- A Nouvel Route to Resorcinols
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Hydroxylation of para-alkylated or 2,6-dialkylated phenols by hydrogen peroxide in SbF5-HF yields resorcinols, the electrophile reacting with the O-protonated substrate.
- Gesson, Jean-Pierre,Jacquesy, Jean-Claude,Jouannetaud, Marie-Paule
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- Total Syntheses of 4′,6′-Dimethoxy-2'-Hydroxy-3′,5′-Dimethylchalcone Derivatives
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Chalcone derivatives afford several pharmacological activities. However, a general synthetic method for 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (DMC) derivatives has not been reported thus far. To address this, the preparation of 4',6'-dimethoxy-2'-hydroxy-3',5'-dimethylchalcone (MDMC) derivatives, modified compounds of DMC, in excellent overall yields is reported herein. These compounds have recently attracted growing attention due to their various pharmacological activities. Di-O-methyl-dimethylphloroacetophenone, the key intermediate containing the B-ring moiety, was fabricated by four efficient reaction steps from commercially available phloroglucinol in a 50.1% isolated yield overall. Our synthetic route, which constructs the chalcone skeleton in the final stage via a Claisen–Schmidt condensation of the key intermediate with the desired benzaldehyde derivative, can rapidly produce a vast library of DMC derivatives.
- Lee, Hana,Park, Rae Yeon,Park, Kwangyong
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- HALOGEN-SUBSTITUTED DIMETHYLCHALCONE DERIVATIVES AND PREPARATION METHOD THEREOF
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The present invention relates to dimethylchalcone (DMC) derivatives substituted with halogen and a method for producing the same. A compound according to an embodiment of the present invention is represented by chemical formula I: [Chemical Formula I]. In Formula I, R1 and R2 are the same as or different from each other, R1, and R2 are each independently selected from the group consisting of hydrogen, methoxy, and methoxy. R3, and R4 are each independently hydrogen or halogen elements, and when R3 is hydrogen, R4 R4 is any one selected from the group consisting of halogen elements R3.
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- DIMETHYLCHALCONE DERIVATIVES AND PREPARATION METHOD THEREOF
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The present invention relates to a dimethalcone (DMC) derivative and a method for producing the same. A compound according to an embodiment of the present invention is represented by chemical formula I: [Chemical Formula I]. In Formula I, R1, R2, and R3 are the same as or different from each other, R1 is a hydroxy group or a methoxy group, R2, and R3 are each independently hydrogen, deuterium, a nitro group, a hydroxyl group, a carbonyl group C1?C10, a nitro group, C1?C10 a hydroxyl group, an 'C2?C10 alkyloxy group', an aryloxy C2?C10 group, an aryloxy group, an alkylthioxy group, a silyl group, a boron group, an alkyl group or an C6?C20 aryl group. (C1?C10. The cycloalkyl group, alkenyl group, alkynyl group, aryl group, aralkyl group, aralkyl group, alkylaryl group, alkylamine group. The substituent may be substituted or unsubstituted with 1 or more substituents selected from the group consisting of an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group.
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- Discovery of Anti-TNBC Agents Targeting PTP1B: Total Synthesis, Structure-Activity Relationship, in Vitro and in Vivo Investigations of Jamunones
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Twenty-three natural jamunone analogues along with a series of jamunone-based derivatives were synthesized and evaluated for their inhibitory effects against breast cancer (BC) MDA-MB-231 and MCF-7 cells. The preliminary structure-activity relationship revealed that the length of aliphatic side chain and free phenolic hydroxyl group at the scaffold played a vital role in anti-BC activities and the methyl group on chromanone affected the selectivity of molecules against MDA-MB-231 and MCF-7 cells. Among them, jamunone M (JM) was screened as the most effective anti-triple-negative breast cancer (anti-TNBC) candidate with a high selectivity against BC cells over normal human cells. Mechanistic investigations indicated that JM could induce mitochondria-mediated apoptosis and cause G0/G1 phase arrest in BC cells. Furthermore, JM significantly restrained tumor growth in MDA-MB-231 xenograft mice without apparent toxicity. Interestingly, JM could downregulate phosphatidylinositide 3-kinase (PI3K)/Akt pathway by suppressing protein-tyrosine phosphatase 1B (PTP1B) expression. These findings revealed the potential of JM as an appealing therapeutic drug candidate for TNBC.
