- Some 1,3,5-trisubstituted pyrazoline derivatives targeting breast cancer: Design, synthesis, cytotoxic activity, EGFR inhibition and molecular docking
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Different 1,3,5-trisubstituted pyrazoline derivatives 2a-c, 3-c, 4a-f, 6a-c, 7a-f and 8a-d were prepared via condensation reaction of the appropriate chalcone 1a-c or 5a-c with various hydrazine derivatives. All compounds were screened for their cytotoxicity against breast MCF-7 cancer cell line and the normal fibroblasts WI-38. Thirteen compounds 2a, 3a, 3c, 4a-d, 6c, 7d, 7e, 8b, 8d and 8f revealed promising cytotoxicity against MCF-7 compared to the reference standard staurosporine and they were safe to the normal fibroblasts WI-38. In addition, compounds 3c, 6c, 7d, 8b and 8d elicited higher cytotoxicity than erlotinib and exhibited promising EGFR inhibitory activity at submicromolar level comparable to that of erlotinib except for compound 8b that may exert its cytotoxicity via another mechanism besides EGFR inhibition. Molecular docking of 3c, 6c, 7d, 8b and 8d in the active site of EGFR confirmed the obtained results.
- El Kerdawy, Ahmed M.,El-Ansary, Dina Y.,George, Riham F.,Kandeel, Manal
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supporting information
(2020/03/31)
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- Palladium-Catalyzed Oxidative Allylation of Sulfoxonium Ylides: Regioselective Synthesis of Conjugated Dienones
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The first examples of palladium-catalyzed allylic C-H oxidative allylation of sulfoxonium ylides to afford the corresponding conjugated dienones with moderate to good yields have been established. The features of this novel conversion include mild reaction conditions, wide substrate scope, and excellent regioselectivity.
- Li, Chunsheng,Li, Meng,Zhong, Wentao,Jin, Yangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 872 - 875
(2019/05/16)
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- Antibacterial & antitubercular activities of cinnamylideneacetophenones
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Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory
- Polaquini, Carlos R.,Torrezan, Guilherme S.,Santos, Vanessa R.,Nazaré, Ana C.,Campos, Débora L.,Almeida, Laíza A.,Silva, Isabel C.,Ferreira, Henrique,Pavan, Fernando R.,Duque, Cristiane,Regasini, Luis O.
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supporting information
(2017/11/07)
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- Highly regioselective introduction of aryl substituents via asymmetric 1,4-addition of boronic acids to linear α,β,γ,δ-unsaturated ketones
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An efficient palladium(II)-catalyzed regioselective asymmetric 1,4-conjugate addition of arylboronic acids to linear α,β,γ,δ-unsaturated ketones is developed using phosphapalladacycle catalysts. The relevant 1,4-products were obtained exclusively with per
- Gan, Kennard,Ng, Jia Sheng,Sadeer, Abdul,Pullarkat, Sumod A.
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supporting information
p. 254 - 258
(2016/01/20)
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- Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids
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In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.
- Roman, Bart I.,De Ryck, Tine,Verhasselt, Sigrid,Bracke, Marc E.,Stevens, Christian V.
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p. 1027 - 1031
(2015/02/19)
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- Synthesis, antimicrobial and cytotoxic activity of novel 1,5 benzodiazepine derivatives
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In the present study, a series of novel 2-(substituted phenyl)-3-styryl-2,3-dihydro- 1H-benzo [b] [1,4] diazepines (1-12) has been synthesized from 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones (1a-12a). 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones were prepared by condensing cinnamaldehyde with various aromatic ketones in the presence of 20% NaOH as base. Different 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones on cyclisation with o-phenylene diamine in the presence of NaOH as base resulted in 2-(substituted phenyl)-3-styryl-2,3-dihydro-1H-benzo [b] [1,4] diazepine derivatives. The structures of the newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR and mass spectroscopic studies. All titled compounds were screened for their antimicrobial and cytotoxic activities. Most of the compounds showed promising cytotoxic, antibacterial and antifungal activities.
