- Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration
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The synthesis of diverse pyrazol-4-ol and isoxazole-4-ol heterocycles involving only 3 reaction steps is reported in this study. However, the synthesis of carboxamide pyrazol-4-ol has failed in the conditions used in the synthesis, acid methanol solution. The carboxamide pyrazol-4-ol decomposes via dehydration, forming the respective pyrazol. Theoretical calculations were used to elucidate the dehydration reaction. We have found a mechanism for acid-catalyzed dehydration that can explain the experimental observations. The calculated free energy profile for acid-catalyzed dehydration of the carboxamide pyrazol-4-ol and phenylpyrazole-4-ol point out that the latter is more stable in relation dehydration, with a dehydration rate 100 times smaller in acid methanol solution.
- Cipagauta Esquivel, Edna Carolina,Rufino, Virgínia Camila,Trindade Nogueira, Matheus Henrique,Carbonaro Souza, Ana Carolina,Pliego Júnior, Josefredo Rodriguez,Valle, Marcelo Siqueira
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- Synthesis, characterization and antichagasic evaluation of thiosemicarbazones prepared from chalcones and dibenzalacetones
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Chagas disease is a neglected disease, being one of the leading causes of death from infectious diseases. In view of the severity of this pathology, this work describes the synthesis of new thiosemicarbazones derived from chalcones and dibenzalacetones as potential drugs for the treatment of this disease. The structures of all compounds were elucidated by infrared (IR) and nuclear magnetic resonance (1H and 13C NMR) spectroscopies. The chalcone derived thiosemicarbazones 10-14 were tested against the intracellular amastigote form of the protozoan Trypanosoma cruzi and had their cytotoxicity assessed using LLC-MK2 cells. The compound 10 (IC50 = 12.25 μM) presented the best activity when compared with the standard drug benznidazole (IC50 = 5.64 μM).
- da Silva, Aline Alves,Maia, Pedro Ivo da Silva,Lopes, Carla Duque,de Albuquerque, Sergio,Valle, Marcelo Siqueira
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- Triarylpyrazole Derivatives as Potent Cytotoxic Agents; Synthesis and Bioactivity Evaluation Pyrazole Derivatives as Anticancer Agent
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Background During the last recent years, several anti-cancer agents were introduced for the treatment of diverse kinds of cancer. Despite their potential in the treatment of cancer, drug resistance and adverse toxicity such as peripheral neuropathy are so
- Sameem, Bilqees,Moghadam, Ebrahim Saeedian,Darabi, Majid,Shahsavari, Zahra,Amini, Mohsen
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p. 388 - 394
(2021/06/02)
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- Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions
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A ligand-free palladium-catalyzed carbonylation of vinyl iodides with arylboronic acids, permitting the synthesis of chalcones and α-branched enones, has been established. This reaction proceeds smoothly at ambient pressure and temperature, and works well even with a substoichiometric amount of base. Importantly, this mild, efficient, and operationally simple protocol is suitable for the late-stage functionalization of an epiandrosterone-derived complex molecule.
- Yang, Zhiyuan,Gong, Pei-Xue,Chen, Junjie,Zhang, Jie,Gong, Xu,Han, Wei
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supporting information
p. 1207 - 1212
(2021/06/18)
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- Methoxychalcones: Effect of methoxyl group on the antifungal, antibac-terial and antiproliferative activities
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Background: Chalcones substituted by methoxyl groups have presented a broad spec-trum of bioactivities, including antifungal, antibacterial and antiproliferative effects. However, a clear and unambiguous investigation about the relevance of this substituent on the chalcone framework has not been described. Objective: The purpose of this work is to assess the antibacterial, antifungal and antiproliferative activities of the two series of seventeen synthesized regioisomeric methoxychalcones. Series I and II were constituted by chalcones substituted by methoxyl groups on rings A (5–12) and B (13–21), respectively. In addition, the library of methoxychalcones was submitted to in silico drug-likeness and pharmacokinetics properties predictions. Methods: Methoxychalcones were synthesized and their structures were confirmed by NMR spectral data analyses. Evaluations of antimicrobial activity were performed against five species of Candida, two Gram-negative and five Gram-positive species. For antiproliferative activity, methoxychalcones were evaluated against four human tumorigenic cell lines, as well as human non-tumorigenic keratinocytes. Drug-likeness and pharmacokinetics properties were predicted using Molinspiration and PreADMET toolkits. Results: In general, chalcones of series I are the most potent antifungal, antibacterial and antipro-liferative agents. 3’, 4’, 5’-Trimethoxychalcone (12) demonstrated potent antifungal activity against Candida krusei (MIC = 3.9 μg/mL), eight times more potent than fluconazole (reference antifungal drug). 3’-Methoxychalcone (6) displayed anti-Pseudomonas activity (MIC = 7.8 μg/mL). 2’,5’-Dimethoxychalcone (9) displayed potent antiproliferative effect against C-33A (cervix), A-431 (skin) and MCF-7 (breast), with IC50 values ranging from 7.7 to 9.2 μM. Its potency was superior to curcumin (reference antiproliferative compound), which exhibited IC50 values ranging from 10.4 to 19.0 μM. Conclusion: Our studies corroborated the relevance of methoxychalcones as antifungal, antibacte-rial and antiproliferative agents. In addition, we elucidated influence of the position and number of methoxyl groups toward bioactivity. In silico predictions indicated good drug-likeness and phar-macokinetics properties to the library of methoxychalcones.