- Hu, Caijuan,Li, Guoxun,Mu, Yu,Wu, Wenxi,Cao, Bixuan,Wang, Zixuan,Yu, Hainan,Guan, Peipei,Han, Li,Li, Liya,Huang, Xueshi
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p. 6008 - 6020
(2021/05/06)
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- Synthesis of methylophiopogonanone a
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Ophiopogon Root (root of Ophiopogon japonicus Ker-Gawler, Liliaceae) is a crude drug used as expectorant, anti-cough and tonic in Kampo medicine (traditional Japanese medicine) as well as other traditional medicines of Asian countries. It contains characteristic homoisoflavonoids with methylated ring A. We synthesized methylophiopogonanone A (1), which is a candidate marker compound for identification test of Ophiopogon Root, from phloroglucinol in 9 steps with overall yield of 11.1%.
- Katagiri, Ryo,Kiuchi, Fumiyuki,Narukawa, Yuji,Uekusa, Yoshinori
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p. 803 - 808
(2020/10/30)
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- Biomimetic Synthesis Enables the Structure Revision of Littordials e and F and Drychampone B
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Structural reassignments for littordial E, littordial F, and drychampone B are proposed on the basis of consideration of their biosynthetic origin. The key step in the proposed biosynthesis of each of these meroterpenoids is an intermolecular hetero-Diels-Alder reaction between an o-quinone methide and caryophyllene or humulene. Biomimetic total synthesis of the natural products gave sufficient material to allow their structure revision by NMR studies.
- Vieira De Castro, Tomás,Yahiaoui, Oussama,Peralta, Ricardo A.,Fallon, Thomas,Lee, Victor,George, Jonathan H.
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p. 8161 - 8166
(2020/11/02)
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- Derivatives of Natural Product Agrimophol as Disruptors of Intrabacterial pH Homeostasis in Mycobacterium tuberculosis
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This article reports the rational medicinal chemistry of a natural product, agrimophol (1), as a new disruptor of intrabacterial pH (pHIB) homeostasis in Mycobacterium tuberculosis (Mtb). Through the systematic investigation of the structure-activity relationship of 1, scaffold-hopping of the diphenylmethane scaffold, pharmacophore displacement strategies, and studies of the structure-metabolism relationship, a new derivative 5a was achieved. Compound 5a showed 100-fold increased potency in the ability to reduce pHIB to pH 6.0 and similarly improved mycobactericidal activity compared with 1 against both Mycobacterium bovis-BCG and Mtb. Compound 5a possessed improved metabolic stability in human liver microsomes and hepatocytes, lower cytotoxicity, higher selectivity index, and similar pKa value to natural 1. This study introduces a novel scaffold to an old drug, resulting in improved mycobactericidal activity through decreasing pHIB, and may contribute to the critical search for new agents to overcome drug resistance and persistence in the treatment of tuberculosis.
- Wu, Jie,Mu, Ran,Sun, Mingna,Zhao, Nan,Pan, Miaomiao,Li, Hongshuang,Dong, Yi,Sun, Zhaogang,Bai, Jie,Hu, Minwan,Nathan, Carl F.,Javid, Babak,Liu, Gang
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p. 1087 - 1104
(2019/05/22)
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- Aurone compound and preparation method and application thereof
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The invention provides an aurone compound shown in the formula (I). Compared with the prior art, the compound has the relatively high inhibiting effect on release of PGE (prostaglandine) 2 of RAW 264.7 macrophage of a mouse induced by lipopolysaccharide, the activity is superior to ibuprofen, and the aurone compound has the anti-inflammatory related pharmacological activity.
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- Chemo-enzymatic Total Synthesis of Oxosorbicillinol, Sorrentanone, Rezishanones B and C, Sorbicatechol A, Bisvertinolone, and (+)-Epoxysorbicillinol
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The sorbicillinoids are a large family of fungal natural products, many of which possess highly challenging molecular architectures. Depending on their individual structures they exhibit strong biological activities ranging from radical scavenging and anti-infective properties to cytotoxicity. Despite the resulting strong biomedical potential of these natural products and the interest of synthetic chemists owing to their fascinating structures, many sorbicillinoids are currently not synthetically accessible, thus hampering in-depth biological characterization and structural diversification. By using recombinant oxidoreductase SorbC and readily accessible sorbicillin-type synthetic precursors, we have developed enantioselective, one-pot chemo-enzymatic routes to a broad range of sorbicillinoids, thereby establishing total syntheses of oxosorbicillinol, sorrentanone, rezishanones B and C, sorbicatechol A, bisvertinolone, and (+)-epoxysorbicillinol.