- Bhat, K. Ishwar,Kumar, Abhishek,Prathyusha
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p. 161 - 164
(2019/01/16)
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- One-pot synthesis of cinnamylideneacetophenones and their in vitro cytotoxicity in breast cancer cells
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A series of cinnamylideneacetophenones were synthesized via a modified Claisen-Schmidt condensation reaction and evaluated for cytotoxicity against breast cancer cells using the Alamar Blue assay. Derivatives 17 and 18 bearing a 2-nitro group on the B rin
- Weldon, David J.,Saulsbury, Marilyn D.,Goh, Joshua,Rowland, Leah,Campbell, Petreena,Robinson, Laijia,Miller, Calvin,Christian, Joshua,Amis, Louisa,Taylor, Nia,Dill, Cassandra,Davis Jr., Willie,Evans, Stanley L.,Brantley, Eileen
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p. 3381 - 3384
(2014/07/22)
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- Synthesis, characterization and biological activity studies of some substituted pyrimidine derivatives
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A new series of substituted 1-phenyl-3-styryl-4,5-dihydo-1H-pyrazoles (TP1-TP9) has been synthesized by the cyclisation of chalcones with phenyl hydrazine and glacial acetic acid and substituted 4-styryl-pyrimidin-2-ols (LP1-LP9) have been synthesized by the condensation of chalcones with urea in the presence of 40% NaOH as a base. The intermediate substituted 1,5-diphenylpenta-2,4-dien-1-ones were synthesized by condensing cinnamaldehyde with various substituted aromatic ketones in presence of 20% NaOH. The title compounds obtained were characterized by IR, 1H NMR, mass spectral data and were screened for antimicrobial, anticancer and antitubercular activity.
- Ishwar Bhat,Kumar, Abhishek,Thara,Kumar, Pankaj
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p. 271 - 276
(2019/01/21)
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- Tetra-n-butylammonium bromide: A simple but efficient organocatalyst for alcohol oxidation under mild conditions
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A simple but efficient organocatalytic system with 5 mol% tetra-n-butylammonium bromide (TBAB) as the catalyst has been identified for alcohol oxidation for the first time. This organocatalytic system is compatible with a broad range of benzylic/allylic alcohols with various catalytically reactive groups. Besides, it shows excellent selectivity for secondary benzylic alcohols over aliphatic alcohols, and good selectivity over the primary benzylic alcohol site in 4-(1-hydroxyethyl)benzyl alcohol. Thus, the features of simplicity, high efficiency, selectivity and mildness of reaction conditions associated with this TBAB organocatalytic system suggest its potential for widespread use in synthetic chemistry.
- Ma, Xinyi,Li, Zhongfeng,Liu, Feijie,Cao, Shengli,Rao, Honghua
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supporting information
p. 1741 - 1746
(2014/06/09)
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- Copper-catalyzed asymmetric 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ-unsaturated ketones
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A highly regioselective and enantioselective copper-catalyzed 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ- unsaturated ketones was developed. The 1,4-addition products were obtained regioselectively in high yields with up to 98% ee. The Royal Society of Chemistry 2013.
