- Studies of solvation of ketocyanine dyes in homogeneous and heterogeneous media by UV/Vis spectroscopic method
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Solvation characteristics of ketocyanine dyes (I-VI) have been investigated in pure solvents and heterogeneous media by absorption and fluorescence studies. The dyes are good reporters of solvent polarity. In protic solvents they exist as equilibrium mixt
- Das,Pramanik,Banerjee,Bagchi
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- Synthesis and inhibitory activity of dimethylamino-chalcone derivatives on the induction of nitric oxide synthase
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A series of nine dimethylamino-chalcone derivatives (1,3-diaryl-propenones) was synthesized and screened as potential inhibitors of NO and PGE2 production in the RAW 264.7 macrophage cell line. 4-Dimethylamino-2′,5′-dimethoxychalcone (6) was fo
- Rojas, Javier,Domínguez, José N,Charris, Jaime E,Lobo, Gricela,Payá, Miguel,Ferrándiz, M.Luisa
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- Synthesis, Crystal Structure, and Photophysical Properties of 4-(4-(Dimethylamino)phenyl)-6-phenylpyrimidin-2-amine
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The pyrimidine core is present in a wide variety of compounds that show interesting fluorescent properties and have been used as pigments and dyes. In this research, we synthesized 4-(4-(dimethylamino)phenyl)-6-phenylpyrimidin-2-amine (compound 9) from ch
- Aguilar, Luis F.,Bravo, Manuel A.,Fuentealba, Mauricio,Mellado, Marco,Sánchez-González, Rodrigo,Sariego-Kluge, Rafaela,Valdés-Navarro, Franco
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- Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2″-hydroxy naphthalen-1″-yl)-1,5-diphenyl-2-pyrazolines
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Five new 1,3,5-triphenyl-2-pyrazolines were synthesised by reacting 1,3-diphenyl-2-propene-1-one with phenyl hydrazine hydrochloride and another five new 3-(2″-hydroxy naphthalen-1″-yl)-1,5-diphenyl-2-pyrazolines were synthesised by reacting 1-(2′-hydroxy
- Rajendra Prasad,Lakshmana Rao,Prasoona,Murali,Ravi Kumar
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- Anchoring pyrazolines on a 2,2′:6′,2″-terpyridine backbone
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Introducing pyrazoline derivatives into the classical 2,2′:6′,2″-terpyridine (2,2′:6′,2″-tpy) backbone leads to the synthesis of a new class of compounds, 4′-pyrazolinyl-2,2′:6′,2″-tpys. Six such derivatives bearing differently substituted pyrazolines hav
- Liu,Li, Li,Xiong, Hangxing,Chan, Corinna,Cheng, Jessica,Zhang, Guoqi
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- Synthesis and biological activity of 4-aryl-3-benzoyl-5- phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives as novel potent inhibitors of advanced glycation end product
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Diabetic complications and their detrimental effects caused by sugar derived substances, have been the serious issue for the last few years and have yet not been fully combated. The key point of the present study is to synthesize some newer chemical entities which can eradicate such ailments to the maximum possible extent. So with this aim synthesis of some biologically interesting spiro-indolone-pyrrolidine derivatives was accomplished by 1,3-dipolar cycloaddition reaction of azomethine ylide 6 generated in situ from isatin and benzyl amine with the substituted α,β-unsaturated carbonyl compounds 3 as dipolarophile, leading to the formation of new 4-aryl-3-benzoyl-5- phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives 7 stereoselectively in excellent yields. The synthesized compounds have been screened for their advanced glycation end (AGE) product formation inhibitory activity on the basis of their ability to inhibit the formation of AGEs in the bovine serum albumin (BSA)-glucose assay and have been found to exhibit significant activity against AGE formation.
- Kaur, Anjandeep,Singh, Baldev,Vyas, Bhawna,Silakari, Om
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- Nonlinear optical studies and structure-activity relationship of chalcone derivatives with in silico insights
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Nine chalcones were prepared via Claisen-Schmidt condensation, and characterized by UV–vis, IR1H NMR13C NMR and mass spectrometry. One of the representative member 4-NDM-TC has been studied via single crystal XRD and the TGA/DTA tech
- Kar, Swayamsiddha,Adithya,Shankar, Pruthvik,Jagadeesh Babu,Srivastava, Sailesh,Nageswara Rao
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- Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative Structure–Activity Relationship Models
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Chalcones are a group of molecules with a broad spectrum of biological activities, being especially appealing for their antiproliferative effects on several cancer cell lines. For this reason, we synthesized 23 chalcones with good to excellent yields and assessed their effect on the viability of the SH-SY5Y neuroblastoma cell line and on primary human fibroblasts. The results indicated that 18 of these compounds were more active than 5-fluorouracil in the cancer cell line and one of them was more selective than this reference drug. To identify structural features related to the antiproliferative activity of these compounds, as well as, the selectivity on the cancer cell line, a 2D-QSAR analysis was performed. The QSAR model (q2 = 0.803; r2 = 0.836) showed that lipophilicity (CLogP) is the most important factor to increase their cytotoxicity on the cancer cell line. On the other hand, the selectivity QSAR model (q2 = 0.917; r2 = 0.916) showed that changes in the Mulliken’s charge of the carbonyl group and at the C4’ position in the chalcone core can increase the selectivity for SH-SY5Y cell line compared to normal fibroblasts.