- Sib, Anna,Gulder, Tobias A. M.
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p. 14650 - 14653
(2018/10/26)
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- C-methylisoflavones and their derivatives and producing methods thereof
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The present invention biological activity at the time of compared to the rock it was recorded victims of the natural compound C - methyl isocyanate compound (compound 1) this cow [phul [phul] sample, number 6, 8 - methyl-varnish resin (compound 2) and derivatives (compounds 3 - 8) 7 - 8 to step 16 - 24% total yield from commercially available precursors to simply and efficiently copiers. Strategy in sucrose - the [khu [khu] to do reaction (Vilsmeier-a Haack reaction), prepared by methylation reactable with the acylated (Friedel-a Crafts acylation) on grow [phu [phu] [chu] - phosphonites, dog secret conference protocol (Gammill's protocol) and suzuki coupling reaction (Suzuki coupling reactions) main step has been applied. In addition, in the present invention so as to induce RAW264 LPS for compounds 1 - 8. 7 Billion NO generation number in macrophages to assaying for the ability to him. All are made from the test sample concentration depending on reduce the production NO concentration (10 μmol/L) clear cytotoxicity to cells we shall be, 10. 17 To 33. 88 Μmol/L range of IC50 Minimal inhibitory effects on the efficient value mistletoe. As an essential compound 3 (IC50 =10. 17 Μmol/L), compound 1(IC50 =13. 2 Μmol/L), compound 7(IC50 =13. 21 Μmol/L) compound 8 (IC50 =14. 67 Μmol/L) is positive controls is used as an L-a NMMA (N- Monomethyl-a L a-arginine) (IC50 =7. 82 Μmol/L) compared to the number effect significant billion mistletoe. (by machine translation)
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- First synthesis and in vitro biological assessment of isosideroxylin, 6,8-dimethylgenistein and their analogues as nitric oxide production inhibition agents
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A modular and efficient synthesis of the biologically significant C-methylisoflavones isosideroxylin (1), 6,8-dimethylgenistein (2) and their analogues (3–8) is established for the first time. The synthesis is realized in 7-8 steps in overall yields of 16%-24% from commercially inexpensive phloroglucinol and features a high yielding Vilsmeier–Haack reaction, Friedel-Crafts acylation, Gammill's protocol and Suzuki coupling as the pivotal transformations. Next, these compounds evaluated for their inhibitory potency on the production of nitric oxide (NO) in lipopolysaccharide (LPS)-activated RAW-264.7 cells as an indicator of anti-inflammatory activity. The results showed that all the compounds decreased NO production in a dose-dependent manner without marked cytotoxicity and IC50 values are found in the range of 10.17–33.88?μmol/L. Of note, compounds 3 followed by 1, 7 and 8 show comparable inhibitory activity with positive control (N-monomethyl-L-arginine, L-NMMA).
- Jung, Jong-Woon,Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
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p. 1114 - 1118
(2017/05/22)
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- Tandem Chloropalladation/Cyclization and Dearomative Cyclization toward Functionalized Tricyclic Bridged [3.2.1] Skeleton Compounds
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A palladium-catalyzed tandem reaction is reported that involves chloropalladation/cyclization and dearomative cyclization to construct a tricyclic bridged [3.2.1] carbocyclic-skeleton and oxa- and aza-skeletons. In this domino process, a level of ring strain and other competitive reactions, i.e., protonolysis, β-hydride elimination, and chlorination of the C-Pd bond, were suppressed to the lowest level under mild reaction conditions.
- Dong, Yi,Du, Nana,Li, Xueyuan,Zheng, Litao,Liu, Gang
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supporting information
p. 4110 - 4113
(2015/09/01)
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- A practical synthesis of a new series of isoflavanones
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A practical six-step synthesis of 12 methylated and hydroxylated isoflavanones was accomplished starting from readily available m-xylene. A significant improvement of this procedure included application of the simple and commercially available reagents, avoidance of expensive reagents and catalysts, simple operations and excellent yields.
- Liu, Ju Na,Ban, Shu Rong,Xie, Hong Yu,Li, Qing Shan
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experimental part
p. 907 - 910
(2012/09/10)
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- PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
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The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.
