- Efficient synthesis of polycycles bearing prenylated, geranylated, and farnesylated citrans: Application to 3′-prenylrubranine and petiolin D regioisomer
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Efficient synthetic routes for biologically interesting polycycles with prenylated, geranylated, and farnesylated citrans were developed from several trihydroxybenzenes with prenyl, geranyl, and farnesyl groups on the benzene rings. Ethylenediamine diacet
- Wang, Xue,Lee, Yong Rok
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- Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin
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The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug
- Fu, Xuewen,Lu, Xiaoxia,Wang, Chun,Wen, Yongju,Xiong, Wei,Zhang, Guolin,Zhang, Jichao
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p. 1117 - 1124
(2022/02/16)
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- Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones
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American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.
- Escobar, Gustavo,González, Luis A.,Qui?ones, Wiston,Robledo, Sara,Upegui, Yulieth
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- PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
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The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
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Paragraph 00348; 00372
(2021/12/08)
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- Convenient and efficient total synthesis method for icaritin and derivatives of icaritin
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The invention belongs to the field of natural medicine synthesis and particularly relates to a convenient and efficient total synthesis method for icaritin and derivatives of icaritin. The specific technical scheme is as follows: 2'-hydroxyacetophenone and benzaldehyde are used as raw materials, firstly, isopentene groups are introduced in aromatic rings of raw materials under the catalysis of anorganic polyacid metal ion complex, a flavonol framework is constructed under mild and green conditions, and an isopentenyl flavone compound comprising the icaritin and derivatives of icaritin is further synthesized. The method effectively overcomes the limitation of poor substrate solubility and poor regioselectivity when flavone is constructed firstly and then isopentene groups are introduced, the problems of frequent introduction and removal of protecting groups in a conventional isopentenylation method are solved, and the synthesis route is greatly simplified; and meanwhile, the problems of complex products and more byproducts in an isopentene group rearrangement method are solved. The total synthesis method provided by the invention is mild in condition, convenient to operate, high intotal yield and suitable for mass production of the isopentenyl flavone compound.
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Paragraph 0063; 0069-0073
(2020/02/06)
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- 3-site piperazinylchalcone derivative, and pharmaceutical composition and applications thereof
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The present invention relates to a 3-site piperazinylchalcone derivative, which has a structure formula represented by a general formula (I) defined in the specification, wherein R is one selected from a substituted or unsubstituted phenyl group, a fused ring group and substituted or a unsubstituted heterocyclic group. The present invention further provides a pharmaceutical composition of the3-site piperazinylchalcone derivative, and applications thereof. According to the present invention, the results of the activity test based on P-gp target show that the 3-site piperazinylchalcone derivative and the pharmaceutical composition have good activity, can provide practical value in the treatment of the multidrug resistance of tumors, can solve the technical problems of difficult synthesis and high cost in the synthesis of the reversing agent used in the prior art, and is meaningful.
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Paragraph 0049-0051; 0054; 0055
(2019/02/04)
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- Design, synthesis and biological evaluation of chalcones as reversers of P-glycoprotein-mediated multidrug resistance
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Overexpression of P-glycoprotein (P-gp) is one of the major causes for multidrug resistance (MDR), which has become a major obstacle in cancer therapy. One hopeful approach to reverse the MDR is to develop inhibitors of P-gp in expression and/or function. Here, we designed and synthesized a series of chalcone derivatives as P-gp inhibitors and evaluated their potential reversal activities against MDR. Among them, the most active compound MY3 had little intrinsic cytotoxicity and showed the highest activity (RF = 50.19) in reversing DOX resistance in MCF-7/DOX cells. Further studies demonstrated that MY3 could increase intracellular accumulation of DOX and inhibit expression of P-gp at mRNA and protein levels. More importantly, MY3 significantly enhanced the efficacy of DOX against the tumor xenografts bearing MCF-7/DOX cells with the precondition of unchanged body weight. Therefore, MY3 might represent a promising lead to develop MDR reversal agents for cancer chemotherapy.
- Yin, Huanhuan,Dong, Jingjing,Cai, Yingchun,Shi, Ximeng,Wang, Hao,Liu, Guixia,Tang, Yun,Liu, Jianwen,Ma, Lei
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p. 350 - 366
(2019/07/19)
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- Hits-to-lead optimization of the natural compound 2,4,6-trihydroxy-3-geranyl-acetophenone (thga) as a potent lox inhibitor: Synthesis, structure-activity relationship (sar) study, and computational assignment
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A new series of 2,4,6-trihydroxy-3-geranyl-acetophenone (tHGA) analogues were synthesized and evaluated for their lipoxygenase (LOX) inhibitory activity. Prenylated analogues 4a-g (half maximal inhibitory concentration (IC50) values ranging from 35 μM to 95 μM) did not exhibit better inhibitory activity than tHGA (3a) (IC50 value: 23.6 μM) due to the reduction in hydrophobic interaction when the alkyl chain length was reduced. One geranylated analogue, 3d, with an IC50 value of 15.3 μM, exhibited better LOX inhibitory activity when compared to tHGA (3a), which was in agreement with our previous findings. Kinetics study showed that the most active analogue (3e) and tHGA (3a) acted as competitive inhibitors. The combination of in silico approaches of molecular docking and molecular dynamic simulation revealed that the lipophilic nature of these analogues further enhanced the LOX inhibitory activity. Based on absorption, distribution, metabolism, excretion, and toxicity (ADMET) and toxicity prediction by komputer assisted technology (TOPKAT) analyses, all geranylated analogues (3a-g) showed no hepatotoxicity effect and were biodegradable, which indicated that they could be potentially safe drugs for treating inflammation.
