- Rapid abnormal [3+2]-cycloaddition of isatinN,N′-cyclic azomethine imine 1,3-dipoles with chalcones
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The rapid synthesis of novel dicyclic spiropyrrolidine was reported, using [3+2]-cycloaddition of isatinN,N′-cyclic azomethine imine 1,3-dipoles, generated from the condensation of substituted isatins and pyrazolidones, with chalcones in 2-5 min. The dicy
- Yue, Guizhou,Dou, Zhengjie,Zhou, Zexi,Zhang, Li,Feng, Juhua,Chen, Huabao,Yin, Zhongqiong,Song, Xu,Liang, Xiaoxia,Wang, Xianxiang,Rao, Hanbing,Lu, Cuifen
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supporting information
p. 8813 - 8817
(2020/06/08)
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- Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
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A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.
- Jeong, Eun Jeong,Lee, In-Sook Han
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p. 668 - 673
(2019/07/12)
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- Effect of solvent polarity on the photophysical properties of chalcone derivatives
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The absorption and fluorescence characteristics of (E)-3-(furan-2-yl)-1-(4-nitrophenyl)prop-2-en-1-one (FNPO), (E)-1-(4-aminophenyl)-3-(furan-2-yl)prop-2-en-1-one (AFPO) and (E)-3-(furan-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (FHPO) were recorded in eig
- Kumari, Rekha,Varghese, Anitha,George, Louis,Sudhakar
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p. 24204 - 24214
(2017/07/11)
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- Synthesis, cyclooxygenase inhibition and anti-inflammatory evaluation of new 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives possessing methanesulphonyl pharmacophore
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A new series of 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives 13a–p were synthesized via aldol condensation of 3/4-nitroacetophenones with appropriately substituted aldehydes followed by cyclization of the formed chalcones with 4-methanesulfonylphenylhydrazine hydrochloride. All the synthesized compounds were evaluated for their cyclooxygenase (COX) inhibition, anti-inflammatory activity and ulcerogenic liability. All compounds were more potent inhibitors for COX-2 than COX-1. While most compounds showed good anti-inflammatory activity, compounds 13d, 13f, 13k and 13o were the most potent derivatives (ED50 = 66.5, 73.4, 79.8 and 70.5 μmol/kg, respectively) in comparison with celecoxib (ED50 = 68.1 μmol/kg). Compounds 13d, 13f, 13k and 13o (ulcer index = 3.89, 4.86, 4.96 and 3.92, respectively) were 4–6 folds less ulcerogenic than aspirin (ulcer index = 22.75) and showed approximately ulceration effect similar to celecoxib (ulcer index = 3.35). In addition, molecular docking studies were performed for compounds 13d, 13f, 13k and 13o inside COX-2 active site which showed acceptable binding interactions (affinity in kcal/mol ?2.1774, ?6.9498) in comparison with celecoxib (affinity in kcal/mol ?6.5330).
- Abdellatif, Khaled R. A.,Elsaady, Mohammed T.,Abdel-Aziz, Salah A.,Abusabaa, Ahmed H. A.
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p. 1545 - 1555
(2016/10/09)
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- Synthesis and anti-inflammatory evaluation of new 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives possessing an aminosulphonyl pharmacophore
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A novel series of 2-pyrazoline derivatives 13a-l was synthesized via aldol condensation of 4-substituted acetophenones with appropriately substituted aldehydes followed by cyclization of the formed chalcones with 4-hydrazinobenzenesulfonamide hydrochlorid
- Abdellatif, Khaled R. A.,Abdelgawad, Mohamed A.,Elshemy, Heba A. H.,Alsayed, Shahinda S. R.,Kamel, Gehan
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p. 1932 - 1942
(2015/11/24)
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- Iron-catalyzed aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines
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A simple and high yielding method for the synthesis of tri-substituted pyrazoles via iron(III) catalyzed aerobic oxidative aromatization of pyrazolines has been reported. The process demonstrates a variety of functional group tolerance.
- Ananthnag, Guddekoppa S.,Adhikari, Adithya,Balakrishna, Maravanji S.
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p. 240 - 243
(2013/12/04)
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- Chalcones as promising pesticidal agents against diamondback moth (Plutella xylostella): Microwave-assisted synthesis and structure-activity relationship
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A series of chalcones (A-CH=CH-CO-B) were synthesized under microwave irradiation, and for the first time their pesticidal activity against diamondback moth (Plutella xylostella) was evaluated to identify the promising lead structures. The structure-activity relationship (SAR) analysis revealed that electron-withdrawing substituents on ring A of chalcone provided good pesticidal agents, whereas, ring B can bear either electron-withdrawing or electron-releasing substituents. Moreover, compound 22 having para-Cl substitution on ring A as well on ring B showed maximum activity with LC 50 value of 170.24 μg mL-1. Springer Science+Business Media, LLC 2011.
