- Chalcones and bis-chalcones analogs as DPPH and ABTS radical scavengers
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Background: A number of synthetic scaffolds, along with natural products, have been identified as potent antioxidants. The present study deals with the evaluation of varyingly substituted, medicinally distinct class of compounds “chalcones and bis-chalcon
- Bale, Adebayo Tajudeen,Salar, Uzma,Khan, Khalid Mohammed,Chigurupati, Sridevi,Fasina, Tolulope,Ali, Farman,Ali, Muhammad,Sekhar Nanda, Sitansu,Taha, Muhammad,Perveen, Shahnaz
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p. 249 - 257
(2021/04/21)
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- Environmentally benign synthesis of substituted pyrazoles as potent antioxidant agents, characterization and docking studies
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Oxidative stress is an important cause of neurogenerative diseases; treatment with a reliable antioxidant with no side effects is a potential tool?to overcome with such diseases. The aim of this study is to explore new and effective antioxidants and their
- Vagish, Channa Basappa,Dileep Kumar, Achutha,Kumara, Karthik,Vivek, Hamse Kameshwar,Renuka, Nagamallu,Lokanath, Neratur Krishnappagowda,Ajay Kumar, Kariyappa
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p. 479 - 493
(2020/09/01)
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- Convenient Synthesis of Novel Chalcone and Pyrazoline Sulfonamide Derivatives as Potential Antibacterial Agents
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Abstract: Novel chalcone sulfonamide derivatives were synthesized starting from benzophenones and aldehydes in 3 steps. Also, (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one was converted to different pyrazoline in four steps. The synthesis of s
- Bonakdar,Sadeghi,Aghaei,Beheshtimaal,Nazifi,Massah
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p. 371 - 381
(2020/06/30)
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- Isoxazoles-a biocompatible radical scavenging agents: Citrus juice mediated environmentally benign synthesis and characterization
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This study demonstrates the efficient eco-friendly synthesis of a series of isoxazole derivatives 5a-h through (3+2) annulation of chalcones 3a-h and hydroxylamine (4) in citrus juice medium. The synthesized compounds were characterized by spectroscopic a
- Raghavendra,Prabhudeva,Dileep Kumar,Ajay Kumar,Jayadevappa
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p. 2997 - 3001
(2021/01/06)
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- Chalcones and bis-chalcones: As potential α-amylase inhibitors; synthesis, in vitro screening, and molecular modelling studies
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Despite of a diverse range of biological activities associated with chalcones and bis-chalcones, they are still neglected by the medicinal chemist for their possible α-amylase inhibitory activity. So, the current study is based on the evaluation of this c
- Tajudeen Bale, Adebayo,Mohammed Khan, Khalid,Salar, Uzma,Chigurupati, Sridevi,Fasina, Tolulope,Ali, Farman,Kanwal,Wadood, Abdul,Taha, Muhammad,Sekhar Nanda, Sitanshu,Ghufran, Mehreen,Perveen, Shahnaz
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p. 179 - 189
(2018/05/24)
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- An improved, efficient and microwave assisted synthetic method for the synthesis of chalcone oximes: An experimental and computational study
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Chalcone oximes are important molecules in organic chemistry. Extant literature contains several methods for conversion of chalcones to their oxime forms but rapid and efficient new methods need to be developed. In this study; we have investigated a new, microwave assisted synthetic method for conversion of chalcones to their oxime forms. For this purpose, a series of known chalcones were synthesized and converted to their oxime forms employing the method being examined. The results show that the proposed method is efficient, providing time and energy savings. In the second part of our study, DFT calculations with B3LYP method have been performed on the synthesized molecules and computational results have been compared with the experimentally obtained data. All DFT calculations were performed at the B3LYP/6-31G(d), B3LYP/6-311G(d, p) and B3LYP/6-311+G(2d, p) levels of theory. NMR calculations were carried out using GIAO and CSGT methods. Additionally, MEP maps, FMOs, some global reactivity descriptors and Mulliken atomic charges for the synthesized compounds were computationally determined with the same basis sets.