- Mellado, Marco,Madrid, Alejandro,Reyna, Mauricio,Weinstein-Oppenheimer, Caroline,Mella, Jaime,Salas, Cristian O.,Sánchez, Elizabeth,Cuellar, Mauricio
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- α-Trifluoromethyl Chalcones as Potent Anticancer Agents for Androgen Receptor-Independent Prostate Cancer
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α-Trifluoromethyl chalcones were prepared and evaluated for their antiproliferative activities against androgen-independent prostate cancer cell lines as well as five additional types of human tumor cell lines. The most potent chalcone 5 showed superior antitumor activity in vivo with both oral and intraperitoneal administration at 3 mg/kg. Cell-based mechanism of action studies demonstrated that 5 induced cell accumulation at sub-G1 and G2/M phases without interfering with microtubule polymerization. Furthermore, several cancer cell growth-related proteins were identified by using chalcone 5 as a bait for the affinity purification of binding proteins.
- Goto, Masuo,Izumi, Kouji,Mizokami, Atsushi,Naito, Renato,Nakagawa-Goto, Kyoko,Saito, Yohei
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- Effect of Donor-Acceptor Coupling on TICT Dynamics in the Excited States of Two Dimethylamine Substituted Chalcones
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Significant effect of coupling between the electron donor and acceptor groups in intramolecular charge transfer (ICT) dynamics has been demonstrated by comparing the photophysical properties of two isomeric N,N-dimethylaminochalcone derivatives (namely, DMAC-A and DMAC-B). In the case of the DMAC-B molecule, the distance between the donor (N,N-dimethylaniline or DMA) and the acceptor (carbonyl) groups is larger by one ethylene unit as compared to that in the case of DMAC-A. The excited singlet (S1) states of both the isomers have strong ICT character but their photophysical properties are remarkably different. In polar solvents, fluorescence quantum yields (and the lifetimes of the S1 state) of DMAC-A are more than 2 orders of magnitude lower (and shorter) than those of DMAC-B. Remarkable differences in the photophysical properties of these two isomers arise due to occurrence of the ultrafast twisting of the DMA group (or the TICT process) during the course of deactivation of the S1 state of the DMAC-A molecule, but not in the case of DMAC-B. In the later case, because of the presence of a large energy barrier along the twisting coordinate(s), TICT is not a feasible process, and hence, the S1 state of DMAC-B has the planar ICT structure. In the DMAC-A molecule, the strength of coupling between the donor and acceptor groups is relatively stronger because of a shorter distance between these groups. Femtosecond transient absorption spectroscopic measurements and DFT/TDDFT calculations have been adopted to establish the above aspects of the relaxation dynamics of the S1 states of these two isomeric chalcones.
- Ghosh, Rajib,Palit, Dipak K.
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- Palladium-catalyzed decarboxylative arylation of benzoylacrylic acids toward the synthesis of chalcones
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It has been found that readily available 3-benzoylacrylic acids undergo palladium-catalyzed decarboxylative arylation with arylboronic acids in the presence of a copper salt oxidant to produce chalcone derivatives. The decarboxylative arylation could also be achieved using aryl halides as the alternative aryl source to expand the applicable scope.
- Unoh, Yuto,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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- 1,3,5-Triarylpyrazolines - PH-driven off-on-off molecular logic devices based on a "receptor1-fluorophore-spacer-receptor2" format with internal charge transfer (ICT) and photoinduced electron transfer (PET) mechanisms
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The excited state photophysical properties of the 1,3,5-triarylpyrazolines 1-4 were studied in methanol and 1:1 (ν/ν) methanol-water, as well as 1:4 (ν/ν) methanol-water and water by fluorescence spectroscopy. The molecules 2-4 incorporate a "receptorsub
- Zammit, Ramon,Pappova, Maria,Zammit, Esther,Gabarretta, John,Magri, David C.
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- Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation
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The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.
- Nicholson, Kieran,Langer, Thomas,Thomas, Stephen P.
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supporting information
p. 2498 - 2504
(2021/04/13)
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- Inhibition of Caco-2 and MCF-7 cancer cells using chalcones: synthesis, biological evaluation and computational study
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Cancer is the second death cause worldwide, with breast and colon cancer among the most prevalent types. Traditional treatment strategies have several side effects that inspire the development of novel anticancer agents derived from natural sources, like chalcone derivatives. For this investigation, twenty-three chalcones (4a-w) were synthesized and evaluated as antiproliferative agents against MCF-7 and Caco-2 cells, finding three and two compounds with similar or higher antiproliferative activity than daunorubicin, while only two chalcones showed better selectivity indexes than daunorubicin on MCF-7. From these results, we developed good-performance QSAR models (r > 0.850, q2>0.650), finding several structural features that could modify chalcone activity and selectivity. According to these models, chalcones 4w and 4t have high potency and selectivity against Caco-2 and MCF-7, respectively, which make them attractive candidates for hit-to-lead development of ROS-independent pro apoptotic agents.