- Marques, Beatriz C.,Santos, Mariana B.,Anselmo, Daiane B.,Monteiro, Diego A.,Gomes, Eleni,Saiki, Marilia F. C.,Rahal, Paula,Rosalen, Pedro L.,Sardi, Janaina C. O.,Regasini, Luis O.
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p. 881 - 891
(2020/08/19)
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- Effect of substituents in the A and B rings of chalcones on antiparasite activity
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Chalcones are a group of natural products with many recognized biological activities, including antiparasitic activity. Although a lot of chalcones have been synthetized and assayed against parasites, the number of structural features known to be involved in this biological property is small. Thus, in the present study, 21 chalcones were synthesized to determine the effect of substituents in the A and B rings on the activity against Leishmania braziliensis, Trypanosoma cruzi, and Plasmodium falciparum. The compounds were active against L. braziliensis in a structure-dependent manner. Only one compound was very active against T. cruzi, but none of them had a significant antiplasmodial activity. The electron-donating substituents in ring B and the hydrogen bonds at C-2′ with carbonyl affect the antiparasitic activity.
- González, Luis A.,Upegui, Yulieth A.,Rivas, Luis,Echeverri, Fernando,Escobar, Gustavo,Robledo, Sara M.,Qui?ones, Wiston
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- Synthesis and theoretical study of a series of 3,5-disubstitutes pyrazoles
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In this work, we proposed the synthesis of a series of pyrazoles derivatives with different substituents on the aromatic rings. We aim to evaluate their influence on the reactivity of the compounds in reactions of α,β-unsaturated chalcones and sulfonyl hydrazide catalyzed by iodine. In order to explain their high and low yields, or the impossibility of obtaining some compounds by applied synthetic methodology, Density Functional Theory (DFT) calculations were performed. The reaction Gibbs free energy (ΔG) as well as the energy gap of the HOMO-LUMO frontier orbitals (ΔE) of some selected reactants could explain qualitatively the experimental observations in terms of synthesis yield. In this way, we believe that the chemical nature of aromatic ring substituents is relevant for the reactivity of the starting materials as well as the formation of the desired products.
- Branco, Ana Clara Alves,Couri, Mara Rubia Costa,Enes, Karine Braga,Guimar?es, Luciana,Lima, Maria Eduarda Toledo,Mateus, Marcella Fernandes Mano,Nascimento, Clebio Soares
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p. 932 - 938
(2020/12/23)
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- Development of 5-(Aryl)-3-phenyl-1H-pyrazole Derivatives as Potent Antimicrobial Compounds
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A series of 16 chalcone compounds were synthesized by Claisen-Schmidt condensation of various aldehydes with acetophenone using KOH as a base in ethanol. The reaction affords the desired products in good yields. Then all the 16 compounds were converted into pyrazoles by treating with hydrazine hydrate in ethanol under reflux condition. Both chalcones and pyrazoles were screened for their in vitro antibacterial (Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa) and antifungal (Aspergillus flavus, Chrysosporium keratinophilum and Candida albicans) activity. Biological activities of these compounds were compared with those of commercially available antibiotic ampicillin and antifungal agent miconazole. Pyrazoles were found to be most active and effective than corresponding chalcones for antimicrobial activity. Out of the 7 pyrazole compounds tested for antibacterial and antifungal activity, 5 compounds, 4h, 4j, 4l, 4m and 4n are turned out to be potent antimicrobial agents. Therefore these derivatives could serve as a highly promising molecules for further development.