- Ma, Zhenni,Xie, Fang,Yu, Han,Zhang, Yiren,Wu, Xiaoting,Zhang, Wanbin
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supporting information
p. 5292 - 5294
(2013/06/27)
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- Synthesis, structure, growth and characterization of an organic crystal: 1,5-diphenylpenta-2,4-dien-1-one
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1,5-Diphenylpenta-2,4-dien-1-one (DDO) chalcone single crystals, synthesized by a base-catalysed aldol condensation reaction between cinnamaldehyde and acetophenone, have been grown by the slow evaporation of an ethanol solution. The crystals belong to the orthorhombic system with centrosymmetric space group Pbca. The DDO crystals are transparent in the visible region and have a lower optical cut-off at ~445 nm with a band-gap energy of 2.87 eV. Thermogravimetry/differential scanning calorimetry thermal analysis shows that the crystal is stable up to 375 K and it has a good chemical stability. The vibrational patterns of the chalcone have been investigated by Fourier transform IR and Fourier transform Raman spectroscopy. Microhardness studies were also carried out to elucidate the mechanical behaviour. Theoretical calculations were performed using the Hartree-Fock method with 6-31G(d,p) as the basis set, and the first-order hyperpolarizability is 7.077 × 10 -30 electrostatic units, which is >25 times that of urea. The crystalline perfection evaluated by high-resolution X-ray diffraction analysis reveals multiple peaks. The molecular packing leads to a centrosymmetric arrangement, resulting in zero second harmonic generation [χ(2) = 0] efficiency. Interestingly, the bromo- and chloro-substituted chalcones are good nonlinear optical materials.
- Rajasekar,Muthu,Bhagavannarayana,Meenakshisundaram
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p. 914 - 920
(2012/10/29)
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- Tandem mass spectrometry based investigation of cinnamylideneacetophenone derivatives: Valuable tool for the differentiation of positional isomers
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Cinnamylideneacetophenones have been extensively used as versatile starting materials in numerous different transformations. The structural characterization of this type of compounds is, therefore, of crucial importance since it can give information on th
- Resende, Diana I. S. P.,Silva, Eduarda M. P.,Barros, Cristina,Domingues, M. Rosario M.,Silva, Artur M. S.,Cavaleiro, Jose A. S.
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experimental part
p. 3185 - 3195
(2012/04/10)
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- Iodine-catalysed conjugate addition of indole with α- cinnamylideneketones: Formation of β-(3-indolyl)-α,β-dihydro- α-cinnamylideneketones and bis(3-indolyl)methylbenzene
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β-(3-Indolyl)-α,β-dihydro-α-cinnamylideneketones and bis(3-indolyl)methylbenzene have been obtained in moderate to good yield by conjugate addition of indole with α-cinnamylideneketones under mild reaction condition in dry ethanol using iodine as catalyst. The structures of the products have been established from their spectral data.
- Pal, Rammohan,Mandal, Tapas K.,Mallik, Asok K.
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experimental part
p. 619 - 623
(2011/06/21)
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- Amberlyst-15 catalysed microwave assisted cross-aldol condensation between ketones and aldehydes under solvent free condition
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Amberlyst-15 has been applied as an efficient heterogeneous catalyst for the first time for rapid synthesis of α,α′-bis(arylmethylene) cycloalkanones, α,α′-bis(cinnamylidene)cycloalkanones, ′-cinnamylideneacetophenones and chalcones in very good yield by the reaction between various aldehydes and ketones under microwave irradiation. The new process for the cross-aldol condensation reaction works well in absence of any solvent. The yields are high and the process is environmentally benign.
- Pal, Rammohan,Mandal, Tapas K.,Guha, Chayan,Mallik, Asok K.
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experimental part
p. 711 - 717
(2012/03/11)
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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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- Domino multicomponent michael - Michael - Aldol reactions under phase-transfer catalysis: Diastereoselective synthesis of pentasubstituted cyclohexanes
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A simple, efficient, and environmental friendly domino multicomponent reaction to construct new cyclohexane derivatives with five new stereocenters, one of them quaternary, under phasetransfer catalysis is reported. This novel one-pot reaction allows the
- Resende, Diana I.S.P.,Oliva, Cristina G.,Silva, Artur M.S.,Almeida Paz, Filipe A.,Cavaleiro, Jose A.S.