- Aguilar, Luis F.,Coddou, Claudio,Jara-Gutierrez, Carlos,Mellado, Marco,Reyna-Jeldes, Mauricio,Villena, Joan,Weinstein-Oppenheimer, Caroline
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supporting information
(2021/10/02)
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- Synthesis, characterization and biological evaluation of new 3,5-disubstituted-pyrazoline derivatives as potential anti-Mycobacterium tuberculosis H37Ra compounds
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A total of fourteen pyrazoline derivatives were synthesized through cyclo-condensation reactions by chalcone derivatives with different types of semicarbazide. These compounds were characterized by IR, 1D-NMR (1H, 13C and Distortionless Enhancement by Polarization Transfer-DEPT-135) and 2D-NMR (COSY, HSQC and HMBC) as well as mass spectroscopy analysis (HRMS). The synthesized compounds were tested for their antituberculosis activity against Mycobacterium tuberculosis H37Ra in vitro. Based on this activity, compound 4a showed the most potent inhibitory activity, with a minimum inhibitory concentration (MIC) value of 17 μM. In addition, six other synthesized compounds, 5a and 5c–5g, exhibited moderate activity, with MIC ranges between 60 μM to 140 μM. Compound 4a showed good bactericidal activity with a minimum bactericidal concentration (MBC) value of 34 μM against Mycobacterium tuberculosis H37Ra. Molecular docking studies for compound 4a on alpha-sterol demethylase was done to understand and explore ligand– receptor interactions, and to hypothesize potential refinements for the compound.
- Azmi, Mohamad Nurul,Che Omar, Mohammad Tasyriq,Osman, Hasnah,Parumasivam, Thaigarajan,Supratman, Unang,Wong, Kok Tong
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- Fluorescent Molecular Logic Gates Driven by Temperature and by Protons in Solution and on Solid
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Temperature-driven fluorescent NOT logic is demonstrated by exploiting predissociation in a 1,3,5-trisubstituted Δ2-pyrazoline on its own and when grafted onto silica microparticles. Related Δ2-pyrazolines become proton-driven YES an
- West, Matthew E. S.,Yao, Chao-Yi,Melaugh, Gavin,Kawamoto, Kyoko,Uchiyama, Seiichi,de Silva, A. Prasanna
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supporting information
p. 13268 - 13274
(2021/08/06)
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- Cascade Reaction of α, β-Unsaturated Ketones and 2-Aminoaryl Alcohols for the Synthesis of 3-Acylquinolines by a Copper Nanocatalyst
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3-Acylquinolines possess widespread applications in functional chemicals. However, the convenient and selective synthesis of such important substructures has to date remained a challenge. Herein, we report a method to access 3-acylquinolines from α, β-unsaturated ketones and 2-aminoaryl alcohols in one pot with a copper nanocatalyst supported on nitrogen-silica-doped carbon (Cu/N?SiO2?C). Mechanistically, the construction of the product involves a cascade procedure including radical-type oxidation of 2-aminoaryl alcohols, aza-Michael addition and annulation. This developed protocol proceeds with merits of mild reaction conditions, good functional group tolerance, earth-abundant and reusable copper catalyst, easily available stocks and O2 as the sole oxidant, which provides an alternative way for the sustainable synthesis of quinoline derivatives. (Figure presented.).
- Liu, Yuan,Wang, Chen,Tong, Yixin,Ling, Yong,Zhou, Changjian,Xiong, Biao
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supporting information
p. 4422 - 4429
(2021/08/07)
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- Zinc-coordinated aza-pyrrolidone optical diagnosis and treatment reagent with long-wave absorption characteristic as well as preparation and application thereof
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The invention discloses a zinc-coordinated aza-pyrrolidone optical diagnosis and treatment reagent with a long-wave absorption characteristic as well as preparation and application thereof. The optical diagnosis and treatment reagent is composed of a metal center and an aza-pyrrolidone auxiliary ligand; the whole preparation process is simple, the prepared complex has a long absorption wavelength, and the absorption wavelength can be prolonged along with the change of the aza-pyrrolidone auxiliary ligand, so that the optical diagnosis and treatment reagent has a deep tissue penetration depth in the field of living body application; the complex can be excited by near-infrared light and can emit near-infrared light, so that the damage of an excitation light source to a biological sample can be weakened; and the complex can be used in the field of photodynamic and photothermal combined therapy guided by biological imaging, and has an important application prospect.
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Paragraph 0065-0069
(2021/06/23)
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- Silver-coordinated aza-pyrrolidone complex, and preparation method and application thereof
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The invention discloses a silver-coordinated aza-pyrrolidone complex, and a preparation method and application thereof. The complex is composed of an aza-pyrrolidone ligand, a silver metal center and a triphenylphosphine auxiliary ligand, the raw materials are relatively cheap, and the synthesis method is simple; and the prepared complex shows relatively strong absorption in an ultraviolet region and a near-infrared region, and can be excited by near-infrared light, so that the damage of an excitation light source to a biological sample can be weakened, and the complex has relatively deep tissue penetration depth in the field of living body application, and is more suitable for biological imaging and deep photodynamic photo-thermal combined treatment.