- Nagendra Chowdary,Umashankara,Dinesh,Girish,Ramesha Baba
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- Discovery of novel chalcone-dithiocarbamates as ROS-mediated apoptosis inducers by inhibiting catalase
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Novel chalcone-dithiocarbamate hybrids were designed, synthesized and evaluated for antiproliferative activity against selected cancer cell lines (MGC803, MCF7, and PC3). Among these analogues, (E)-2-oxo-2-((4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)am
- Fu, Dong-Jun,Li, Jia-Huan,Yang, Jia-Jia,Li, Ping,Zhang, Yan-Bing,Liu, Simeng,Li, Zhong-Rui,Zhang, Sai-Yang
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p. 375 - 385
(2019/02/15)
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- A class of novel tubulin polymerization inhibitors exert effective anti-tumor activity via mitotic catastrophe
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In current work, a class of novel 4,5-dihydro-1H-pyrazole-1-carboxylate derivatives (E01-E28) were designed, synthesized and evaluated. Among them, the most potent compound E24 exhibited comparable activity against a panel of cancer cells (GI50
- Zhang, Ya-Liang,Li, Bo-Yan,Yang, Rong,Xia, Lin-Ying,Fan, A-Li,Chu, Yi-Chun,Wang, Lin-Jian,Wang, Zhong-Chang,Jiang, Ai-Qin,Zhu, Hai-Liang
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p. 896 - 910
(2019/01/04)
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- A benzenesulfonyl pyrazoline derivatives such preparation and application of (by machine translation)
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The invention discloses a novel tubulin inhibitors benzenesulfonyl pyrazoline derivatives preparation method and in anti-tumor applications. Formula (I) has a structure shown in: Wherein: R1 Selected from: - H, - F, - Cl, - CH3 , - CF3 , - OCH3 , - OH, - NO2 ; R2 Selected from: - H, - Cl, - F, - I, - CH3 , - CH2 CH3 , - (CH2 )2 CH3 , - CH (CH3 )2 , - OH, - NO2 . (by machine translation)
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Paragraph 0018-0021
(2019/05/28)
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- Structure-activity relationship studies and in vitro and in vivo anticancer activity of novel 3-aroyl-1,4-diarylpyrroles against solid tumors and hematological malignancies
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Novel 3-aroyl-1,4-diarylpyrrole derivatives were synthesized to explore structure-activity relationships at the phenyls at positions 1 and 4 of the pyrrole. The presence of amino phenyl rings at positions 1 and 4 of the pyrrole ring were found to be a crucial requirement for potent antitumor activity. Several compounds strongly inhibited tubulin assembly through binding to the colchicine site. Compounds 42, 44, 48, 62 and 69 showed antitumor activity with low nanomolar IC50 values in several cancer cell lines. Compound 48 was generally more effective as an inhibitor of glioblastoma, colorectal and urinary bladder cancer cell lines; 69 consistently inhibited CML cell lines and demonstrated superiority in nilotinib and imatinib resistant LAMA84-R and KBM5-T315I cells. In animal models, compound 48 exhibited significant inhibition of the growth of T24 bladder carcinoma and ES-2 ovarian clear cell carcinoma tumors. Compounds 48 and 69 represent robust lead compounds for the design of new broad-spectrum anticancer agents active in different types of solid and hematological tumors.
- Bai, Ruoli,Biagioni, Stefano,Cavallini, Chiara,Coluccia, Addolorata Maria Luce,Coluccia, Antonio,Da Pozzo, Eleonora,Hamel, Ernest,La Regina, Giuseppe,Liu, Te,Martini, Claudia,Mazzoccoli, Carmela,Mazzoni, Cristina,Nalli, Marianna,Orlando, Viviana,Puxeddu, Michela,Shen, Hongliang,Silvestri, Romano
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- Regioselective hydrodehalogenation of aromatic α-and β-halo carbonyl compounds by cui in isopropanol
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An operationally efficient and regioselective hydrodehalogenation methodology of aromatic α-and β-halo carbonyl compounds has been developed using CuI in isopropanol at 90 °C under basic condition. The catalytic system effectively dehalogenates chloride, bromide, and iodide groups and af-forded high yield (up to 97 %) as carbonyl compounds. The methodology is environmentally friendly and demonstrates excellent tolerance to a broad range of electronically rich and poor substituents.