- Kumar, Rakesh,Sharma, Prabha,Shard, Amit,Tewary, Dhananjay Kumar,Nadda, Gireesh,Sinha, Arun Kumar
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experimental part
p. 922 - 931
(2012/08/14)
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- Synthesis and anti-bacterial activity of some heterocyclic chalcone derivatives bearing thiofuran, furan, and quinoline moieties
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36 Novel heterocyclic chalcone derivatives were synthesized and tested for their anti-bacterial activity. Some compounds presented good anti-microbial activities against Gram-positive bacteria (including the multidrug-resistant clinical isolates). This cl
- Zheng, Chang-Ji,Jiang, Sheng-Ming,Chen, Zhen-Hua,Ye, Bai-Jun,Piao, Hu-Ri
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experimental part
p. 689 - 695
(2012/06/01)
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- Design, synthesis, and bioactivities screening of a diaryl ketone-inspired pesticide molecular library as derived from natural products
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Three natural products, 1,5-diphenylpentan-1-one, 1,5-diphenylpent-2-en-1-one, and 3-hydroxy-1,5-diphenylpentan-1-one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as 'pharmacophores', a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)-1-(2,4-dichlorophenyl)-3-(furan-2-yl)- -prop-2-en-1-one (III2) was 1.20mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.
- Zhang, Hong,Jin, Hong,Ji, Lan-Zhu,Tao, Ke,Liu, Wei,Zhao, Hao-Yu,Hou, Tai-Ping
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experimental part
p. 94 - 100
(2012/06/01)
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- Screening of biological activities of a series of chalcone derivatives against human pathogenic microorganisms
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In an effort to develop new antimicrobial agents, a series of chalcone derivatives, 3-60, were prepared by Claisen-Schmidt condensation of appropriate acetophenones and 2-furyl methyl ketones with appropriate aromatic aldehydes, furfural, and thiophene-2-carbaldehyde in an aqueous solution of NaOH and EtOH at room temperature. The synthesized compounds were characterized by means of their IR- and NMR-spectral data, and elemental analysis. All compounds were tested for their antibacterial and antifungal activities by the disc diffusion method. For the most active compounds, also minimum inhibitory concentrations (MICs) were determined.
- Karaman, Isa,Gezegen, Hayreddin,Guerdere, M. Burcu,Dingil, Alparslan,Ceylan, Mustafa
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experimental part
p. 400 - 408
(2010/09/04)
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- Reinvestigation of structure-activity relationship of methoxylated chalcones as antimalarials: Synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone
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We have examined the antimalarial structure-activity relationship of a series of methoxylated chalcones (A-CHCH-CO-B) against Plasmodium falciparum (3D7 strain) using fluorescence-based SYBR Green assay. Our study has revealed that electron releasing methoxy groups on ring A and electron withdrawing groups on ring B increases antimalarial potency while the positional interchange of these groups causes a decrease. In particular, 2,4,5-trimethoxy substitution pattern at ring A provided potent analogues which were easily derived from abundantly available natural β-asarone rich Acorus calamus oil. Cytotoxic evaluation indicated that the most active compounds 27 (IC50: 1.8 μM) and 26 (IC50: 2 μM) were also relatively non-toxic. Furthermore, compound 12 showed excellent resistance index of 1.1 against chloroquine resistant Dd2 strain of P. falciparum.
- Kumar, Rakesh,Mohanakrishnan, Dinesh,Sharma, Abhishek,Kaushik, Naveen Kumar,Kalia, Kalpana,Sinha, Arun Kumar,Sahal, Dinkar
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experimental part
p. 5292 - 5301
(2011/02/23)
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- A new lewis acid system palladium/TMSCl for Catalytic aldol condensation of aldehydes with ketones
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Palladium on charcoal effectively catalyzed the aldol condensation reactions of different ketones with aldehydes in the presence of trimethylsilyl chloride (TMSCl). The following reactions were investigated: (1) aromatic aldehydes with cycloalkanones, (2) aromatic aldehydes with aromatic ketones, (3) cycloalkanones with aliphatic aldehydes, and (4) the self-condensation reactions of aliphatic aldehydes and cycloalkanones.
- Zhu, Yulin,Pan, Yuanjiang
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p. 668 - 669
(2007/10/03)
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- Ultrasound promoted synthesis of α,α'-bis(substituted furfurylidene) cycloalkanones and chalcones
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Condensation of furfural with cycloalkanones and substituted acetophenones catalysed by potassium hydroxide results α,α'- bis(substituted furfurylidene) cycloalkanones and chalcones in high yield under ultrasound irradiation in 4-50 min.
- Li, Ji-Tai,Chen, Guo-Feng,Wang, Jian-Xin,Li, Tong-Shuang
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p. 965 - 971
(2007/10/03)
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- Studies of Substituent Effects by Carbon-13 NMR Spectroscopy. Thiophene and Furan Chalcone Analogues
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13C NMR spectra of 39 thiophene and furan chalcone analogues in CDCl3 solutions are reported.The effect of substituents on the 13C chemical shifts in the phenyl and in the 5-membered rings is discussed. 13C NMR shifts are correlated with Hammett parameter
- Musumarra, Giuseppe,Ballistreri, Francesco P.
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p. 384 - 391
(2007/10/02)
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