- Synthesis of new chromeno-carbamodithioate derivatives and preliminary evaluation of their antioxidant activity and molecular docking studies
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New chromeno carbamodithioates (7a-i), have been synthesized from 2, 3-dimethyl-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one (5), carbondisulphide and commercially available acyclic and cyclic secondary amines in acetonitrile with good to excellent yields. The free radical scavenging activity of novel chromone-carbamodithioate analogues was quantitatively estimated by spectrophotometric method. Whereas, molecular docking studies were performed with the active site of cyclooxygenase-2 to identify hydrogen bonding, hydrophobic and ionic interactions between protein and ligands. The compounds 7g and 7h demonstrated potent antioxidant activity with IC50 of 1.405?±?0.019?mM and 1.382?±?0.35?mM respectively compared to Ascorbic acid.
- Bandari, Sampath Kumar,Kammari, Bal Raju,Madda, Jyothi,Kommu, Nagaiah,Lakkadi, Arunapriya,Vuppala, Srimai,Tigulla, Parthasarathy
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Read Online
- Determining Essential Requirements for Fluorophore Selection in Various Fluorescence Applications Taking Advantage of Diverse Structure-Fluorescence Information of Chromone Derivatives
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Herein, we report our work exploring the essential requirements for fluorophore selection during the development of various fluorescence applications. We assembled a library of chromone-derived fluorophores with diverse structure-fluorescence properties, which allowed us to choose the fluorophore pairs with similar structures but differing fluorescence properties and compared the performance of the selected fluorophore pairs in three types of commonly used fluorescence applications. We found that the selection standard of a suitable fluorophore is variable depending on the application. (1) In fluorescence imaging, fluorophores with strong and constant fluorescence under various conditions, such as a large pH range, are preferred. Notably, (2) in the detection of bioactive species, fluorophores with relatively lower fluorescence quantum yield favor the detection sensitivity. Furthermore, (3) in enzymatic assays employing fluorescence, the key parameter is the binding affinity between the fluorophore and the enzyme.
- Chen, Yikun,Gao, Yongxin,He, Yujun,Zhang, Gang,Wen, Hui,Wang, Yuchen,Wu, Qin-Pei,Cui, Huaqing
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p. 1001 - 1017
(2021/01/09)
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- Exploring efficacy of natural-derived acetylphenol scaffold inhibitors for α-glucosidase: Synthesis, in vitro and in vivo biochemical studies
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The discovery of novel α-glucosidase inhibitors and anti-diabetic candidates from natural or natural-derived products represents an attractive therapeutic option. Here, a collection of acetylphenol analogues derived from paeonol and acetophenone were synthesized and evaluated for their α-glucosidase inhibitory activity. Most of derivatives, such as 9a–9e, 9i, 9m–9n and 11d–1e, (IC50 = 0.57 ± 0.01 μM to 8.45 ± 0.57 μM), exhibited higher inhibitory activity than the parent natural products and were by far more potent than the antidiabetic drug acarbose (IC50 = 57.01 ± 0.03 μM). Among these, 9e and 11d showed the most potent activity in a non-competitive manner. The binding processes between the two most potent compounds and α-glucosidase were spontaneous. Hydrophobic interactions were the main forces for the formation and stabilization of the enzyme - acetylphenol scaffold inhibitor complex, and induced the topography image changes and aggregation of α-glucosidase. In addition, everted intestinal sleeves in vitro and the maltose loading test in vivo further demonstrated the α-glucosidase inhibition of the two compounds, and our findings proved that they have significant postprandial hypoglycemic effects.
- Dong, Qingjian,Li, Ding,Liu, Ting,Liu, Zhigang,Yu, Xiao,Zhang, Fan
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supporting information
(2020/10/02)
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- Biocatalytic Friedel–Crafts Acylation and Fries Reaction
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The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C?C bond formation methods.
- Schmidt, Nina G.,Pavkov-Keller, Tea,Richter, Nina,Wiltschi, Birgit,Gruber, Karl,Kroutil, Wolfgang
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p. 7615 - 7619
(2017/06/13)
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- Natural products as sources of new fungicides (II): antiphytopathogenic activity of 2,4-dihydroxyphenyl ethanone derivatives
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A series of 17 simple 1-(2,4-dihydroxyphenyl) ethanones were synthesised, and their structures characterised by 1H, 13C NMR and ESI-MS. Their in vitro antifungal activities were evaluated against five phytopathogenic fungi including Glomerella cingulate, Botrytis cirerea, Fusarium graminearum, Curvularia lunata and Fusarium oxysporum f. sp. vasinfectum by the mycelial growth inhibition assay. Compounds 2g and 2h exhibited broad-spectrum inhibitory activity against the mycelial growth of the tested pathogens with IC50 values in the range of 16-36 g/mL, and in particular being more active to G. cingulate, with IC50 values of 16.50 and 19.25 g/mL, respectively, than the other pathogens. Preliminary SAR indicated that an α,β-unsaturated ketone unit of the alkyl chain of the compounds is the structure requirement for fungicidal action. The results suggested that 2g and 2h may be promising leads in the development of new antifungal agents.