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Paragraph 0036-0039
(2021/07/08)
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- Pyrazoline analogs as potential anticancer agents and their apoptosis, molecular docking, MD simulation, DNA binding and antioxidant studies
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N-formyl pyrazoline derivatives (3a–3l) were designed and synthesized via Michael addition reaction through cyclization of chalcones with hydrazine hydrate in presence of formic acid. The structural elucidation of N-formyl pyrazoline derivatives was carri
- Rana, Manish,Arif, Rizwan,Khan, Faez Iqbal,Maurya, Vikas,Singh, Raja,Faizan, Md Imam,Yasmeen, Shama,Dar, Sajad Hussain,Alam, Raquib,Sahu, Ankita,Ahmad, Tanveer,Rahisuddin
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- Corrosion Inhibition of Mild Steel by newly Synthesized Pyrazole Carboxamide Derivatives in HCl Acid Medium: Experimental and Theoretical Studies
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Corrosion inhibition of mild steel in hydrochloride acid solution was performed by a two pyrazole carboxamides named 5-(4-(dimethylamino)phenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide DPC-1 and (E)-5-(4-(dimethylamino)phenyl)-3-(4-(dimethylamino)s
- Benali, O.,Boudjellal, F.,F., Boudjellal,Ferhat, M.,Guendouzi, A.,Ouici, H. B.,Sehmi, A.
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- 1,2,4-Triphenylpyrroles: Synthesis, Structure and Luminescence Properties
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Pyrroles are widely found in natural products and play an important role in biological processes. Certain pyrrole derivatives are fluorescent and may be used as molecular probes or biomarkers in the diagnosis of diseases, such as Alzheimer's or Parkinson'
- Ferreira, Joana R. M.,Guieu, Samuel,Nunes Da Silva, Raquel,Rocha, Jo?o,Silva, Artur M. S.
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supporting information
p. 632 - 634
(2020/03/27)
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- Synthesis, molecular docking and α-glucosidase inhibitory activity study of 2,4,6-triaryl pyrimidine derivatives
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Background: α-Glucosidase inhibitors hinder the carbohydrate digestion and play an important role in the treatment of diabetes mellitus. α-glucosidase inhibitors available on the market are acarbose, miglitol, and voglibose. However, the use of acarbose is diminishing due to related side effects like diarrhea, bloating and abdominal distension. Objectives: This study aimed to synthesize 2,4,6-triaryl pyrimidines derivatives, screen their α-glucosidase inhibitory activity, perform kinetic and molecular docking studies. Methods: A series of 2,4,6-triaryl pyrimidine derivatives were synthesized and their α-glucosidase inhibitory activity was screened in vitro. Pyrimidine derivatives 4a-m were synthesized via a two-step reaction with a yield between 49 and 93%. The structure of the synthesized compounds was confirmed by different spectroscopic techniques (IR, NMR and MS). The in vitro α-glucosidase inhibition activities of the synthesized compounds 4a-m was also evaluated against Saccharomyces cerevisiae α-glucosidase. Results and Discussion: The majority of synthesized compounds had α-glucosidase inhibitory activity. Particularly compounds 4b and 4g were the most active compounds with an IC50 value of 125.2± 7.2 and 139.8 ± 8.1 μM respectively. The kinetic study performed for the most active compound 4b revealed that the compound was a competitive inhibitor of Saccharomyces cerevisiae α-glucosidase with Ki of 122 μM. The molecular docking study also revealed that the two compounds have important binding interactions with the enzyme active site. Conclusion: 2,4,6-triarylpyrimidine derivative 4a-m were synthesized and screened for α-glucosidase inhibitory activity. Most of the synthesized compounds possess α-glucosidase inhibitory activity, and compound 4b demonstrated the most significant inhibitory action as compared to acarbose.
- Abdollahi, Mohammad,Amini, Mohsen,Bule, Mohammed Hussen,Esfandyari, Roghaieh,Faramarzi, Mohammad Ali,Tafesse, Tadesse Bekele
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p. 1216 - 1226
(2020/10/06)
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- Synthesis and evaluation of chalcone and its derivatives as potential anticholinergic agents
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Background: Structural similarity in Chalcone and Pyrazoline brought our intention for the analysis of such compounds. This study involved the synthesis of chalcones and their pyrazoline derivatives and their screening as cholinesterase inhibitors. The newly synthesized compounds were also investigated for their antioxidant potential. Methods: Chalcones were synthesized by well-established methods of synthesis and their structural elucidation was carried out by H-NMR, 13C-NMR, Mass spectrometry and FTIR. For the determination of inhibition potency of synthesized compounds, spectrophotometric method was applied whereas, DPPH free radical scavenging method was used to check the antioxidant ability. Results: Chalcones and their pyrazoline derivatives were synthesized and characterised by 1HNMR, 13C-NMR, Mass spectrometry and FTIR. The compounds were screened for their anti-Alzheimer activity, which exhibited that compounds 1g, 1c and 1h, 1g showed strong inhibitory potency against acetylcholinesterase and butyrylcholinesterase, respectively. DPPH radical scavenging method was applied to check anti-oxidant potential of synthesized compounds and results explored that among all the synthesized compounds only compounds 1c and 1b showed strong scavenging potential. Conclusion: Chalcone and their pyrazoline derivatives were synthesized and screened for their anti-Alzheimer and antioxidant potential. The experimental results of anti-Alzheimer activity were compared with molecular docking studies, which showed that compounds 1g, 1c and 1h, 1g were active against AChE and BChE, respectively. Among the synthesized compounds 1c and 1b were found to be most potent antioxidants. These results suggest that compound 1b, 1c, 1g and 1h may further be explored for further developments.
