- Synthesis and acetylcholinesterase inhibitory activity of Mannich base derivatives flavokawain B
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A novel series of flavokawain B derivatives, chalcone Mannich bases (4-10) were designed, synthesized, characterized, and evaluated for the inhibition activity against acetylcholinesterase (AChE). Biological results revealed that four compounds displayed potent activities against AChE with IC50values below 20 μM. Moreover, the most promising compound 8 was 2-fold more active than rivastigmine, a well-known AChE inhibitor. The log P values of 4-10 were around 2 which indicated that they were sufficiently lipophilic to pass blood brain barriers in vivo. Enzyme kinetic study suggested that the inhibition mechanism of compound 8 was a mixed-type inhibition. Meanwhile, the molecular docking showed that this compound can both bind with the catalytic site and the periphery of AChE.
- Liu, Hao-Ran,Huang, Xue-Qin,Lou, Ding-Hui,Liu, Xian-Jun,Liu, Wu-Kun,Wang, Qiu-An
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- Chalcone methoxy derivatives exhibit antiproliferative and proapoptotic activity on canine lymphoma and leukemia cells
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Chalcones are interesting candidates for anti-cancer drugs due to the ease of their synthesis and their extensive biological activity. The study presents antitumor activity of newly synthesized chalcone analogues with a methoxy group on a panel of canine lymphoma and leukemia cell lines. The antiproliferative effect of the 20-hydroxychalcone and its methoxylated derivatives was evaluated in MTT assay after 48 h of treatment in different concentrations. The proapoptotic activity was studied by cytometric analysis of cells stained with Annexin V/FITC and propidium iodide and by measure caspases 3/7 and 8 activation. The DNA damage was evaluated by Western blot analysis of phosphorylated histone H2AX. The new compounds had selective antiproliferative activity against the studied cell lines, the most effective were the 20-hydroxy-200,500-dimethoxychalcone and 20-hydroxy-40,60-dimethoxychalcone. 20-Hydroxychalcone and the two most active derivatives induced apoptosis and caspases participation, but some percentage of necrotic cells was also observed. Comparing phosphatidylserine externalization after treatment with the different compounds it was noted that the addition of two methoxy groups increased the proapoptotic potential. The most active compounds triggered DNA damage even in the cell lines resistant to chalcone-induced apoptosis. The results confirmed that the analogues could have anticancer potential in the treatment of canine lymphoma or leukemia.
- ?uz?ny, Mateusz,Henklewska, Marta,Janeczko, Tomasz,Koz?owska, Ewa,Obmińska-Mrukowicz, Bozena,Pawlak, Aleksandra,Suárez, Beatriz Hernández
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- An efficient synthesis of chrysin
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Two routes for the synthesis of the flavones chrysin are described. In the first 1,3,5-trimethoxybenzene was converted to 2-hydroxy-4,6- dimethoxyacetophenone and then by condensation with benzaldehyde to 2′-hydroxy-4′,6′-dimethoxychalcone. The latter was cyclised with iodine and demethylated with pyridine hydrochloride to form chrysin in 53% overall yield. In the second route, 1,3,5-trimethoxybenzene was acylated with cinnamic acid to form the chalcone which was then converted to chrysin in 30.7% overall yield.
- Liu, Man,Zhang, Ji,Yang, Jian,Yang, Bo,Cui, Wei
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- Development of a concise synthesis of the flavonoid chrysin
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Two novel routes for the synthesis of the flavonoid chrysin are described. In the first, 3,5-dimethoxyphenol (taxicatigenin) was converted to 2-hydroxy-4,6-dimethoxyacetophenone and then by condensation with benzaldehyde to 2'-hydroxy-4',6'-dimethoxychalcone. The latter was cyclised with iodine and demethylated with pyridine hydrochloride to form chrysin in 50% overall yield. In the second route, taxicatigenin was acylated with cinnamoyl chloride to form a chalcone under special conditions. This was then converted to chrysin in 42% and 56% overall yield, respectively. Several disadvantages of previous syntheses like long reaction time, tedious work-up and low overall yield have been overcome.