- Ng, Chean Hui,Rullah, Kamal,Abas, Faridah,Lam, Kok Wai,Ismail, Intan Safinar,Jamaludin, Fadzureena,Shaari, Khozirah
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- Cnidimonins A-C, Three Types of Hybrid Dimer from Cnidium monnieri: Structural Elucidation and Semisynthesis
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Three pairs of racemic dimers, (±)-cnidimonins A-C (1-3), were isolated from the fruits of Cnidium monnieri. They represent novel hybrid-dimerization patterns of coumarin skeleton with structurally diverse units (flavonol, benzofuran, and chromone) via an
- Su, Fangyi,Zhao, Zheng,Ma, Shuanggang,Wang, Rubing,Li, Yong,Liu, Yunbao,Li, Yuhuan,Li, Li,Qu, Jing,Yu, Shishan
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supporting information
p. 4920 - 4923
(2017/09/23)
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- Evaluation of Dual 5-Lipoxygenase/Microsomal Prostaglandin E2 Synthase-1 Inhibitory Effect of Natural and Synthetic Acronychia-Type Isoprenylated Acetophenones
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Among the pathways responsible for the development of inflammatory responses, the cyclooxygenase and lipoxygenase pathways are among the most important ones. Two key enzymes, namely, 5-LO and mPGES-1, are involved in the biosynthesis of leukotrienes and prostaglandins, respectively, which are considered attractive therapeutic targets, so their dual inhibition might be an effective strategy to control inflammatory deregulation. Several natural products have been identified as 5-LO inhibitors, with some also being dual 5-LO/mPGES-1 inhibitors. Here, some prenylated acetophenone dimers from Acronychia pedunculata have been identified for their dual inhibitory potency toward 5-LO and mPGES-1. To gain insight into the SAR of this family of natural products, the synthesis and biological evaluation of analogues are presented. The results show the ability of the natural and synthetic molecules to potently inhibit 5-LO and mPEGS-1 in vitro. The potency of the most active compound (10) has been evaluated in vivo in an acute inflammatory mouse model and displayed potent anti-inflammatory activity comparable in potency to the drug zileuton used as a positive control.
- Svouraki, Alexandra,Garscha, Ulrike,Kouloura, Eirini,Pace, Simona,Pergola, Carlo,Krauth, Verena,Rossi, Antonietta,Sautebin, Lidia,Halabalaki, Maria,Werz, Oliver,Gaboriaud-Kolar, Nicolas,Skaltsounis, Alexios-Leandros
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p. 699 - 706
(2017/04/01)
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- Synthesis, anti-phytopathogenic and DPPH radical scavenging activities of C-prenylated acetophenones and benzaldehydes
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The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These compounds were obtained by electrophilic aromatic substitution (SEAr) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl2 as a Lewis acid catalyst in ethyl acetate. Reasonable to good yields were obtained based on unrecovered aromatic starting material (45-73%). All the synthesized compounds were evaluated against phytopathogenic gram-negative bacteria Agrobacterium tumefaciens, Pseudomonas syringae and Erwinia carotovora and plant fungal pathogens Botrytis cinerea, Phytophthora cinnamomi and Gibberella fujikuroi. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay and expressed as half maximal inhibitory concentration (IC50) values in μM concentrations. The antioxidant activity went from 27.20 μM to >100 μM. Compound 11 showed statistically significant inhibition of the growth of Botrytis cinerea, and compounds 13 and 15 showed statistically significant inhibition of the growth of Phytophthora cinnamomi, with respect to negative control fungal growth. All six compounds showed bacteriostatic effects against gram-negative plant pathogenic bacteria with IC50 values between 250 and 3.9 μM.
- Osorio, Mauricio E.,Quiroz, Karol A.,Carvajal, Marcela A.,Vergara, Alejandra P.,Sánchez, Elizabeth Y.,González, Cesar E.,Catalán, Karen S.