- Murtaza, Shahzad,Mir, Khoula Zubair,Tatheer, Adina,Ullah, Raja Summe
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p. 322 - 332
(2019/06/20)
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- Dual evaluation of some novel chalcone annulated pyrazolines as anti-inflammatory and antimicrobial agents via in-silico target study on cyclooxygenase-2
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A novel series of chalcone bearing pyrazoline moieties were (P1 to P7) synthesized and characterized by various analytical techniques. The anti-inflammatory studies showed the compounds P1, P2, P5, and P6 have produced the noteworthy inhibition on protein
- Prabha, Thangavelu,Jubie, Selvaraj,Selvamani, Palanisamy,Latha, Subbiah,Sivakumar, Thangavel
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p. 3159 - 3169
(2019/11/11)
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- Preparation method of chalcone, dihydrochlcone and flavone compound and application
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The invention discloses a preparation method of chalcone, dihydrochlcone and flavone compound and an application. The preparation method and application disclosed by the invention have the beneficialeffects that 3,4',6'-trihydroxy-4-methoxychalcone has stronger inhibiting effect to a-glucosidase and can be used for reducing postprandial hyperglycemia; 4-dimethylaminochalcone, 4-hydroxychalcone, 3-hydroxy-4-methoxychalcone and 3,4',6'-trihydroxy-4-methoxychalcone have more obvious inhibiting effect to nonenzymatic glycation and can be used for treating diabetes and atherosclerosis.
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Paragraph 0017
(2019/01/08)
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- Straightforward synthesis of quinolines from enones and 2-aminobenzyl alcohols using an iridium-catalyzed transfer hydrogenative strategy
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A new protocol for the direct synthesis of quinolines from enones and 2-aminobenzyl alcohols via iridium-catalyzed transfer hydrogenative reactions has been demonstrated. This method employs easily available [IrCp?Cl2]2/t-BuOK as the efficient catalyst system, proceeding with the merits of high step- and atom efficiency, mild reaction conditions and operational simplicity. The experimental studies suggest that the reactions start with transfer hydrogenation, followed by the Friedl?nder reaction to give the final products.
- Xiong, Biao,Wang, Yingying,Liu, Yuan,Bao, Yandan,Liu, Zhaoguo,Zhang, Yanan,Ling, Yong
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supporting information
p. 5707 - 5711
(2018/08/17)
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- Transition-Metal-Free Highly Chemoselective and Stereoselective Reduction with Se/DMF/H2O System
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A novel metal-free reduction system, in which H2Se (or HSe-) produced in situ from Se/DMF/H2O acts as the active reducing species, has been developed. By using water as an inexpensive, safe, and environmentally friendly surrogate as the hydrogen donor, this new reduction system incorporating Se/DMF/H2O displayed high selectivity and good activity in the reduction of α,β-unsaturated ketones and alkynes. Therefore, this reduction system has great potential to be a general and practical reduction methodology in organic transformation.
- Li, Hong-Chen,An, Cui,Wu, Ge,Li, Guo-Xing,Huang, Xiao-Bo,Gao, Wen-Xia,Ding, Jin-Chang,Zhou, Yun-Bing,Liu, Miao-Chang,Wu, Hua-Yue
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supporting information
p. 5573 - 5577
(2018/09/12)
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- Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles
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N-Methyl- and N-alkylamines represent important fine and bulk chemicals that are extensively used in both academic research and industrial production. Notably, these structural motifs are found in a large number of life-science molecules and play vital roles in regulating their activities. Therefore, the development of convenient and cost-effective methods for the synthesis and functionalization of amines by using earth-abundant metal-based catalysts is of scientific interest. In this regard, herein we report an expedient reductive amination process for the selective synthesis of N-methylated and N-alkylated amines by using nitrogen-doped, graphene-activated nanoscale Co3O4-based catalysts. Starting from inexpensive and easily accessible nitroarenes or amines and aqueous formaldehyde or aldehydes in the presence of formic acid, this cost-efficient reductive amination protocol allows the synthesis of various N-methyl- and N-alkylamines, amino acid derivatives, and existing drug molecules.
- Senthamarai, Thirusangumurugan,Murugesan, Kathiravan,Natte, Kishore,Kalevaru, Narayana V.,Neumann, Helfried,Kamer, Paul C. J.,Jagadeesh, Rajenahally V.
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p. 1235 - 1240
(2018/02/09)
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- Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models
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A series of new pyrimidine–triazine hybrids (4a–t) was designed and synthesized, from which potent anticonvulsant agents were identified. Most of the compounds exhibited promising anticonvulsant activity against the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) tests, along with minimal motor impairment with higher safety compared to the standard drugs, phenytoin and carbamazepine. In the series, 5-(4-(4-fluorophenyl)-6-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4o) and 5-(6-(4-hydroxy-3-methoxyphenyl)-4-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4s) emerged as most potent anticonvulsant agents with median doses of 22.54 and 29.40 mg/kg (MES ED50), 285.02 and 293.42 mg/kg (scPTZ ED50), and 389.11 and 412.16 mg/kg (TD50), respectively. Docking studies were also performed for all synthesized compounds to get insight into the binding pattern toward the GABAA receptor as a possible mechanism of their anticonvulsant action, and in silico ADME studies were carried out to predict the safety and stability of the molecules. The increased GABA level in the experimental animals in the neurochemical estimation assay confirmed their GABAergic modulating activity. The most potent compounds were also evaluated for their neurotoxic and hepatotoxic effects. Fortunately, they did not show any sign of neurotoxicity or hepatotoxicity, suggesting that they have a broad spectrum of anticonvulsant activity with a large safety margin. Together, this research suggested that 4o and 4s may serve as leads in the discovery and development of new anticonvulsant drugs.