- Parveen, Iram,Khan, Danish,Ahmed, Naseem
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p. 759 - 764
(2019/01/09)
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- Synthesis and biological evaluation of pyrimidine bridged combretastatin derivatives as potential anticancer agents and mechanistic studies
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A number of pyrimidine bridged combretastatin derivatives were designed, synthesized and evaluated for anticancer activities against breast cancer (MCF-7) and lung cancer (A549) cell lines using MTT assays. Most of the synthesized compounds displayed good
- Kumar, Bhupinder,Sharma, Praveen,Gupta, Vivek Prakash,Khullar, Madhu,Singh, Sandeep,Dogra, Nilambra,Kumar, Vinod
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p. 130 - 140
(2018/03/23)
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- Microtubule polymerization inhibitor containing pyrazoline structure and application thereof
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The invention relates to the field of medicine and specifically relates to application of a microtubule polymerization inhibitor (which is shown in a formula I) containing a pyrazoline structure in preparing drugs for treating and resisting tumor.
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Paragraph 0058; 0059
(2019/01/08)
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- Synthesis and evaluation of modified chalcone based p53 stabilizing agents
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Tumor suppressor protein p53 induces cell cycle arrest and apoptotic cell death in response to various cellular stresses thereby preventing cancer development. Activation and stabilization of p53 through small organic molecules is, therefore, an attractive approach for the treatment of cancers retaining wild-type p53. In this context, a series of nineteen chalcones with various substitution patterns of functional groups including chloro, fluoro, methoxy, nitro, benzyloxy, 4-methyl benzyloxy was prepared using Claisen-Schmidt condensation. The compounds were characterized using NMR, HRMS, IR and melting points. Evaluation of synthesized compounds against human colorectal (HCT116) and breast (CAL-51) cancer cell lines revealed potent antiproliferative activities. Nine compounds displayed GI50 values in the low micromolar to submicromolar range; for example (E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (SSE14108) showed GI50 of 0.473 ± 0.043 μM against HCT116 cells. Further analysis of these compounds revealed that (E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (SSE14105) and (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (SSE14106) caused rapid (4 and 8-h post-treatment) accumulation of p53 in HCT116 cells similar to its induction by positive control, Nutlin-3. Such activities were absent in 3-(4-methoxyphenyl)propiophenone (SSE14106H2) demonstrating the importance of conjugated ketone for antiproliferative and p53 stabilizing activity of the chalcones. We further evaluated p53 levels in the presence of cycloheximide (CHX) and the results showed that the p53 stabilization was regulated at post-translational level through blockage of its degradation. These chalcones can, therefore, act as fragment leads for further structure optimization to obtain more potent p53 stabilizing agents with enhanced anti-proliferative activities.
- Iftikhar, Sunniya,Khan, Sardraz,Bilal, Aishah,Manzoor, Safia,Abdullah, Muhammad,Emwas, Abdel-Hamid,Sioud, Salim,Gao, Xin,Chotana, Ghayoor Abbas,Faisal, Amir,Saleem, Rahman Shah Zaib
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supporting information
p. 4101 - 4106
(2017/08/22)
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- Novel polyfunctional pyridines as anticancer and antioxidant agents. Synthesis, biological evaluation and in silico ADME-T Study
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Two series of novel alkoxylated 2-oxo(imino)-3-pyridinecarbonitriles (structurally-relevant to some reported anticancer pyridines with phosphodiesterase 3A (PDE3A) inhibitory activity) were synthesized and evaluated for their in vitro differential tumor c
- Badr, Mona Hany,Rostom, Sherif Ahmed Fawzi,Radwan, Mohammed Fouad
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p. 442 - 454
(2017/05/17)
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- Synthesis and cytotoxic activities of some pyrazoline derivatives bearing phenyl pyridazine core as new apoptosis inducers
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The cyclization of chalcones 3a-3u with 3-hydrazinyl-6-phenylpyridazine 7 under basic condition led to the formation of new pyrazoline derivatives 8a-8u. All final compounds were characterized by spectral and elemental analyses. They were screened for their antiproliferative activities against A549 (lung), HepG-2 (liver), CaCo-2 (intestinal) and MCF-7 (breast) cancer cell lines. Some of the synthesized compounds exhibited promising antiproliferative activities especially compound 8k with IC50values of 8.33, 1.67 and 10?μM against HepG-2, MCF-7 and CaCo-2 cancer cell lines, respectively. Moreover, their antiproliferative activity was due to apoptosis rather than necrosis induction except compound 8h which exhibited equal apoptotic and necrotic properties. Compound 8k showed 5 fold increase in caspase-3 activity indicating that the apoptosis proceeds via caspase-3 activation.