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- Synthesis and biological activity of flavanone derivatives
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A series of new flavanone derivatives of farrerol was synthesized by a convenient method. The in vitro anti-tumor activity of these compounds was evaluated against human Bel-7402, HL-60, BGC-823 and KB cell lines, the protein tyrosine kinase (PTK) inhibitor activity was also tested. Their cytoprotective activity was tested using hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells. Their in vitro anti-atherosclerosis activity was tested on vascular smooth muscle cells by the MTT method using tetrandrine as a positive contrast drug. The structures of all compounds synthesized were confirmed by 1H, 13C NMR and ESI-MS. Most of the compounds exhibited good pharmacological activity and the preliminary structure-activity relationships were described.
- Shi, Lei,Feng, Xiu E,Cui, Jing Rong,Fang, Lian Hua,Du, Guan Hua,Li, Qing Shan
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scheme or table
p. 5466 - 5468
(2011/01/03)
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- Asymmetric cyclization of 2′-hydroxychalcones to flavanones: Catalysis by chiral Bronsted acids and bases
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The asymmetric cyclization of 2′-hydroxychalcones to flavanones is a basic, enzyme-catalyzed step in the biosynthesis of flavonoid natural products, but poses a long-standing problem for asymmetric catalysis with small molecule catalysts. Earlier claims concerning the realization of an asymmetric flavanone synthesis by means of camphorsulfonic acid as chiral Bronsted acid catalysts were reinvestigated using accurate HPLC methods for quantification of enantiomer ratios. The previous claims of asymmetric induction were thus shown to be untenable. On the other hand, cinchona alkaloids serve as chiral Bronsted base mediators for the asymmetric cyclization of either 6′-substituted 2′-hydroxychalcones or 2′,6′- dihydroxychalcones. 2′,6′-Dihydroxy-4,4′-dimethoxychalcone, for instance, cyclized to give the naturally occurring naringenin-4′,7- dimethyl ether in up to 64 % ee at 81 % conversion. The catalysis shows a marked dependency of the enantiomeric excess of the product on the catalyst, solvent and reactant concentration. Based on these successful examples of asymmetric cyclizations of 2′-hydroxychalcones to flavanones, requirements for more active asymmetric catalysts can be defined. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Dittmer, Claudia,Raabe, Gerhard,Hintermann, Lukas
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p. 5886 - 5898
(2008/04/13)
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- A Novel Synthesis of 1-(2,4,6-Trihydroxy-3,5-dimethylphenyl)ethanone (Di-C-methylphloracetophenone) and Two New Non-Aromatic C-Benzylated Derivatives
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The synthesis of the title compound 1e was achieved by an easy three-step procedure from 1,3,5-benzenetriol (1a, phloroglucinol).Compound 1a was C-methylated using MeI.The crude mixture obtained was acetylated to give 1d which was converted into 1e using BF3*AcOH complex.Benzylation of the latter with benzyl chloride afforded the new non-aromatic compound 2.Reaction of 2 with NaOH and benzoyl chloride (Scheme 1) gave the new compound 4.Its structure was established by X-ray analysis. - Keywords: Acetophenone / Di-C-methylphloracetopheneone
- Hauteville, Marcelle,Stomberg, Rolf,Gaillard, Pascale,Duclos, Marie-Christine
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p. 1707 - 1710
(2007/10/02)
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- Pharmaceutical compositions containing compounds with a flavanone skeleton, process for the preparation of the said compound and novel compounds obtained
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Compounds with a flavanone skeleton having the formula I STR1 in which R1 and R2, which may be the same or different, represent hydrogen, hydroxyl, methoxyl, thiomethyl, amino or substituted amino, are endowed with expectorant, mucolytic, mucopoietic, choleretic and hypolipaemia-producing activity.
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- Enol Ethers, XIV. Acylation of Keto Enol Ethers with Malonyl Dichloride - A New Synthesis of Phloroglucinols
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Phloroglucinols 4 and/or 4-hydroxy-2H-pyran-2-ones 5 are formed from keto enol ethers 1 and malonyl dichloride (2a) in high yields.Since the pyranones 5 can be smoothly converted into phloroglucinols, the reaction of 1 with 2a represents a new, facile synthetic route to phloroglucinols.The reaction proceeds via formation of a chloro carbonyl ketene 8 and its subsequent reaction with 1.The product ratio 4:5 is rationalized in terms of substituent effects in the enol ether substrate.
- Effenberger, Franz,Schoenwaelder, Karl-Heinz
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p. 3270 - 3279
(2007/10/02)
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