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experimental part
p. 115 - 118
(2010/08/06)
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- Synthesis and biological activity of some 3, 5-diarylisoxazoline derivatives: Reaction of substituted chalcones with hydroxylamine hydrochloride
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A series of 3-aryl-5-styrylisoxazoline/ 3,5-diarylisoxazoline derivatives were synthesized by the reaction of appropriately substituted chalcones and hydroxylamine hydrochloride in presence of alkali in ethanol. The synthesized heterocycles have been characterized on the basis of their chemical properties and spectroscopic data. These compounds were tested for biological activity against a variety of test organisms.
- Sharma, Vandana,Sharma
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experimental part
p. 203 - 209
(2011/01/03)
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- Ultrasound-promoted synthesis of 1,5-diarylpenta-2,4-dien-1-ones catalyzed by activated barium hydroxide
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1,5-Diarylpenta-2,4-dien-1-ones were synthesized with ultrasound irradiation in the presence of activated barium hydroxide as catalyst. Compared to conventional methods, the present methodology offers several advantages such as excellent yields, simple procedure, short reaction times, and milder conditions.
- Xin, Ying,Zang, Zhi-He,Chen, Feng-Lei
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experimental part
p. 4062 - 4068
(2009/12/24)
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- Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted
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A large series of chalcones were synthesized and studied against Staphylococcus aureus and Escherichia coli. Chalcones were either unsubstituted in ring A or possessed 4′-chloro or 3′,4′,5′-trimethoxy groups. Their other ring B was variously substituted. It was found that the anti-staphylococcal activity of chalcones was related to the energy difference between the two highest occupied molecular orbitals (HOMO and HOMO-1). Presence of hydroxyl group in ring B was not a determinant factor for the anti-staphylococcal activity, but the lipophilicity of ring A of the hydroxyl chalcones was of importance.
- Batovska, Daniela,Parushev, Stoyan,Stamboliyska, Bistra,Tsvetkova, Iva,Ninova, Mariana,Najdenski, Hristo
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experimental part
p. 2211 - 2218
(2009/09/30)
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- Antifungal activity of chalcones: A mechanistic study using various yeast strains
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We reported the synthesis, antifungal evaluation and study on substituent effects of 21 chalcones. A lot of genetically defined strains belonging to different yeast genera and species, namely Saccharomyces cerevisiae, Hansenula polymorpha and Kluyveromyces lactis, were used as test organisms. Concerning the mode of the antifungal action of chalcones it was shown that DNA was probably not the main target for the chalcones. It was revealed that the yeast's intracellular glutathione and cysteine molecules play significant role as defence barrier against the chalcone action. It was also shown that chalcones may react with some proteins involved in cell separation.
- Lahtchev,Batovska,Parushev,Ubiyvovk,Sibirny
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p. 2220 - 2228
(2008/12/23)
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- Synthesis of some 3-(4-styryl-6-aryl-pyridin-2-yl)- and 3-(6-styryl-4-aryl-pyridin-2-yl) coumarins
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Various 3-(4-styryl-6-aryl-pyridin-2-yl) coumarins 4a-f and 3-(6-styryl-4-aryl-pyridin-2-yl) coumarins 5a-f have been synthesized by the reaction of 3-coumarinoyl methyl pyridinium salt I with pentadienones 2a-f and 3a-f respectectively in the presence of ammonium acetate in refluxing acetic acid.
- Brahmbhatt,Pandya, Urvish R.
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p. 145 - 149
(2007/10/03)
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- KF-Al2O3 induced the condensation of 2-nitrofluorene and para-substituted acetophenones with aromatic aldehydes
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In the presence of KF-Al2O3 as a solid base, 2-nitrofluorene 1 condensed with aromatic aldehydes 2a-f in methanol to give 2-nitrodibenzofulvenes 3a-f in high yield. The para-substituted acetophenones 4a-f reacted with cinnamic aldehyde to give 1, 5-diaryl-2, 4-pentadien-1-ones 6a-f in moderate yield.
- Yan,Sun
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p. 3809 - 3814
(2007/10/03)
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