- George, Riham F.,Fouad, Marwa A.,Gomaa, Iman E.O.
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- Kinetic Resolution of β-Sulfonyl Ketones through Enantioselective β-Elimination using a Cation-Binding Polyether Catalyst
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Reported herein is the first enantioselective β-elimination reaction catalyzed by a chiral cation-binding polyether. By using this catalytic protocol, a wide range of β-sulfonyl ketones could be effectively resolved with high stereoselectivity (S up to >300). Key to the success of this process is the favorable secondary interactions of the catalyst with the Lewis basic groups on the sulfone substrate. The enone product of this process can be easily converted into the racemic starting material, and allows an effective recycling and overall synthesis of chiral β-sulfonyl ketones in high yield and excellent enantioselectivity.
- Li, Liang,Liu, Yidong,Peng, Yang,Yu, Lei,Wu, Xiaoyan,Yan, Hailong
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supporting information
p. 331 - 335
(2016/01/25)
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- New pyrrole derivatives with potent tubulin polymerization inhibiting activity as anticancer agents including hedgehog-dependent cancer
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We synthesized 3-aroyl-1-arylpyrrole (ARAP) derivatives as potential anticancer agents having different substituents at the pendant 1-phenyl ring. Both the 1-phenyl ring and 3-(3,4,5-trimethoxyphenyl)carbonyl moieties were mandatory to achieve potent inhi
- La Regina, Giuseppe,Bai, Ruoli,Coluccia, Antonio,Famiglini, Valeria,Pelliccia, Sveva,Passacantilli, Sara,Mazzoccoli, Carmela,Ruggieri, Vitalba,Sisinni, Lorenza,Bolognesi, Alessio,Rensen, Whilelmina Maria,Miele, Andrea,Nalli, Marianna,Alfonsi, Romina,Di Marcotullio, Lucia,Gulino, Alberto,Brancale, Andrea,Novellino, Ettore,Dondio, Giulio,Vultaggio, Stefania,Varasi, Mario,Mercurio, Ciro,Hamel, Ernest,Lavia, Patrizia,Silvestri, Romano
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p. 6531 - 6552
(2014/10/16)
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- An efficient simple one-pot synthesis, characterization and structural studies of some 1,2,3,5-tetraarylpentane-1,5-diones
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A series of 1,2,3,5-tetraarylpentane-1,5-diones (9-23) were synthesised by simple one-pot method and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral techniques. The structure of 3-(4-fluorophenyl)-1,2,5-triphenylpentane-1,5-dione (10) was determined by single crystal X-ray diffraction analysis. The compound 10 crystallize in monoclinic crystal system, in C2/c space group. The torsional angle between the two keto groups was found to be -29.50. The C(23)C(22)C(15)C(8)C(7) chain is almost planar with "W" conformation and observed maximum deviation is 0.122 ? for C(15) from the C(23)/C(22)/C(15)/C(8)/C(7) plane.
- Senthilkumar,Neelakandan,Manikandan
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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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- One-pot synthesis of multifunctionalized cyclopropanes
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A facile one-step synthetic protocol toward multifunctionalized cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a [2C+1C] annulation.
- Chang, Meng-Yang,Chen, Yi-Chia,Chan, Chieh-Kai
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p. 2257 - 2263
(2014/03/21)
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- Synthesis of quinolines from N-tosyl-1-azadienes
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A route to aryl-substituted quinolines from N-tosyl 1-azadienes is described. The key steps are a [4 + 2] cycloaddition with benzyne followed by base treatment of the 1,4-dihydroquinoline product. The N-tosyl 1-azadienes were prepared from readily accessible cinnamaldehyde and chalcone substrates by condensation with p-TsNH2. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Stokes, Sean,Mead, Keith T.
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supporting information
p. 2627 - 2633
(2013/07/26)
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- Microwave synthesis, characterization and bio-efficacy evaluation of novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives
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Novel chalcone based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol derivatives were synthesized and characterized by using spectral techniques like IR, 1H NMR, 13C NMR, COSY, DEPT, and GC-MS. All these compounds were screened for anti-fungal, anti-bacterial and anti-oxidant activity. Cyclohexenone derivatives, in general, showed better anti-fungal and anti-bacterial activity than parent chalcones. Whereas, all the Indazole derivatives showed very good anti-oxidant activity and some were also found to be active as anti-bacterial agent. Among the screened compounds, 15 was found to be most active as anti-fungal agent (against Rhizoctonia solani, LC 50 = 2.36 μg mL-1), 15b was found to be most active anti-bacterial agent (against Klebsiella pneumonia, MIC = 24.68 μg mL -1) and 14b emerged as most active anti-oxidant (IC50 = 19.81 μg mL-1).