- Wang, Qian,Cui, Wei,Yang, Jian,Yang, Bo
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- Melanogenic inhibition and toxicity assessment of flavokawain A and B on B16/F10 melanoma cells and zebrafish (Danio rerio)
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Excessive production of melanin implicates hyperpigmentation disorders. Flavokawain A (FLA) and flavokawain B (FLB) have been reported with anti-melanogenic activity, but their melanogenic inhibition and toxicity effects on the vertebrate model of zebrafish are still unknown. In the present study, cytotoxic as well as melanogenic effects of FLA and FLB on cellular melanin content and tyrosinase activity were evaluated in α-MSH-induced B16/F10 cells. Master regulator of microphthalmia-associated transcription factor (Mitf) and the other downstream melanogenic-related genes were verified via quantitative real time PCR (qPCR). Toxicity assessment and melanogenesis inhibition on zebrafish model was further observed. FLA and FLB significantly reduced the specific cellular melanin content by 4.3-fold and 9.6-fold decrement, respectively in α-MSH-induced B16/F10 cells. Concomitantly, FLA significantly reduced the specific cellular tyrosinase activity by 7-fold whilst FLB by 9-fold. The decrement of melanin production and tyrosinase activity were correlated with the mRNA suppression of Mitf which in turn down-regulate Tyr, Trp-1 and Trp-2. FLA and FLB exhibited non-toxic effects on the zebrafish model at 25 and 6.25 μM, respectively. Further experiments on the zebrafish model demonstrated successful phenotype-based depigmenting activity of FLA and FLB under induced melanogenesis. To sum up, our findings provide an important first key step for both of the chalcone derivatives to be further studied and developed as potent depigmenting agents.
- Abdul Bahari, Mohammad Nazri,Ahmad, Syahida,Akhtar, Muhammad Nadeem,Balia Yusof, Zetty Norhana,Latif, Naimah,Md Razip, Nurliyana Najwa,Mohd Ma’in, Farah Idayu,Sakeh, Nurshafika Mohd
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- A novel one-pot synthesis of flavones
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In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.
- Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi
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p. 11655 - 11662
(2021/03/31)
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- Biotransformation of 5,7-Methoxyflavones by Selected Entomopathogenic Filamentous Fungi
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5,7-Dimethoxyflavone, a chrysin derivative, occurs in many plants and shows very low toxicity, even at high doses. On the basis of this phenomenon, we biotransformed a series of methoxy-derivatives of chrysin, apigenin, and tricetin obtained by chemical synthesis. We used entomopathogenic fungal strains with the confirmed ability of simultaneous hydroxylation/demethylation and glycosylation of flavonoid compounds. Both the amount and the place of attachment of the methoxy group influenced the biotransformation rate and the product's amount nascent. Based on product and semi-product structures, it can be concluded that they are the result of cascading transformations. Only in the case of 5,7,3′,4′,5′-pentamethoxyflavone, the strains were able to attach a sugar molecule in place of the methoxy substituent to give 3′-O-β-d-(4″-O-methylglucopyranosyl)-5,7,4′,5′-tetramethoxyflavone. However, we observed the tested strains' ability to selectively demethylate/hydroxylate the carbon C-3′ and C-4′ of ring B of the substrates used. The structures of four hydroxyl-derivatives were determined: 4′-hydroxy-5,7-dimethoxyflavone, 3′-hydroxy-5,7-dimethoxyflavone, 3′-hydroxy-5,7,4′,5′-tetramethoxyflavone, and 5,7-dimethoxy-3′,4′-dihydroxyflavone (5,7-dimethoxy-luteolin).
- ?u?ny, Mateusz,Tronina, Tomasz,Koz?owska, Ewa,Kostrzewa-Sus?ow, Edyta,Janeczko, Tomasz
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p. 3879 - 3886
(2021/05/04)
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- Discovery of polymethoxyflavones as potential cyclooxygenase-2 (COX-2), 5-lipoxygenase (5-LOX) and phosphodiesterase 4B (PDE4B) inhibitors
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Non-steroidal anti-inflammatory drugs (NSAIDs) are widely prescribed to treat inflammatory-related diseases, pain and fever. However, the prolong use of traditional NSAIDs leads to undesirable side effects such as gastric, ulceration, and renal toxicity due to lack of selectivity toward respective targets for COX-2, 5-LOX, and PDE4B. Thus, targeting multiple sites can reduce these adverse effects of the drugs and increase its potency. A series of methoxyflavones (F1–F5) were synthesized and investigated for their anti-inflammatory properties through molecular docking and inhibition assays. Among these flavones, only F2 exhibited selectivity toward COX-2 (Selectivity Index, SI: 3.90, COX-2 inhibition: 98.96 ± 1.47%) in comparison with celecoxib (SI: 7.54, COX-2 inhibition: 98.20 ± 2.55%). For PDEs, F3 possessed better selectivity to PDE4B (SI: 4.67) than rolipram (SI: 0.78). F5 had the best 5-LOX inhibitory activity among the flavones (33.65 ± 4.74%) but less than zileuton (90.81 ± 0.19%). Docking analysis indicated that the position of methoxy group and the substitution of halogen play role in determining the bioactivities of flavones. Interestingly, F1–F5 displayed favorable pharmacokinetic profiles and acceptable range of toxicity (IC50>70 μM) in cell lines with the exception for F1 (IC50: 16.02 ± 1.165 μM). This study generated valuable insight in designing new anti-inflammatory drug based on flavone scaffold. The newly synthesized flavones can be further developed as future therapeutic agents against inflammation.
