- 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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- Rational Engineered C-Acyltransferase Transforms Sterically Demanding Acyl Donors
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The biocatalytic Friedel-Crafts acylation has been identified recently for the acetylation of resorcinol using activated acetic acid esters for the synthesis of acetophenone derivatives catalyzed by an acyltransferase. Because the wild-type enzyme is limited to acetic and propionic derivatives as the substrate, variants were designed to extend the substrate scope of this enzyme. By rational protein engineering, the key residue in the active site was identified which can be replaced to allow binding of bulkier acyl moieties. The single-point variant F148V enabled the transformation of previously inaccessible medium chain length alkyl and alkoxyalkyl carboxylic esters as donor substrates with up to 99% conversion and up to >99% isolated yield.
- ??d?o-Dobrowolska, Anna,Hammerer, Lucas,Pavkov-Keller, Tea,Gruber, Karl,Kroutil, Wolfgang
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p. 1094 - 1101
(2020/01/21)
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- Synthesis and evaluation of aromatic methoxime derivatives against five postharvest phytopathogenic fungi of fruits. Main structure–activity relationships
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The antifungal activity of a library of twenty-four aromatic methoximes was examined against five representative postharvest phytopathogenic fungi. The panel included Penicillium digitatum, Penicillium italicum, Rhizopus stolonifer, Botrytis cinerea and Monilinia fructicola, all of which cause relevant economic losses worldwide as a result of affecting harvested fruits. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were defined and the main structure–activity relationships were determined. Although other congeners were more potent, drug likeliness considerations pointed to the methoxime derived from 2,4-dihydroxypropiophenone as the compound with the most suitable profile. The morphology of the colonies of the fungal strains treated with the methoxime was examined microscopically and the compound was also tested in freshly harvested peaches and oranges, exhibiting promising control profiles in both fruits, similar to those of the commercial agents Imazalil and Carbendazim.
- Cortés, Iván,di Liberto, Melina G.,Kaufman, Teodoro S.,Derita, Marcos G.,Bracca, Andrea B.J.
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- Preparation method of 4-alkylresorcinol
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The invention discloses a preparation method of 4-alkylresorcinol. The preparation method comprises the steps: carrying out a reaction on resorcinol and alkyl acid to prepare acyl resorcinol, and then, catalyzing a hydrogenation reaction to obtain 4-alkylresorcinol. By using the method, the dosages of a catalyst and alkyl groups are controlled in an acylation process, so that the yield is remarkably increased, byproducts are reduced, and the production cost is reduced; and hydrogen reduction is adopted in a reduction process, and a high-toxicity and high-pollution zinc amalgam reducing agent is prevented from being used, so that the preparation method is green and environment-friendly; and the aftertreatment is simple, the prepared product is high in purity, the total yield of the two steps reaches up to 77%, and the preparation method has a remarkable significance for industrial production of 4-alkylresorcinol.
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Paragraph 0033; 0034
(2018/05/01)
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- Primulin derivative as well as synthesis method and application of primulin derivative
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The invention discloses a primulin derivative with antibacterial activity shown as the structural general formula (I), wherein R is selected from C2-C20 alkyls. The primulin derivative is prepared from raw materials including m-dihydroxybenzene and a fatty acid derivative by the steps: carrying out Friedel-Crafts acylation and methylation to synthesize a paeonol derivative, and carrying out oxidization after carrying out carbonyl reduction. The primulin derivative has good antibacterial activity and can be used as a potential antibacterial agent.
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Paragraph 0023
(2018/01/11)
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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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- 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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- A photochemical route to 2-substituted benzo[b]furans
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2-Substituted benzo[b]furans were synthesized by a one-step metal-free photochemical reaction between 2-chlorophenol derivatives and terminal alkynes by tandem formation of an aryl-C and a C-O bond via an aryl cation intermediate. The mild conditions and the application to chlorophenols rather of the more expensive bromo or iodo analogues makes this procedure environmentally convenient.
- Protti, Stefano,Fagnoni, Maurizio,Albini, Angelo
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experimental part
p. 6473 - 6479
(2012/10/08)
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- SKIN LIGHTENING COMPOSITIONS AND METHODS
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Skin lightening/even toning compositions are provided for reducing skin pigmentation of normal skin and for lightening hyper-pigmented skin said compositions comprising (i) highly purified hexylresorcinol which is substantially free or resorcinol, (ii) optionally, at least one other skin lightening agent, and (iii) a dermatologically acceptable carrier.
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Page/Page column 19-21
(2009/01/24)
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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 3
(2008/06/13)
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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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- 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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- 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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