- Shakil,Singh, Manish K.,Sathiyendiran,Kumar,Padaria, Jasdeep C.
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p. 120 - 131
(2013/03/14)
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- Design, synthesis and molecular docking study of some substituted 4,5-dihydro-2H-indazole derivatives as potential anti-inflammatory agents
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A new series of 4,5-dihydro-2H-indazoles was synthesized and evaluated for anti-inflammatory activity using formalin-induced paw edema and turpentine oil-induced granuloma pouch bioassays. In addition, the inhibitory activity of cyclooxygenase, ulcerogenic effect, and acute toxicity (ALD50) values were also determined. Compounds 10, 13, 15, 16, 18 and 22 were proved to display distinctive anti-inflammatory profiles with a fast onset of action. They revealed super GI safety profile and are well tolerated by the experimental animals with high safety margin (ALD50 > 300 mg/Kg). The same active compounds exhibited moderate to powerful selectivity profile towards the inhibition of COX-2 enzyme. Docking poses for the most active compounds separately in the active site of human COX-2 enzyme were also obtained.
- Badr, Mona H.,Elbayaa, Rasha Y.,El-Ashmawy, Ibrahim M.
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p. 718 - 730
(2013/09/23)
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- One-pot synthesis of multifunctionalized m-terphenyls
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A facile one-step synthetic protocol toward multifunctionalized m-terphenyls 5 and sulfonyl m-terphenyls 6 is developed from substituted chalcones 1 and allyl sulfone 2 in good yields via a [3C+3C] annulation. The NaH-mediated annulation features transition metal catalyst-free condition. Chalcones 1 with the functional groups tolerance are easily prepared via Claisen-Schmidt condensation of substituted benzaldehydes 3 with acetophenone 4 in a qualitative yield under an aqueous alkaline methanolic solution.
- Chang, Meng-Yang,Chan, Chieh-Kai,Lin, Shin-Ying,Wu, Ming-Hao
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p. 9616 - 9624
(2013/10/22)
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- Synthesis, spectroscopic characterization, in vitro cytotoxic and structure activity relationships of some mononuclear Ru(II) complexes
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New mononuclear Ru(II) complexes [Ru(A)2(B)}2+, where A= 2,2'-bipyridine/1,10-phenanthroline and B= 3,4,5-tri-OCH3-DPC, 4-CH3-DPC, 4-N(CH3)2-DPC, 4-NO2-DPC, N-BITSZ, PTSZ and PINH, were prepared and characterized by spectroscopic methods. The in vitro cytotoxic activities of the complexes and their corresponding ligands were investigated against the human cancer TlyMPhocyte cell lines molt 4/c8 and CEM and the murine tumor leukemia cell line L1210, human promyelocytic leukemia cells (HL-60) and Bel-7402 liver cancer cells by MTT assay. The complexes [Ru(A)2(B)}2+ (A= 1,10-phenanthroline, B= 3,4,5-tri-OCH3-DPC) exerts rather more potent activities against all of these cell lines, especially for CEM and L1210. Ru complexes and structure-activity relationships and anticancer mechanisms are also discussed.
