94-41-7 Usage
Description
Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids.They show antibacterial, antifungal, antitumor and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activities. Chalcones are also intermediates in the Auwers synthesis of flavones.
Chemical Properties
light yellow powder
Uses
Different sources of media describe the Uses of 94-41-7 differently. You can refer to the following data:
1. 1,3-Diphenyl-2-propenone was used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines.
2. Chalcone is used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines. It also inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase.
Definition
ChEBI: A member of the class of chalcones that is acetophenone in which one of the methyl hydrogens has been replaced by a benzylidene group.
Preparation
Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones.Chalcones can be prepared by an aldol condensation between a benzaldehyde and an acetophenone in the presence of sodium hydroxide as a catalyst.This reaction has been found to work without any solvent at all - a solid-state reaction. The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).
Biological Activity
1,3-Diphenyl-2-propenone (chalcone) inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase. It is an inhibitor of Plasmodium falciparum cyclin-dependent protein kinases.
Biochem/physiol Actions
1,3-Diphenyl-2-propenone (chalcone) inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase. It is an inhibitor of Plasmodium falciparum cyclin-dependent protein kinases.
Safety Profile
Poison by intravenous
route. See also KETONES. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Purification Methods
Crystallise it from EtOH by warming to 50o (about 5mL/g), iso-octane, or toluene/pet ether, or recrystallise it from MeOH, and then twice from hexane. SKIN IRRITANT. [Beilstein 7 IV 1658.]
Check Digit Verification of cas no
The CAS Registry Mumber 94-41-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 4 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 94-41:
(4*9)+(3*4)+(2*4)+(1*1)=57
57 % 10 = 7
So 94-41-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11-
94-41-7Relevant articles and documents
Silver-Catalyzed Intramolecular C-2 Selective Acylation of Indoles with Aldehydes: An Atom-Economical Entry to Indole-Indolone Scaffolds
Wang, Xiaoxia,Li, Zhongfeng,Cao, Shengli,Rao, Honghua
, p. 2059 - 2065 (2016)
A direct annulation reaction of N-(2-formylaryl)indoles has been developed, which can provide a new entry to biologically and medicinally important indole-indolone scaffolds via a silver-catalyzed direct oxidative coupling between aldehyde C H and sp2C H bonds for the first time. Remarkably, this strategy displayed excellent functional group compatibilities, thereby suggesting its wide potential for applications in developing and synthesizing new drug-like compounds containing indole-indolone frameworks. (Figure presented.) .
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Egger,Schloegl
, p. 398,404 (1964)
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Arnould,J.C.,Pete,J.P.
, p. 2459 - 2462 (1975)
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The kinetics and mechanism of reactions of cis- and trans-chalcones with amines.
Menger,Smith
, p. 4211 - 4216 (1969)
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Lutz,Jordan
, p. 40,90 (1950)
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Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles
Abinaya, R.,Balasubramaniam, K. K.,Baskar, B.,Divya, P.,Mani Rahulan, K.,Rahman, Abdul,Sridhar, R.,Srinath, S.
, p. 5990 - 6007 (2021/08/24)
Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.
Iron-Catalyzed Alkyne-Based Multicomponent Synthesis of Pyrimidines under Air
Chakraborty, Gargi,Guin, Amit Kumar,Mondal, Rakesh,Paul, Nanda D.,Sarkar, Susmita
, p. 13186 - 13197 (2021/10/01)
An iron-catalyzed sustainable, economically affordable, and eco-friendly synthetic protocol for the construction of various trisubstituted pyrimidines is described. A wide range of trisubstituted pyrimidines were prepared using a well-defined, easy to prepare, bench-stable, and phosphine-free iron catalyst featuring a redox-noninnocent tridentate arylazo pincer under comparatively mild aerobic conditions via dehydrogenative functionalization of alcohols with alkynes and amidines.