- Erdogan, Taner,Erdogan, Fatma Oguz
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- Synthesis and antifungal activity of chalcone derivatives
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In the present study, using chalcone as a lead compound, a series of its derivatives (compounds 1-30) were designed and synthesised. Their activity of anti-pathogenic fungi of plants has been evaluated. It is found that these compounds have good antifunga
- Zheng, Yuanyuan,Wang, Xuesong,Gao, Sumei,Ma, Min,Ren, Guiming,Liu, Huabing,Chen, Xiaohong
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p. 1804 - 1810
(2015/03/04)
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- Efficient Protocol for the Synthesis of Novel Spiro[acenaphthylene-1,2′-pyrrolidin]-2-one Compounds
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An efficient catalyst-free synthesis of 3′-benzoyl-4′,5′-diphenyl-2H-spiro[acenaphthylene-1,2′-pyrrolidin]-2-one derivatives via one-pot 1,3-dipolar cycloaddition of acenaphthenequinone, arylmethyl amines, and chalcones with high regioselectivity is described. The structure of the cycloadducts were characterized by infrared, high-resolution mass spectrometry (electrospray ionization), 1H NMR, and 13C NMR spectra, and the structure of 4a was confirmed using x-ray single-crystal structure analysis.
- Lin, Yan,Fu, Zhijie,Shen, Tianhua,Che, Fengfeng,Song, Qingbao
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supporting information
p. 2188 - 2194
(2015/09/22)
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- Oxygen as single oxidant for two steps: Base-free one-pot Pd(ii)-catalyzed alcohol oxidation & arylation to halogen-intact β-aryl α,β-enones
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Using oxygen as the sole oxidant for two steps, we developed a new method to synthesize β-aryl α,β-enones by fine-tuning the Pd(ii)-catalyzed oxidation of allyl alcohol to subsequent arylation with arylboronic acids, arylboronic ester and aryltrifluoroborate salt. This one-pot green method does not require copper salt, base, and intermediate isolation. Halogen-bearing chalcones, dibenzylideneacetones and arylalkyl enones were synthesized in good yields. This journal is
- Vellakkaran, Mari,Andappan, Murugaiah M. S.,Nagaiah, Kommu
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p. 45490 - 45494
(2014/12/10)
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- Synthesis and crystal structure of chalcones as well as on cytotoxicity and antibacterial properties
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A series of chalcones derivatives were synthesized and evaluated for cytotoxic and antibacterial activities in vitro. These modifications changed their bioactivity profile and indicated a combination of SAR analysis toward the substituents in rings A and
- Wu, Jianzhang,Wang, Cong,Cai, Yuepiao,Peng, Jing,Liang, Donglou,Zhao, Yunjie,Yang, Shulin,Li, Xiaokun,Wu, Xiaoping,Liang, Guang
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experimental part
p. 444 - 452
(2012/08/28)
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- Chalcones as promising pesticidal agents against diamondback moth (Plutella xylostella): Microwave-assisted synthesis and structure-activity relationship
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A series of chalcones (A-CH=CH-CO-B) were synthesized under microwave irradiation, and for the first time their pesticidal activity against diamondback moth (Plutella xylostella) was evaluated to identify the promising lead structures. The structure-activity relationship (SAR) analysis revealed that electron-withdrawing substituents on ring A of chalcone provided good pesticidal agents, whereas, ring B can bear either electron-withdrawing or electron-releasing substituents. Moreover, compound 22 having para-Cl substitution on ring A as well on ring B showed maximum activity with LC 50 value of 170.24 μg mL-1. Springer Science+Business Media, LLC 2011.
- Kumar, Rakesh,Sharma, Prabha,Shard, Amit,Tewary, Dhananjay Kumar,Nadda, Gireesh,Sinha, Arun Kumar
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experimental part
p. 922 - 931
(2012/08/14)
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- Design, synthesis, and biological evaluation of chalcone oxime derivatives as potential immunosuppressive agents
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A series of deoxybenzoin oximes were recently reported as potent immunosuppressive agents by our group. In order to continue the original research for potential immunosuppressive agents with high efficacy and low toxicity, we synthesized a series of new c
- Luo, Yin,Song, Ran,Li, Yao,Zhang, Shuai,Liu, Zhi-Jun,Fu, Jie,Zhu, Hai-Liang
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supporting information; experimental part
p. 3039 - 3043
(2012/06/04)
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- Stereoselective synthesis of γ,δ-unsaturated β-amino sulfones from ellman's N-tert-butylsulfinyl ketimines and methyl Phenyl sulfone
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A practical and straightforward approach for the highly stereoselective synthesis of γ,δ-unsaturated β-amino sulfones by nucleophilic (phenylsulfonyl)methylation of N-tert-butylsulfinyl ketimines with methyl phenyl sulfone was achieved. With lithium bis(trimethylsilyl)amide as the base, the corresponding sulfone-stabilized carbanion derived from methyl phenyl sulfone can be transferred to (S)-α,β-unsaturated N-tert-butylsulfinyl ketimines in very good yields and with high diastereoselectivities. Electron-withdrawing or electron-donating substituents on the aryl rings of (S)-α,β-unsaturated N-tert-butylsulfinyl ketimines did not exert a significant effect on the outcome of the diastereoselective nucleophilic (phenylsulfonyl) methylation.