- Hamzah, Ahmad Sazali,Md Idris, Muhd Hanis,Mohd Amin, Siti Norhidayah,Mohd Amin, Siti Norhidayu,Salleh, Mohd Zaki,Selvaraj, Manikandan,Shaameri, Zurina,Teh, Lay Kek,Wibowo, Agustono,Zakaria, Zainul Amiruddin
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- Chalcone derivative and application thereof
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The invention discloses a chalcone derivative and application thereof. The chemical structure of the chalcone derivative is shown as a formula (a) or a formula (b). The chalcone derivative can effectively inhibit proliferation of tumor cells, and a novel lead compound is provided for development of antitumor drugs.
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Paragraph 0014-0016
(2021/07/01)
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- Development of a novel nitric oxide (NO) production inhibitor with potential therapeutic effect on chronic inflammation
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Inflammation is a complex biological response to stimuli. Activated macrophages induced excessively release of pro-inflammatory cytokines and mediators such as endogenous radical nitric oxide (NO) play a significant role in the progression of multiple inflammatory diseases. Both natural and synthetic chalcones possess a wide range of bioactivities. In this work, thirty-nine chalcones and three related compounds, including several novel ones, based on bioactive kava chalcones were designed, synthesized and their inhibitory effects on NO production in RAW 264.7 cells were evaluated. The novel compound (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3-methoxy-4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one (53) exhibited a better inhibitory activity (84.0%) on NO production at 10 μM (IC50 = 6.4 μM) with the lowest cytotoxicity (IC50 > 80 μM) among the tested compounds. Besides, western blot analysis indicated that compound 53 was a potent down-regulator of inducible nitric oxide synthase (iNOS) protein. Docking study revealed that compound 53 also can dock into the active site of iNOS. Furthermore, at the dose of 10 mg/kg/day, compound 53 could both significantly suppress the progression of inflammation on collagen-induced arthritis (CIA) and adjuvant-induced arthritis (AIA) models. In addition, the structure-activity relationship (SAR) of the kava chalcones based analogs was also depicted.
- Chen, Lijuan,Fan, Tiantian,Lei, Xiangui,Teichmann, Alexander Tobias,Wang, Amu,Wang, Chao,Wei, Zhe,Wieland, Frank Heinrich,Yang, Youzhe,Yin, Jinxiang,Zhou, Li,Zhu, Yue
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- Design, synthesis and biological evaluation of dimethyl cardamonin (DMC) derivatives as P-glycoprotein-mediated multidrug resistance reversal agents
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Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting P-gp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin (DMC). Subsequently, we evaluated their reversal activities as potential P-glycoprotein (P-gp)-mediated Multidrug Resistance (MDR) agents. Methods: Dimethyl cardamonin derivatives were synthesized from acetophenones and the corresponding benzaldehydes in the presence of 40% KOH by Claisen-Schmidt reaction. Their cytotoxicity and reversal activities in vitro were assessed with MTT. Moreover, the compound B4 was evaluated by Doxorubicin (DOX) accumulation, Western blot and wound-healing assays deeply. Results and Discussion: The results showed that compounds B2, B4 and B6 had the potency of MDR reversers with little intrinsic cytotoxicity. Meanwhile, these compounds also demonstrated the capability to inhibit MCF-7 and MCF-7/DOX cells migration. Besides, the most compound B4 was selected for further study, which promoted the accumulation of DOX in MCF-7/DOX cells and inhibited the expressionof P-gp at protein levels. Conclusion: The above findings may provide new insights for the research and development of P-gp-mediated MDR reversal agents.