- Sahu, Meeta,Siddiqui, Nadeem,Naim, Mohd. Javed,Alam, Ozair,Yar, Mohammad Shahar,Sharma, Vidushi,Wakode, Sharad
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- An eco-friendly synthesis of 2-pyrazoline derivatives catalysed by CeCl 3· 7 H 2O
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Abstract: 1,3,5-triaryl-2-pyrazoline derivatives were synthesised by a condensation reaction between chalcones and phenyl hydrazine using cerium chloride heptahydrate as a catalyst. All these reactions were carried out in ethyl lactate (70%) as a green solvent. Easy and efficient work up, recyclability of solvent and catalyst are the key merits of this protocol. Graphical Abstract:: SYNOPSIS A facile protocol for the synthesis of 1,3,5-triaryl-2-pyrazolines is described. The solvent ethyl lactate, obtained from renewable sources, is biodegradable. The catalyst CeCl 3· 7 H 2O is a water-tolerant Lewis acid with low toxicity. Easy and clean work up, recyclable solvent and catalyst are merits of the protocol. The reaction works well for all systems giving good yields of the desired products.[Figure not available: see fulltext.].
- Bhat, Prabhat,Shridhar, Gomathi,Ladage, Savita,Ravishankar, Lakshmy
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p. 1441 - 1448
(2017/09/25)
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- Rational design, synthesis and in vitro evaluation of allylidene hydrazinecarboximidamide derivatives as BACE-1 inhibitors
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BACE-1 (β-secretase) is considered to be one of the promising targets for treatment of Alzheimer's disease as it catalyzes the rate limiting step of Aβ-42 production. Herein, we report a novel class of allylidene hydrazinecarboximidamide derivatives as moderately potent BACE-1 inhibitors, having aminoguanidine substitution on allyl linker with two aromatic groups on either side. A library of derivatives was designed based on the docking studies, synthesized and evaluated for BACE-1 inhibition in vitro. The designed ligands displayed interactions with the catalytic aspartate dyad through guanidinium functionality. Further, the aromatic rings placed on either side of the linker occupied S1 and S3 active site regions contributing to the activity. These ligands were also predicted to follow Lipinski rule and cross blood brain barrier. Compound 2.21, having high docking score, was found to be most active with IC50 of 6.423 μM indicating good correlation with docking prediction.
- Jain, Priti,Wadhwa, Pankaj K.,Rohilla, Shilpa,Jadhav, Hemant R.
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supporting information
p. 33 - 37
(2015/12/18)
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- Characterization of the Fluorescence Properties of 4-Dialkylaminochalcones and Investigation of the Cytotoxic Mechanism of Chalcones
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Understanding the mechanisms responsible for the various biological activities of chalcones, particularly the direct cellular targets, presents an unmet challenge. Here, we prepared a series of fluorescent chalcone derivatives as chemical probes for their
- Zhou, Bo,Jiang, Peixin,Lu, Junxuan,Xing, Chengguo
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p. 539 - 552
(2016/08/26)
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- Synthesis, biological evaluation, quantitative-SAR and docking studies of novel chalcone derivatives as antibacterial and antioxidant agents
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In the present study, a series of chalcone derivatives including 17 new compounds were synthesised; their antibacterial activities against eleven bacteria, and their free radical-scavenging activities using DPPH were evaluated. All compounds showed significant antibacterial activities against both Grampositive and Gram-negative bacteria. In particular, compound IIIf strongly inhibited Staphylococcus aureus (JMC 2151) and Enterococcus faecalis (CARS 2011-012) with MIC values of 6.25 μg mL-1 and 12.5 μg mL-1, respectively, which are comparable to that of the standard antibiotic, nalidixic acid. Compound IIIg also inhibited S. aureus with a MIC value similar to that of nalidixic acid (6.25 μg mL-1). Furthermore, like nalidixic acid (MIC value of 25 μg mL-1), compounds IIIa, IIIc and IIId inhibited Listeria monocytogenes (ATCC 43256) with MIC values of 25 μg mL-1, 12.5 μg mL-1 and 25 μg mL-1, respectively. Quantitative structure-activity relationship (Q-SAR) studies using physicochemical calculations indicated that the antibacterial activities of chalcone derivatives correlated well with predicted physicochemical parameters (logP and PSA). Docking simulation by positioning the most active compound IIIf in the active site of the penicillin-binding protein (PBP-1b) of S. aureus was performed to explore the feasible binding mode. Furthermore, most of the compounds synthesised exhibited significant DPPH radical-scavenging activity, although compounds IIc and IIIc exhibited the greatest antioxidant activity with IC50 values of 1.68 μM and 1.44 μM, respectively, comparable to that of the standard antioxidant, ascorbic acid (1.03 μM).