- Nandinsuren, Tseden,Shi, Wei,Zhang, An-Ling,Bai, Yu-Bin,Gao, Jin-Ming
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supporting information
p. 1166 - 1169
(2016/04/20)
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- Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
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Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ~ 205.19, λab ~ 350 nm, λem ~ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is
- Miao, Jianzhuang,Cui, Huaqing,Jin, Jing,Lai, Fangfang,Wen, Hui,Zhang, Xiang,Ruda, Gian Filippo,Chen, Xiaoguang,Yin, Dali
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supporting information
p. 881 - 884
(2015/02/19)
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- Synthesis, antiproliferative, and c-Src kinase inhibitory activities of 4-oxo-4H-1-benzopyran derivatives
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A new class of 4-oxo-4H-1-benzopyran derivatives were synthesized and their antiproliferative activity examined against a panel of three human cancer cell lines, that is, breast carcinoma (MDA-MB-468), ovarian adenocarcinoma (SK-OV-3), and colorectal adenocarcinoma (HT-29). Two compounds, that is, 3-hexyl-7,8-dihydroxy-4-oxo-4H-1-benzopyran and (E)-ethyl 3-(7-methoxy-4-oxo-4H-1-benzopyran-3-yl)acrylate were found to be potent against all three cancer cell lines studied at 50 μM concentration. Also, the inhibitory potency of the compounds was evaluated against active Src kinase. A few of these compounds exhibited modest Src kinase inhibitory activity (IC50 = 52-57 μM). Structure-activity relationship studies with respect to the nature and position of substituents on the lead compounds could be further exploited for the design and development of more potent antiproliferative agents and/or Src kinase inhibitors.
- Chand, Karam,Tiwari, Rakesh K.,Kumar, Sumit,Shirazi, Amir Nasrolahi,Sharma, Sweta,Van Der Eycken, Erik V.,Parmar, Virinder S.,Parang, Keykavous,Sharma, Sunil K.
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p. 562 - 572
(2015/03/30)
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- Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists
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Compound 1 (IC50 = 35.2 ± 7.2 μM), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 ± 0.1 μM. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity.
- Liu, Peng,Xu, Xing,Chen, Lili,Ma, Lei,Shen, Xu,Hu, Lihong
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p. 1596 - 1607
(2014/03/21)
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- Synthesis of novel 7-(heteryl/aryl)chromones via Suzuki coupling reaction
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A series of new 7-heteroaryl and arylchromones 6a-l were synthesized in moderate to good yields by the Suzuki reaction of the triflate (pseudo halide) 5 and a variety of heteroaryl and aryl boronic acids. The resulting products may be used as precursors for synthesis of potentially relevant compounds. The structures of all synthesized compounds were established based on IR, 1H NMR, 13C NMR, and DIPMS.
- Anitha, Naredla,Reddy, K. Venugopal,Rao, Y. Jayaprakash
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p. 129 - 132
(2014/07/07)
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- Arylalkyl ketones, benzophenones, desoxybenzoins and chalcones inhibit TNF-α induced expression of ICAM-1: Structure-activity analysis
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The interaction between leukocytes and the vascular endothelial cells (EC) via cellular adhesion molecules plays an important role in the pathogenesis of various inflammatory and autoimmune diseases. Small molecules that block these interactions have been targeted as potential therapeutic agents against acute and chronic inflammatory diseases. In an effort to identify potent intercellular cell adhesion molecule-1 (ICAM-1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism for their ICAM-1 inhibitory activities. The most active compound was found to be 79. A large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones as well as their analogs (54 in total) were synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated a possible mechanism of their ICAM-1 inhibitory activities. The most active compound was found to be 79. Copyright
- Kumar, Sarvesh,Reddy L, Chandra Shekhar,Kumar, Yogesh,Kumar, Amit,Singh, Brajendra K.,Kumar, Vineet,Malhotra, Shashwat,Pandey, Mukesh K.,Jain, Rajni,Thimmulappa, Rajesh,Sharma, Sunil K.,Prasad, Ashok K.,Biswal, Shyam,Van Der Eycken, Erik,Depass, Anthony L.,Malhotra, Sanjay V.,Ghosh, Balaram,Parmar, Virinder S.
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experimental part
p. 368 - 377
(2012/07/31)
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- 2-Hydroxy-4-n-butoxy-5-bromo propiophenone Thiosemicarbazone as Spectrophotometric Reagent for Iron
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A simple, sensitive and specific spectrophotometric method has been developed for the determination of iron(II) in benzene. The metal ion reacts with 2-hydroxy-4-n-butoxy-5-bromo propiophenone thiosemicarbazone (HBBrPT) forming a dark red coloured complex in the pH range 5.0-9.0. The complex shows maximum absorption at 470 nm. Beer's law is obeyed in the range 13.96 μg/mL. The molar absorptivity and Sandell's sensitivity are found to be 2845 L mol-1 cm-1 and 0.01962 μg cm-2, respectively. The solid complex have been isolated and characterized on the basis of elemental analysis, UV, IR, NMR and mass spectra. 2-Hydroxy-4-n-butoxy-5-bromo propiophenone thiosemicarbazone is found to be a selective and strong chelating agent for iron. The results deduced from Job's method of continuous variation, the mole ratio and the slope ratio method showed that metal: ligand ratio in the complex to be 1:2. The stability constant of the complex found to be 1.22 × 107. The free energy change for the complex formation reaction is found to be-9.989 K cal/mol at 35°C. The complex is fairly stable for about 24 h and up to 55°C.