- Thota, Sreekanth,Vallala, Srujana,Imran, Mohammad,Mekala, Sravani,Anchuri, Shyam Sunder,Karki, Subhas Somalingappa,Yerra, Rajeshwar,Balzarini, Jan,De Clercq, Erik
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p. 1031 - 1045
(2013/07/28)
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- Synthesis and Evaluation of a Series of 3,4,5-Trimethoxycinnamic Acid Derivatives as Potential Antinarcotic Agents
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A series of 3,4,5-trimethoxycinnamic acid derivatives was prepared and evaluated for antinarcotic effects on morphine dependence in mice and binding affinities on serotonergic receptors. The key synthetic strategies involve generation of ketones 6-7, esters 9-12 through condensation reaction, and amides 13-19 via coupling reaction using 1-hydroxybenzotriazole/ethyl(dimethylaminopropryl)carbodiimide system in high yield. We found that the naloxone-induced morphine withdrawal syndrome was significantly suppressed by new synthetic 3,4,5-trimethoxycinnamic acid derivatives (20mg/kg/day). Most of 3,4,5-trimethoxycinnamic acid derivatives were found to have high affinity to 5-HT1A receptor. The naloxone-induced morphine withdrawal syndrome was attenuated by (+)8-OH-DPAT (0.1mg/kg/day, i.p.), a 5-HT1A receptor agonist. In cortical neuronal cells, (+)8-OH-DPAT (1μm) produced an elevation of the pERK 1/2 expression, and the elevated pERK levels were inhibited by WAY 100635, a 5-HT1A receptor-specific antagonist. Interestingly, the pERK levels were increased by the 3,4,5-trimethoxycinnamic acid derivatives and the derivatives-mediated changes in pERK levels were blocked by the WAY 100635. These results suggested that new synthetic 3,4,5-trimethoxycinnamic acid derivatives have a potential antinarcotic effect through acting as a 5-HT1A receptor agonist in mice.
- Jung, Jae-Chul,Moon, Sohyeon,Min, Dongguk,Park, Woo Kyu,Jung, Mankil,Oh, Seikwan
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p. 389 - 398
(2013/04/10)
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- Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
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Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C6-C 3-C6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Springer Science+Business Media, LLC 2011.
- Nepali, Kunal,Kadian, Kanika,Ojha, Ritu,Dhiman, Rajni,Garg, Atul,Singh, Gagandip,Buddhiraja, Abhishek,Bedi, Preet Mohinder Singh,Dhar, Kanaya Lal
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p. 2990 - 2997
(2012/10/29)
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- Biotransformation of chalcones by the endophytic fungus aspergillus flavus isolated from paspalum maritimum trin
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The fungus Aspergillus flavus isolated as endophytic of the plant Paspalum maritimum Trin. was evaluated for its potential application in biotransformation reactions. The compounds chalcone (1), 3,4,5-trimethoxychalcone (2) and 2,3,4,4′-tetramethoxychalco
- Corre?a, Marivaldo J. C.,Nunes, Fa?tima M.,Bitencourt, Heriberto R.,Borges, Fa?bio C.,Guilhon, Giselle M.S.P.,Arruda, Mara S.P.,Marinho, Andrey M.R.,Santos, Alberdan S.,Alves, Cla?udio N.,Brasil, Davi S.B.,Santos, Lourivaldo S.
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experimental part
p. 1333 - 1338
(2012/04/23)
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- Synthesis, antioxidant evaluation, and quantitative structure-activity relationship studies of chalcones
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Synthesis, antioxidant activity, and quantitative structure-activity relationship (QSAR) of 25 of chalcone derivatives is reported here. They were synthesized by Claisen-Schmidt reaction and were characterized by FTIR, NMR, and mass spectroscopy. Antioxidant activity is evaluated through four different methods namely, superoxide radical-scavenging, hydrogen peroxide scavenging, reducing power, and DPPH radical-scavenging assays. Generally, compounds with -SCH3 and -OCH3 in the para position of the A-ring and -OH in the B-ring were more active than others. In few cases some of the compounds were more active than ascorbic acid or butylated hydroxytoluene. QSAR was developed correlating the antioxidant activity with the structural features of the compounds and the predictive capability of the models was estimated using internal and external validation methods. All the predictions were within the 99% confidence level. Spatial, structural, and lipophilic properties of the compounds determine their antioxidant properties.
- Sivakumar,Prabhakar,Doble
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scheme or table
p. 482 - 492
(2012/04/04)
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- Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents
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Chalcones have been identified as interesting compounds with cytotoxicity, anti-inflammatory and antioxidant properties. In the present study, simple methoxychalcones were synthesized by Claisen-Schmidt condensation reaction and evaluated for above biological activities. The structures of the compounds were established by IR, 1H NMR and mass spectral analysis. The data revealed that compound 3s (99-100% at 10 μM concentration) completely inhibit the selected five human cancer cell lines as compared to standard flavopiridol and gemcitabine (70-90% at 700 nM and 500 nM concentrations, respectively), followed by 3a, 3n, 3o, 3p, 3q, 3r. Among the tested compounds 3l, 3m, 3r, and 3s exhibited promising anti-inflammatory activity against TNF-α and IL-6 with 90-100% inhibition at 10 μM concentration. DPPH free radical scavenging activity was given by the compounds 3o, 3n, 3l, 3r, 3m, 3a, 3p, 3c and 3s at 1 mM concentration. Overall, 3s was obtained as lead compound with promising anticancer, anti-inflammatory and antioxidant activities. Bioavailability of compounds were checked by in vitro cytotoxicity study and confirmed to be nontoxic. The structure activity relationship (SAR) and in silico drug relevant properties (HBDs, HBAs, PSA, c Log P, ionization potential, molecular weight, EHOMO and ELUMO) further confirmed that the compounds were potential candidates for future drug discovery study.
