-Nitro-phenyl)-3-p-tolyl-propane-1,3-dione 
• 93850-87-4 [(4S,5R)-2,2-Dimethyl-5-(4-nitro-phenyl)-[1,3]dioxolan-4-yl]-p-tolyl-methanone 
• 1197386-04-1 2-(p-tolylthio)-4-(4-nitrophenyl)-6-p-tolylpyridine-3-carbonitrile 

Relevant articles and documents

Monofunctionalized 1,3,5,7-tetraarylazaBODIPYs and their application in the synthesis of AzaBODIPY based conjugates

A series of monofunctionalized 1,3,5,7-tetraarylazaBODIPYs containing functional groups such as p-hydroxymethyl phenyl, p-hydroxyphenyl, p-cyanophenyl, p-nitrophenyl, and p-formylphenyl groups at the 1-position of the azaBODIPY core were synthesized by mi

Antimicrobial and cytotoxicity potential of acetamido, amino and nitrochalcones

Background: Chalcones constitute one of the major classes of natural products belonging to the flavonoid family, and they have been reported as having a range of important therapeutic activities, including some chalcones are effective as antimicrobial agents. Currently, the search for new structures with antimicrobial activity has been intensified due to the emergence of many strains resistant to antibiotics currently used to treat infectious diseases. Method: 3 chalcone series (amino, acetamido and nitrochalcones) were prepared (23 compounds) and evaluated for their antimicrobial and cytotoxic potential. The effects of substituents on their respective activities also was evaluated. Results & Conclusion: The results showed that 4 aminochalcones (2, 4, 8, 9), 3 acetoamidochalcones (10, 14, 18) and 3 nitrochalcones (20, 22, 23), exhibited antifungal effects. The aminochalcones were more toxic than the acetamidochalcones, while the nitrochalcones did not present any toxic effect. It was verified that there seems to be structure-activity correlation in some electron-donating and withdrawing substituents groups in rings A and B of the synthetized chalcone analogues and its antifungal and cytotoxic activity. Georg Thieme Verlag KG Stuttgart New York.

Lewis acid catalyst system for Claisen-Schmidt reaction under solvent free condition

Ca(OTf)2 in combination with NBu4.BF4 was established to function as an efficient catalyst system for one-pot Claisen-Schmidt condensation under neat conditions. Substituted acetophenones and benzaldehydes were coupled in situ to afford their corresponding chalcones in excellent yields. The method, with a broad range of substrate tolerance and mild operational conditions can produce assorted chalcone derivatives in moderate to high yields from easily accessible starting materials.

Iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate: Synthesis of 3,5-disubstituted 1H-pyrazoles

We have developed an iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate. Various 3,5-disubstituted 1H-pyrazoles were obtained in good to excellent yields. This method offers several advantages, including room-temperature conditions, short reaction time, high yields, simple work-up procedure, and use of air as an oxidant. The catalyst can be recovered and reused five times without loss of activity.

Monoamine Oxidase Inhibitory Activity: Methyl- versus Chlorochalcone Derivatives

Numerous studies have shown that chalcones are promising scaffolds for the development of new monoamine oxidase-B (MAO-B) inhibitors. As a continuation of our ongoing research into the development of reversible human MAO-B (hMAO-B) inhibitors, two series

Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach

Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.

A multicomponent pathway-inspired regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles via [3+2] cycloaddition reaction

A copper catalyzed regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles using a novel three-component coupled domino reaction of aldehydes, ketones and alkyl isocyanoacetates is reported. This transformation proceeds through the formation of a chalcone followed by a [3+2] cycloaddition reaction to obtain α-cuprioisocyanide, a cyclic organocopper intermediate, which on copper-hydrogen exchange followed by oxidation exclusively offers 2,3,4-trisubstituted 1H-pyrrole.

Electronically tunable anion-π interactions in pyrylium complexes: Experimental and theoretical studies

Noncovalent interactions of anions with electron-deficient aromatic rings that have been studied so far involve non-heteroaromatic or nitrogen-based heteroaromatic systems. Here we report the first case of an organic oxygenated aromatic system, in particular the tri-aryl-pyrylium tetrafluoroborate system, for which noncovalent anion-π interactions of the pyrylium cation with the tetrafluoroborate anion have been experimentally detected and demonstrated by means of 19F NMR spectroscopy in solution. A series of pyrylium tetrafluoroborate salts were synthesized in the presence of BF 3·Et2O, by direct reaction of 4-substituted benzaldehydes with 4-substituted acetophenones or via the previously obtained chalcone of the less reactive ketone. Correlations of 19F NMR chemical shifts of tetrafluoroborate anion for most of the synthesized tri-arylpyrylium tetrafluoroborate complexes with both the pyrylium cation molecular weight and the standard substituent Hammett constants, demonstrate anion-π+ interaction to act between the polyatomic anion BF 4- and the pyrylium aromatic system. DFT calculations reveal that an additional (C-H)+-anion hydrogen bond involving the H(5) of pyrylium ring exists for these fluorescent dyes that show a tunable cup-to-cap shape cavity. The strong fluorescence emission observed for some representative pyrylium tetrafluoroborates described herein, makes them a promising class of tunable emission wavelength dyes for laser technology applications. the Partner Organisations 2014.

Effects of structural and electronic characteristics of chalcones on the activation of peroxisome proliferator-activated receptor gamma

Chalcones share some structural similarities with GW-1929, a highly-selective and potent agonist for peroxisome proliferator-activated receptor-gamma (PPARγ). In this study, we tested 53 structurally diverse chalcones to identify characteristics essential for PPARγ activation in a GAL4-based transactivation assay. This screen identified several novel chalcone agonists of PPARγ. Our results indicate that chalcones with an electron rich group or sterically large groups such as naphthyl on the carbonyl side tend to activate PPARγ. The absence of any strict structural or electronic requirements suggests that the flexibility of the PPARγ ligand binding pocket may allow binding of diverse chalcones with some preference for a slightly larger electron-rich group on the carbonyl side. We predict that further structure-activity relationship studies on chalcones with naphthalene or electron-rich groups near the carbonyl moiety will lead to the development of more potent PPARγ agonists.

Syntheses and biological activity of chalcones-imidazole derivatives

A number of novel 13-membered chalcone-imidazole derivatives were prepared and have been synthesized and characterized by IR, 1H NMR, 13C NMR and elemental analysis, the results conformed well to expected structures. Substituted acetophenones and benzaldehydes were condensed using the Claisen-Schmidt base-catalyzed aldol condensation. Methyl on the aromatic ring of chalcones was brominated by NBS, and then the resulting mixture was reacted with imidazole to get the target compound. Several chalcones showed in vitro antibacterial activity against Gram-bacterial. The results showed that these are potential antibacterial compounds.