- Alam, Mohammad Sayed,Rahman, S. M. Mostafizur,Lee, Dong-Ung
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p. 1118 - 1129
(2015/06/08)
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- Application of bis(oxazoline) in asymmetric β-amination of chalcones
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An effective enantioselective β-amination of chalcones with N-bromosuccinimide into β-imidoketones using a bis(oxazoline) ligand is described. A wide variety of β-imidoketone derivatives containing various functional groups can be obtained with high enantioselectivities. The products are highly valuable molecules regarding their vast applications as building blocks of drugs and biologically active compounds.
- Deng, Tao,Wang, Hongjun,Cai, Chun
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supporting information
p. 102 - 105
(2015/02/19)
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- Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach
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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.
- Ventura, Thatiana Lopes Biá,Calixto, Sanderson Dias,De Azevedo Abrahim-Vieira, Bárbara,De Souza, Alessandra Mendon?a Teles,Mello, Marcos Vinícius Palmeira,Rodrigues, Carlos Rangel,De Mariz E Miranda, Leandro Soter,De Souza, Rodrigo Octavio Mendon?a Alves,Leal, Ivana Correa Ramos,Lasunskaia, Elena B.,Muzitano, Michelle Fraz?o
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p. 8072 - 8093
(2015/05/20)
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- Synthesis of some pyrazolone derivatives and evaluation of its antibacterial and cytotoxic activity
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A series of novel pyrazolone derivative were synthesized by two different schemes (scheme-1 by the reaction of phenyl hydrazine and ethyl acetoacetate with substituted benzaldehydes PYR-1 to PYR-4) and (by the reaction of synthesized chalcone with phenyl hydrazine PYR-5) and characterised with its physical parameters (M.P, colour, %yield, solubility etc.). The entire synthesized compound was tested for their antimicrobial activity against Grampositive and Gram-negative strains of bacteria and brimeshrimp bioassay was conducted for evaluation of cytotoxic activity The Investigation of antimicrobial screening data revealed that most of the tested compounds showed moderate to good antimicrobial activity. And cytotoxicity activity of compounds was also found to be satisfactory.
- Parajuli, Rishiram,Banerjee, Janmajoy,Khanal, Hemanta
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p. 2099 - 2106
(2016/02/27)
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- A novel transition metal-free conjugate reduction of α,β-unsaturated ketones with tosylhydrazine as a hydrogen source
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A novel and efficient method has been developed for the chemoselective conjugate reduction of α,β-unsaturated ketones with tosylhydrazine as a hydrogen source to the corresponding saturated ketones in moderate to good yields. The present protocol does not require the use of transition metal, and is efficient being applicable to a wide range of substrates (25 examples).
- Zhou, Xiaomeng,Li, Xiaokang,Zhang, Wei,Chen, Junmin
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supporting information
p. 5137 - 5140
(2015/02/19)
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- Novel and green approach for the nanocrystalline magnesium oxide synthesis and its catalytic performance in Claisen-Schmidt condensation
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Magnesium oxide is one of the most promising solid base material having catalytic applications. A novel, simple, efficient, inexpensive, additives free and green synthesis protocol for magnesium oxide nano-particles using concentrated solar energy has been reported. Using magnesium acetate and 1, 4-butanediol magnesium oxide nanoparticles in the range of 5-20 nm was prepared. The driving force for the nanoparticles synthesis was obtained by using concentrated solar energy as a dual energy source in the form of radiational and thermal effect. The resulting magnesium oxide nanoparticles are found to be excellent and reusable catalyst for the Claisen-Schmidt condensation under solvent free condition.
- Patil, Aniruddha B.,Bhanage, Bhalchandra M.
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- Two expedient 'one-pot' methods for synthesis of β-aryl-β- mercaptoketones over anhydrous potassium carbonate or amberlyst-15 catalyst
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Two expedient one-pot methods have been developed for synthesis of β-aryl-β-mercaptoketones using acetophenones, benzaldehydes and thiols as starting materials. The methods involve microwave irradiation (5min) of 1:1 mixtures of acetophenones and benzaldehydes over neutral alumina supported anhydrous potassium carbonate or amberlyst-15 in the first step, and that is followed by addition of thiol to the resulting material and keeping at room temperature for 1.5 h. Indian Academy of Sciences.
- Guha, Chayan,Mondal, Rina,Pal, Rammohan,Mallik, Asok K.
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p. 1463 - 1470
(2014/04/03)
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- Lithium hydroxide mediated synthesis of 3,4-disubstituted pyrroles
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LiOH·H2O in ethanol was found to be an effective reagent for the synthesis of 3,4-disubstituted pyrrole derivatives by the van Leusen method. In situ formation of chalcones from aromatic aldehydes and enolisable ketones, and their subsequent reaction with tosylmethyl isocyanide resulted in the formation and precipitation of pyrrole derivatives from the reaction medium, in good yields. The solvation effect of the polar medium facilitates the reaction. The Royal Society of Chemistry 2013.
- Sharma, Ratnesh,Kumar, Kapil,Chouhan, Mangilal,Grover, Vikas,Nair, Vipin A.