- Bandgar, Babasaheb P.,Gawande, Shrikant S.,Bodade, Ragini G.,Totre, Jalinder V.,Khobragade, Chandrahas N.
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experimental part
p. 1364 - 1370
(2010/04/26)
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- Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
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The α-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G2/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 μM; CA4, 0.10 μM) and compete with [3H]colchicine for binding to tubulin (8% [3H]colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity.
- Ducki, Sylvie,Rennison, David,Woo, Meiko,Kendall, Alexander,Chabert, Jeremie Fournier Dit,McGown, Alan T.,Lawrence, Nicholas J.
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supporting information; experimental part
p. 7698 - 7710
(2010/03/24)
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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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- Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives
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In order to develop relatively small molecules as antimycobacterial agents, twenty-five chalcones were synthesized, their activity was evaluated, and quantitative structure-activity relationship (QSAR) was developed. The synthesis was based on the Claisen
- Sivakumar,Seenivasan, S. Prabu,Kumar, Vanaja,Doble, Mukesh
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p. 1695 - 1700
(2007/10/03)
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- Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of 3,5-dimethyl pyrazoles, 3-methyl pyrazol-5-ones and 3,5-disubstituted pyrazolines
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3,5-Dimethyl pyrazole 3a-d and 3-methyl pyrazol-5-one 4a-d derivatives of diclofenac, ibuprofen, flurbiprofen and 2,4-dichlorophenoxy acetic acid have been synthesized. In addition, substituted pyrazoline derivatives of ibuprofen 6a-e have also been prepared by treating different chalcones 5a-e with ibuprofen hydrazide. Some of the newly synthesized compounds are screened for anti-inflammatory activity and few compounds showing 80% activity are selected for analgesic, ulcerogenic and lipid peroxidation activities.
- Amir, Mohd,Kumar, Shikha
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p. 2532 - 2537
(2007/10/03)
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- Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents
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A series of substituted chalcones and their corresponding pyrazoles were synthesized and evaluated for in vitro cytotoxic activity against a panel of human cancer cell lines. Out of 93 compounds screened, 8 compounds, 1s, 3i,j,n, 4i,j,n and 4s, showed marked activity. Compounds 4j,n and 4s were found to be the most promising in this study. SAR is also discussed.
- Bhat,Dhar,Puri,Saxena,Shanmugavel,Qazi
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p. 3177 - 3180
(2007/10/03)
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- Carbonic anhydrase inhibitors. Part 36*. Inhibition of isozymes I and II with Schiff bases derived from chalkones and aromatic/heterocyclic sulfonamides
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A series of 27 Schiff bases was prepared by reaction of chalkones with sulfanilamide and 5-amino-1,3,4-thiadiazole-2-sulfonamide. The new compounds were characterized by analysis and standard physico-chemical methods. They possess good inhibitory properties towards isozymes I and II of carbonic anhydrase. Structure-activity effects in this series of inhibitors are also discussed.
- Supuran,Popescu,Ilisiu,Costandache,Banciu
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p. 439 - 447
(2007/10/03)
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- Chalcones: A new class of antimitotic agents
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A series of chalcones was evaluated as antimitotic agents. One of these, (E)-1-(2,5-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]-2-methyl-2-propen- 1-one) (73), was found to be an effective antimitotic agent at a concentration of 4 nM in an in vitro HeLa
- Edwards,Stemerick,Sunkara
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p. 1948 - 1954
(2007/10/02)
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- Studies on Cycloimmonium Ylids: Synthesis of Some New 2,4,6-Triarylsubstituted Pyridines via Pyridinium Ylids
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2,4,6-Triarylsubstituted pyridines (4a-r) have been synthesised by the reaction of pyridinium ylids (1a-c) with α,β-unsaturated ketones (2a-f) in the presence of ammonium acetate and acetic acid.These compounds (4a-r) have been characterised on the basis
- Singhal, R. K.,Mishra, Naresh K.
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p. 1079 - 1080
(2007/10/02)
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