- Liu, Jianwen,Ma, Lei,Shi, Ximeng,Yin, Huanhuan,Zhao, Yuyu,Zhou, Licheng
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p. 1270 - 1282
(2020/10/06)
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- Chalcone analogue and application thereof
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The invention discloses a chalcone analogue and application thereof, wherein the structure of the chalcone analogue is shown as a formula (I), and R is selected from substituted or unsubstituted arylor heteroaryl; the substituent groups on the aryl group
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Paragraph 0034-0040; 0051-0052
(2020/07/02)
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- Novel chromenone derivatives having substituted biphenyl group and a pharmaceutical composition for prevention or treatment of allergic diseases compring the same
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The present invention relates to: a novel chromenone derivative compound capable of effectively suppressing an allergic immune response by inhibiting signal transduction mediated by thymic stromal lymphopoietin (TSLP); and a pharmaceutical composition capable of fundamentally preventing or treating various allergic diseases by using the same.COPYRIGHT KIPO 2021
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Paragraph 0076-0083
(2020/11/26)
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- Attrition-enhanced deracemization and absolute asymmetric synthesis of flavanones from prochiral precursors
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Seven racemic 5,7-dimethoxyflavanones afforded conglomerate crystals upon recrystallization from a solvent. Three methodologies were investigated to achieve asymmetric transformation based on dynamic crystallization of the chiral conglomerate system. The first was chiral symmetry breaking of racemic flavanones by attrition-enhanced deracemization. Continuous suspension of racemic flavanones in a small amount of propanol in the presence of a base (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) and glass beads promoted chiral symmetry breaking and converted the flavanones to crystals of (+)- or (-)-enantiomers with 78 to 99% ee. The second method involved cyclization of the intermediate aldol product to give optically active flavanone with 90% ee involving a reversible oxa-Michael addition reaction with attrition-enhanced deracemization. The third was a reaction starting from prochiral 2-hydroxy-4,6-dimethoxyacetophenone and 2-naphthaldehyde under basic conditions, which gave the corresponding flavanone in 89% ee.
- Kasashima, Yoshio,Mino, Takashi,Sakamoto, Masami,Shimizu, Waku,Uemura, Naohiro,Yoshida, Yasushi
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p. 5676 - 5681
(2020/10/13)
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- Enzyme-assisted cyclization of chalcones to flavanones
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Enzyme catalyzed synthesis is an eco-friendly technique in organic synthesis, having several benefits over conventional methods. In the present work, we describe a simple process of laccase and chloroperoxidase assisted cyclization of chalcones, leading to the formation of flavanones. The reaction proceeds in a mixture of phosphate buffer and ethanol, under oxygen atmosphere at room temperature, yielding the corresponding flavanone in good to moderate yield. The relative configuration of the products at C2 is tentatively assigned as S*-flavanone based on the coupling constants with the methylenic protons H3α,β. In comparison to the chemical methods, we describe a process which can be achieved efficiently under mild conditions using oxygen as oxidant.
- Alonso, Mariana Macías,Boluda, Carlos José,Barajas, Gabriela Díaz,Sánchez, Nallely Caldera,Córdova-Guerrero, Iván,Marrero, Joaquín González
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p. 926 - 931
(2020/12/23)
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- The winding road of the uvaretin class of natural products: From total synthesis to bioactive agent discovery
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Herein, we disclose the development of a synthetic route to gain access to the uvaretin class of chalcone natural products. In this, the construction of a small library was achieved, and the collection was evaluated for cytotoxicity and other biological properties. Uvaretin (1) was accessed via a seven-step route in an overall yield of 15.1%. Within this route, the unsaturated enone variant of uvaretin (2), also a natural product, was accessed in a 16.7% yield over six steps. This route provides a nearly three-fold increase in yields of 1 and 2 in comparison to the previous synthetic route accessing them in 5.8% and 3.0% overall yields, respectively. Evaluation of 1 and 2 revealed IC50 values between 2.0 and 5.1 μM in the cancerous cell lines HeLa, U937, A549, and MIA PaCa-2. Screening of the whole chalcone library set led to the discovery of over 30 compounds, within six cancerous cell lines, possessing single digit μM IC50 activity as sole agents. Furthermore, multiple library members were found to possess promising potentiating properties with known chemotherapeutic agents.
- Dallman, Johnathan,Lansakara, Ashabha,Nguyen, Thi,Weeramange, Chamitha,Hulangamuwa, Wasundara,Rafferty, Ryan J.