- Zhang, Hua,Li, Ya,Xu, Fanghui,Ren, Xinfeng,Wang, Le,Sun, Zhihua,Zhou, Pei
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p. 2485 - 2490,6
(2012/12/12)
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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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- Hepatocyte growth factor pathway activators in chronic obstructive pulmonary disease
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Methods are provided for treating chronic obstructive pulmonary diseases such as emphysema using compounds that activate the signaling pathways of hepatocyte growth factor.
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- Substituent effect investigation of 3-(2, 4-dichlorophenyl)-1-(4′-X- phenyl)-2-propen-1-one. Part 1. Correlation analysis of 13C NMR chemical shifts
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A series of substituted chlorinated chalcones namely, 3-(2,4- dichlorophenyl)-1-(4′-X-phenyl)-2-propen-1-one, have been synthesized, X being H, NH2, OMe, Me, F, Cl, CO2Et, CN, and NO 2. Dual substituent parameter (DSP) mod
- Perjessy,Al-Amood,Fadhil,Pronayova
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supporting information; experimental part
p. 140 - 146
(2011/09/20)
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- Design, synthesis, and bioactivities screening of a diaryl ketone-inspired pesticide molecular library as derived from natural products
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Three natural products, 1,5-diphenylpentan-1-one, 1,5-diphenylpent-2-en-1-one, and 3-hydroxy-1,5-diphenylpentan-1-one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as 'pharmacophores', a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)-1-(2,4-dichlorophenyl)-3-(furan-2-yl)- -prop-2-en-1-one (III2) was 1.20mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.
- Zhang, Hong,Jin, Hong,Ji, Lan-Zhu,Tao, Ke,Liu, Wei,Zhao, Hao-Yu,Hou, Tai-Ping
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experimental part
p. 94 - 100
(2012/06/01)
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- One-pot two-step oxidative cleavage of 1,2-arylalkenes to aryl ketones instead of arylaldehydes in an aqueous medium: A complementary approach to ozonolysis
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A new approach has been developed for a one-pot and selective oxidative cleavage of aryl- and 1,2-diarylalkenes leading to one-carbon shorter aryl ketones; thereby, providing a complementary approach to classical ozonolysis. The methodology was applicable to diverse aromatic and polyaromaticarylalkenes bearing electron-donating or -withdrawing groups on the aromatic ring. The protocol also provided a useful one-pot oxidative cleavage-condensation sequence, which could potentially have important applications in natural product total synthesis. A one-pot, two-step approach has been achieved for the oxidative cleavage of 1,2-disubstituted arylalkenes into the corresponding aryl ketones instead of arylaldehydes (see scheme; NIS = N-iodosuccinimide; CTAB = cetyltrimethylammonium bromide; PDC/TBHP = pyridinium dichromate/tert-butyl hydroperoxide). The methodology also led to a valuable one-pot oxidative cleavage-condensation reaction that has widespread utility in the total synthesis of natural products.
- Sharma, Naina,Sharma, Abhishek,Kumar, Rakesh,Shard, Amit,Sinha, Arun K.
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supporting information; experimental part
p. 6025 - 6032
(2011/02/23)
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- Antimalarial alkoxylated and hydroxylated chalones: Structure-activity relationship analysis
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Chalcones with 2′,3′,4′-trimethoxy, 2′,4′-dimethoxy, 4′-methoxy, 4′-ethoxy, 2′,4′-dihydroxy, and 4′-hydroxy groups on ring B were synthesized and evaluated in vitro against Plasmodium falciparum (K1) in a [3H] hypoxanthine uptake assay. The other ring A was quinoline, pyridine, naphthalene, or phenyl rings with electron-donating or electron-withdrawing substituents of varying lipophilicities. Trimethoxy 6 and 27, dimethoxy 7, 8, 29, and methoxy 31 analogues had good in vitro activities (IC50 5μM). 3-Quinolinyl ring A derivatives were well represented among the active compounds. Hydroxylated chalcones were less active than the corresponding alkoxylated analogues. When evaluated in vivo, 8 and 208 were comparable to chloroquine in extending the lifespan of infected mice. Multivariate data analysis showed that in vitro activity was mainly determined by the properties of ring B. Quantitative structure - activity relationship models with satisfactory predictive ability were obtained for various B ring chalcones using projections to latent structures. A model with good predictability was proposed for 19 active chalcones. Size and hydrophobicity were identified as critical parameters.
- Liu,Wilairat,Go
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p. 4443 - 4452
(2007/10/03)
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