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p. 3095 - 3101
(2016/11/17)
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- Total Synthesis and in Vitro Anti-Tumor-Promoting Activities of Racemic Acetophenone Monomers from Acronychia trifoliolata
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Six acetophenone derivatives, acronyculatins I (1), J (2), K (3), L (4), N (5), and O (6), were recently isolated from Acronychia trifoliolata, and the structure of the known acronyculatin B (7) was revised. Because of the limited quantities of isolated p
- Morita, Chihiro,Kobayashi, Yukiko,Saito, Yohei,Miyake, Katsunori,Tokuda, Harukuni,Suzuki, Nobutaka,Ichiishi, Eiichiro,Lee, Kuo-Hsiung,Nakagawa-Goto, Kyoko
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supporting information
p. 2890 - 2897
(2016/12/07)
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- Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds
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The phloroglucinol mallotojaponin C (1) from Mallotus oppositifolius, which was previously shown by us to have both antiplasmodial and cytocidal activities against the malaria parasite Plasmodium falciparum, was synthesized in three steps from 2′,4′,6′-tr
- Eaton, Alexander L.,Dalal, Seema,Cassera, M. Belen,Zhao, Shuqi,Kingston, David G. I.
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p. 1679 - 1683
(2016/07/06)
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- Towards the synthesis of platachromone b, a bioactive natural prenylated (E)-2-styrychromone
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Strategies towards the synthesis of the natural product platachromone B and related compounds have been investigated starting from commercially available phloroacetophenone. Direct C-prenylation of (E)-2-styryl-4H-chromen-4-ones was also studied. Methods
- Baptista, Frederico R.,Pinto, Diana C. G. A.,Silva, Artur M. S.
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p. 1116 - 1120
(2014/05/20)
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- Prenylflavonoids and prenyl/alkyl-phloroacetophenones: Synthesis and antitumour biological evaluation
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Several prenylflavonoids have been synthesised and tested against human tumour cell lines. The prenyl unit has been geranyl or a labdane diterpene. These labdane-flavonoids have been synthesised for the first time. The antitumour activity increase with the prenylation at C-8 position. Twenty-three C and O-prenylated acylphloroglucinols have been synthesised as well. In this case the C-alkylation products have resulted, in general, more active.
- Basabe,De Román,Marcos,Diez,Blanco,Bodero,Mollinedo,Sierra,Urones
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experimental part
p. 4258 - 4269
(2010/10/01)
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- Concise total synthesis of biologically interesting mallotophilippens C and E
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(Chemical Equation Presented) This paper describes a new and efficient synthetic approach for biologically interesting natural mallotophilippens C and E. The key strategies involved ethylenediamine diacetate-catalyzed benzopyran formation reactions and ba
- Yong, Rok Lee,Li, Xin,Jung, Hee Kim
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p. 4313 - 4316
(2008/09/20)
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- Identification of SVM-based classification model, synthesis and evaluation of prenylated flavonoids as vasorelaxant agents
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Support vector machine (SVM) was applied to predict vasorelaxation effect of different structural molecules. A good classification model had been established, and the accuracy in prediction for the training, test, and overall datasets was 93.0%, 82.6%, an
- Dong, Xiaowu,Liu, Yujie,Yan, Jingying,Jiang, Chaoyi,Chen, Jing,Liu, Tao,Hu, Yongzhou
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scheme or table
p. 8151 - 8160
(2009/04/11)
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- Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus
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The minor hop (Humulus lupulus) chalcones 3′-geranylchalconaringenin (3), 5′-prenylxanthohuraol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1″,2″-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3′-geranyl-6′-O- methylchalconaringenin (2), 3′-methylflavokawin (6), and 2′-0-methyl-3′-prenylchalconaringenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC 50 values comparable to xanthohumol (8.2-19.2 μM). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.
- Vogel, Susanne,Heilmann, Joerg
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scheme or table
p. 1237 - 1241
(2009/07/04)
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- Synthesis of four natural prenylflavonoids and their estrogen-like activities
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Four prenylflavonoids, bavachin 1, isobavachin 2, 7,4′-dihydroxy-8- prenylflavone 3, and 8-prenylapigenin 4 were synthesized and recognized for possessing estrogen-like activity in MCF-7/BOS cells, as evaluated by an estrogen-screening assay. All compound
- Dong, Xiaowu,Fan, Yongjian,Yu, Lingjun,Hu, Yongzhou
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p. 372 - 376
(2008/02/11)
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- The first prenylation step in hyperforin biosynthesis
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Prenylation reactions contribute considerably to the diversity of natural products. Polyprenylated secondary metabolites include hyperforin which is both quantitatively and pharmacologically a major constituent of the medicinal plant Hypericum perforatum
- Boubakir, Zakia,Beuerle, Till,Liu, Benye,Beerhues, Ludger
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- Anti-ulcer agent comprising chalcone derivative as effective ingredient and novel chalcone derivative
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The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: STR1 wherein X and Y independently stand for a hydrogen atom or together form a single bond, R1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R3 stands for hydroxyl group or a methoxy group, R4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R7 stands for a hydrogen atom or a methoxy group.
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- STRUCTURES OF CUDRAFLAVANONE A AND EUCHRESTAFLAVANONE C
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From the benzene extract of the root bark of Cudrania tricuspidata (Carr.) Bur. (Japanese name "Hariguwa", Moraceae), an isoprene substituted flavanone derivative, named cudraflavanone A, was isolated, for which structure (I) was determined on the basis o
- Fujimoto, Tomoko,Nomura, Taro
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p. 997 - 1003
(2007/10/02)
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