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p. 1420 - 1431
(2019/08/21)
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- Synthesis of Benzopyran-Fused Flavone Derivatives via Microwave-Assisted Intramolecular C-H Activation
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A microwave-assisted intramolecular direct arylation method for the synthesis of benzopyran-fused flavone derivatives containing natural flavone backbones is described. Different polyalkoxy flavones were synthesized and functionalized with 2-bromobenzyl bromide. The resulting compounds were subjected to palladium-catalyzed intramolecular direct arylation reactions supported by microwave irradiation to produce fused tetracyclic flavones. In the case of the 7-substituted chrysin derivative, the regioselectivity of the coupling was also examined.
- Sipos, Zoltán,Kónya, Krisztina
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p. 1610 - 1620
(2018/03/21)
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- In Vitro and in Vivo Antischistosomal Activities of Chalcones
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In this study, we evaluated the in vitro and in vivo schistosomicidal activities of chalcones against Schistosoma mansoni worms. In vitro assays revealed that chalcones 1 and 3 were the most active compounds, without affecting significantly mammalian cells. Confocal laser scanning microscopy and scanning electron microscopy studies revealed reduction on the numbers of tubercles and morphological alterations in the tegument of S. mansoni worms after in vitro incubation with chalcones 1 and 3. In a mouse model of schistosomiasis, the oral treatment (400 mg/kg) with chalcone 1 or 3 significantly caused a total worm burden reduction in mice. Chalcone 1 showed significant inhibition of the S. mansoni ATP diphosphohydrolase activity, which was corroborated by molecular docking studies. The results suggested that chalcones could be explored as lead compounds with antischistosomal properties.
- Pereira, Vinícius R. D.,Junior, Ismael J. Alves,da Silveira, Lígia S.,Geraldo, Reinaldo B.,de F. Pinto, Priscila,Teixeira, Fernanda S.,Salvadori, Maria C.,Silva, Marcos P.,Alves, Lara A.,Capriles, Priscila V. S. Z.,das C. Almeida, Ayla,Coimbra, Elaine S.,Pinto, Pedro L. S.,Couri, Mara R. C.,de Moraes, Josué,Da Silva Filho, Ademar A.
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- Design, synthesis and docking studies of flavokawain B type chalcones and their cytotoxic effects on MCF-7 and MDA-MB-231 cell lines
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Flavokawain B (1) is a natural chalcone extracted from the roots of Piper methysticum, and has been proven to be a potential cytotoxic compound. Using the partial structure of flavokawain B (FKB), about 23 analogs have been synthesized. Among them, compounds 8, 13 and 23 were found in new FKB derivatives. All compounds were evaluated for their cytotoxic properties against two breast cancer cell lines, MCF-7 and MDA-MB-231, thus establishing the structure-activity relationship. The FKB derivatives 16 (IC50 = 6.50 ± 0.40 and 4.12 ± 0.20 μg/mL), 15 (IC50 = 5.50 ± 0.35 and 6.50 ± 1.40 μg/mL) and 13 (IC50 = 7.12 ± 0.80 and 4.04 ± 0.30 μg/mL) exhibited potential cytotoxic effects on the MCF-7 and MDA-MB-231 cell lines. However, the methoxy group substituted in position three and four in compound 2 (IC50 = 8.90 ± 0.60 and 6.80 ± 0.35 μg/mL) and 22 (IC50 = 8.80 ± 0.35 and 14.16 ± 1.10 μg/mL) exhibited good cytotoxicity. The lead compound FKB (1) showed potential cytotoxicity (IC50 = 7.70 ± 0.30 and 5.90 ± 0.30 μg/mL) against two proposed breast cancer cell lines. It is evident that the FKB skeleton is unique for anticancer agents, additionally, the presence of halogens (Cl and F) in position 2 and 3 also improved the cytotoxicity in FKB series. These findings could help to improve the future drug discovery process to treat breast cancer. A molecular dynamics study of active compounds revealed stable interactions within the active site of Janus kinase. The structures of all compounds were determined by 1H-NMR, EI-MS, IR and UV and X-ray crystallographic spectroscopy techniques.