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p. 14521 - 14527
(2013/09/02)
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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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- Spectral properties of chalcone containing triphenylamino structural unit in solution and in polymer matrices
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Novel chalcones (3-phenyl-1-phenylprop-2-en-1-ones) substituted on one end (position 3) with electron donating diphenylaminophenyl substituent and on the other end (position 1) with thiophenes with variable electronic effects (CH-1-CH-5) were prepared. Th
- Danko, Martin,Andics, Anita,Kosa, Csaba,Hrdlovic, Pavol,Vegh, Daniel
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experimental part
p. 1257 - 1265
(2012/03/27)
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- Synthesis of chalcones with anticancer activities
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Several chalcones were synthesized and their in vitro cytotoxicity against various human cell lines, including human breast adenocarcinoma cell line MCF-7, human lung adenocarcinoma cell line A549, human prostate cancer cell line PC3, human adenocarcinoma cell line HT-29 (colorectal cancer) and human normal liver cell line WRL-68 was evaluated. Most of the compounds being active cytotoxic agents, four of them with minimal IC50 values were chosen and studied in detail with MCF-7 cells. The compounds 1, 5, 23, and 25 were capable in eliciting apoptosis in MCF-7 cells as shown by multiparameter cytotoxicity assay and caspase-3/7, -8, and -9 activities (p 0.05). The ROS level showed 1.3-fold increase (p 0.05) at the low concentrations used and thus it was concluded that the compounds increased the ROS level eventually leading to apoptosis in MCF-7 cells through intrinsic as well as extrinsic pathways.
- Syam, Suvitha,Abdelwahab, Siddig Ibrahim,Al-Mamary, Mohammed Ali,Mohan, Syam
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experimental part
p. 6179 - 6195
(2012/09/07)
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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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- Evaluation and discovery of novel synthetic chalcone derivatives as anti-inflammatory agents
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Major anti-inflammatory agents, steroids and cyclooxygenase, were proved to have serious side effects. Here, a series of chalcone derivatives were synthesized and screened for anti-inflammatory activities. QSAR study revealed that the presence of electron-withdrawing groups in B-ring and electron-donating groups in A-ring of chalcones was important for inhibition of LPS-induced IL-6 expression. Further, compounds 22, 23, 26, 40, and 47 inhibited TNF-α and IL-6 release in a dose-dependent manner and decreased LPS-induced TNF-α, IL-1β, IL-6, IL-12, and COX-2 mRNA production. Mechanistically, compounds 23 and 26 interfered with JNK/NF-κB signaling and dose-dependently prevented ERK and p38 activation. In addition, 23 and 26 exhibited a significant protection against LPS-induced death and were able to block high glucose-activated cytokine profiles in macrophages. Together, these data show a series of anti-inflammatory chalcones with potential therapeutic effects in inflammatory diseases.
- Wu, Jianzhang,Li, Jianling,Cai, Yuepiao,Pan, Yong,Ye, Faqing,Zhang, Yali,Zhao, Yunjie,Yang, Shulin,Li, Xiaokun,Liang, Guang
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experimental part
p. 8110 - 8123
(2012/01/07)
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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 of Aza-BODIPY boron difluoride PDT agents to promote apoptosis in HeLa cells
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BF2 Chelated azadipyrromethene dyes fluoresce in the near infrared and have potential applications in photodynamic therapy. When irradiated above 600nm these aza-BODIPY compounds react with triplet O 2 in the body to form a reactive
- Priefer, Ronny,Griffithsa, Justin R.,Ludwiga, Janelle N.,Skelhorne-Grossb, Graham,Greene, Robert S.
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experimental part
p. 368 - 373
(2012/05/07)
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- Highly activated Michael acceptor by an intramolecular hydrogen bond as a fluorescence turn-on probe for cyanide
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An activated Michael acceptor type of probe by an intramolecular hydrogen bond has shown a selective fluorescence turn-on response to cyanide through a conjugated addition of the nucleophilic anion to the enone probe with a 1300-fold increase in its fluor
- Park, Seokan,Kim, Hae-Jo
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supporting information; experimental part
p. 9197 - 9199
(2011/02/22)
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- Iodine-catalyzed efficient synthesis of chalcones by grinding under solvent-free conditions
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Chalcones are useful intermediates in organic synthesis and exhibit a large number of different biological activities. Chalcones have been synthesized in high yields by Claisen-Schmidt condensation of substituted acetophenones with various aromatic aldehydes in the presence of 10 mol% of iodine at room temperature by grinding under solvent-free conditions.
- Wang, Hongshe,Zeng, June
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experimental part
p. 1209 - 1212
(2009/12/03)
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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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- A substituted BF2-chelated tetraarylazadipyrromethene as an intrinsic dual chemosensor in the 650-850 nm spectral range
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The synthesis and spectral analysis of a new class of long wavelength intrinsic fluorosensor is reported. Chemosensor performance reveals large off/on fluorescence intensity responses to acid analyte with low response to microenvironment polarity. Applica
- Killoran, John,McDonnell, Shane O.,Gallagher, John F.,O'Shea, Donal F.
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p. 483 - 489
(2008/09/17)
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- Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans
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A large series of chalcones were synthesized and studied for activity against Candida albicans. The SAR analysis showed that the antifungal activity was highly dependent on the substitution pattern of the aryl rings and correlated to a large extent with the ability of compounds to interact with sulfhydryl groups. The most active were the hydroxylated chalcones as their activity related to the location of the phenolic group in the aryl ring B as follows: o-OH > p-OH ~ 3,4-di-OH > m-OH. These and other correlations obtained strongly contribute to the knowledge for design of anticandidal chalcones.
- Batovska,Parushev,Slavova,Bankova,Tsvetkova,Ninova,Najdenski
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