- Parikh,Patel,Patel
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body text
p. 2805 - 2810
(2010/11/04)
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- Process for the synthesis of alkylresorcinols
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The invention provides a process for the production of 4-(C2-C16)alkylresorcinol. 4-(C2-C16)alkylresorcinol is produced by reacting resorcinol with a (C2-C16)alkyloic acid in the presence of a zinc chloride catalyst to produce an intermediate comprising a 4-(C2-C16)acylresorcinol and zinc ions. Then the intermediate is adjusted such that the zinc ion content is from about 0.1 to about 150 parts per million based on the weight of the intermediate to form an adjusted intermediate. Then the produced 4-(C2-C16)acylresorcinol is hydrogenated in the presence of the zinc ions and a base metal hydrogenation catalyst to produce a crude product comprising 4-(C2-C16)alkylresorcinol, which may thereafter be isolated.
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Page/Page column 2-3
(2008/06/13)
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- Nematic phase formed by V-shaped molecules
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In the paper there are presented synthesis and properties of new banana-shaped molecules that are ester resorcinol derivatives. The compounds with lateral alkyl substituent at the 4-position of the resorcinol ring exhibit the liquid crystalline nematic phase. Some of the synthesised compounds are able to induce the anticlinic S*CA phase that proves their bent molecular shape.
- Szydlowska, Jadwiga,Matraszek, Joanna,Mieczkowski, Jozef,Gorecka, Ewa,Pociecha, Damian
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p. 107 - 115
(2007/10/03)
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- Synthesis and lipase-mediated stereoselective deacetylation of (±)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones
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Six (±)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding aliphatic acid leading to the formation of 2,4-dihydroxyphenyl alkyl ketones, which upon monomethylation and hydroxymethylation, followed by acetylation afforded the racemic acetoxymethylated compounds in 17-30% overall yields. Candida rugosa lipase-catalyzed deacetylation of (±)-3-acetoxymethylchromanones in diisopropyl ether exhibited fairly moderate enantioselectivity.
- Poonam,Prasad, Ashok K,Azim, Abul,Kumar, Rajesh,Jain, Subhash C,Parmar, Virinder S,Olsen, Carl E,Errington, William
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p. 7395 - 7402
(2007/10/03)
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- FORMATION OF BF2 CHELATES IN ACYLATION OF RESORCINOL AND 4-CYCLOHEXYLRESORCINOL WITH CARBOXYLIC ACIDS IN THE PRESENCE OF BF3-ETHER COMPLEX
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New chelates, 1-acyl-2-difluoroboroxy-4-hydroxybenzene and 1-acyl-2-difluoroboroxy-4-hydroxy-5-cyclohexylbenzene, were synthesized by acylation of resorcinol and 4-cyclohexylresorcinol with acetic, propionic, butyric, valeric, and phenylacetic acids, catalyzed by BF3*OEt2.On heating with aqueous alcohol, the chelates are hydrolyzed to the corresponding ketones.
- Panasenko, A. I.,Polyanskaya, N. L.,Starkov, S. P.
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p. 611 - 613
(2007/10/02)
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- Synthese von 4-Alkoxy-2-hydroxyphenylketoximen als Metallextraktions-Reagenzien
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The C-Acylation (Friedel-Crafts reaction) of resorcinol with aluminium chloride, the monoetherification in 4-position of the resulting 2,4-dihydroxyphenylketones, and the preparation of oximes (8, 9, 10, 11) from this ketones were investigated.The compounds obtained are characterized by elemental analysis, and the i.r., u.v. and 1H-n.m.r. spectra are discussed.Solubility data of some oximes are determined in water, octane and toluene.The extraction properties for copper-(II)-and iron-(III)-ions are measured by isotope methods in relation to the extragent structure, the extraction time and the pH-range.
- Beger, J.,Binte, H.-J.,Brunne, L.,Neumann, R.
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p. 269 - 277
(2007/10/02)
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- Antifungal Activity of 2,4-Dihydroxyacylophenones and Related Compounds
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The antifungal activity of 2,4-dihydroxyacylophenones and related compounds against Trichophyton spp. and other fungi were investigated to determine their structure-activity relationships.The activity of these compounds was found to be closely related to the length of the acyl and alkyl substituents attached to the 1,3-dihydroxybenzene moiety.In addition, differences in activity were observed depending on the position of the alkyl substituents and on the number of substituents attached to the 1,3-dihydroxybenzene moiety.Some compounds tested showed potent antifungal activity against Trichophyton spp. and other fungi that was more active than amphotericin B.
- Mizobuchi, Shigeyuki,Sato, Yuko
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p. 1327 - 1334
(2007/10/02)
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