- Bakar, Addila Abu,Akhtar, Muhammad Nadeem,Ali, Norlaily Mohd,Yeap, Swee Keong,Quah, Ching Kheng,Loh, Wan-Sin,Alitheen, Noorjahan Banu,Zareen, Seema,Ul-Haq, Zaheer,Shah, Syed Adnan Ali
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- In Vitro Osteogenic Differentiation and Antibacterial Potentials of Chalcone Derivatives
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Chalcone derivatives have been investigated as therapeutic agents for the anticancer, antioxidant, and anti-inflammatory fields. In this study, we have synthesized four different types of chalcone derivatives and demonstrated in vitro bioactivities. We divided these derivatives into two groups of chalcones on the basis of similar substituents on the aromatic rings, and we tested cell viability and proliferation potentials, which indicated that the methoxy substituent on the A ring could enhance cytotoxicity and antiproliferation potential depending on the chalcone concentration. We also investigated osteogenic differentiation of C2C12 cells by ALP staining, the early marker for osteogenesis, which demonstrated that the chalcones could not only induce activity of BMP-2 but also inhibit the activity of noggin, a BMP antagonist. In addition, chalcone bearing hydroxyl groups at the 2-, 4-, and 6-position on the A ring inhibited treptococcus mutans growth, a major causative agent of dental caries. Therefore, we concluded that the chalcone derivatives synthesized in this research can be good candidates for therapeutic agents promoting bone differentiation, with an expectation of inhibiting S. mutans, in dentistry.
- Choi, Daheui,Park, Jin Chan,Lee, Ha Na,Moon, Ji-Hoi,Ahn, Hyo-Won,Park, Kwangyong,Hong, Jinkee
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p. 3197 - 3204
(2018/07/25)
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- Chalcone derivatives enhance ATP-binding cassette transporters A1 in human THP-1 macrophages
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Atherosclerosis is a process of imbalanced lipid metabolism in the vascular walls. The underlying pathology mainly involves the deposition of oxidized lipids in the endothelium and the accumulation of cholesterol in macrophages. Macrophages export excessive cholesterol (cholesterol efflux) through ATP-binding cassette transporter A1 (ABCA1) to counter the progression of atherosclerosis. We synthesized novel chalcone derivatives and assessed their effects and the underlying mechanisms on ABCA1 expression in macrophages. Human THP-1 macrophages were treated with synthetic chalcone derivatives for 24 h. In Western blot and flow cytometry analyses, a chalcone derivative, (E)-1-(3,4-diisopropoxyphenyl)-3-(4-isopropoxy-3-methoxyphenyl)prop- 2-en-1-one (1m), was observed to significantly enhance ABCA1 protein expression in THP-1 cells (10 μM, 24 h). Levels of mRNA of ABCA1 and liver X receptor alpha (LXRα) were quantified using a real-time quantitative polymerase chain reaction technique and were found to be significantly increased after treatment with the novel chalcone derivative 1m. Several microRNAs, including miR155, miR758, miR10b, miR145, miR33, and miR106b, which functionally inhibit ABCA1 expression were suppressed after treatment with 1m. Collectively, 1m increases ABCA1 expression in human THP-1 macrophages. The mechanisms involve the activation of the LXRα-ABCA1 pathway and suppression of certain microRNAs that regulate ABCA1 expression.
- Teng, I-Jou,Tsai, Min-Chien,Shih, Shao-Fu,Tsuei, Bi-Feng,Chang, Hsin,Chuang, Yi-Ping,Lin, Chin-Sheng,Chern, Ching-Yuh,Chen, Sy-Jou
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- Unveiling the 6,8-Rearrangement in 8-Phenyl-5,7-dihydroxyflavylium and 8-Methyl-5,7-dihydroxyflavylium through Host–Guest Complexation
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8-Phenyl-5,7-dihydroxyflavylium and 8-methyl-5,7-dihydroxyflavylium were synthesized to observe the 6,8-rearrangement. 8-Phenyl and 8-methyl residues were introduced by Suzuki–Miyaura reaction of 8-iodochrysin, then reduced by LiAlH4 to give the corresponding 3-deoxyanthocyanidins. At pH 1.0 the stable form is the 8-substituted flavylium cation in both compounds. At higher pH values the quinoidal bases are the stable species and some evidence for the 6,8-rearrangement was obtained, but the respective spectral variations are very small. This was overcome by using a modified cyclodextrin (captisol), which favors the formation of the trans-chalcone at the expense of the quinoidal bases. The trans-chalcone was isolated and dissolved in CD3OD/DCl (pD + m/z 253). The 6-isomer slowly reverts to the most stable 8-isomer. The 6,8-rearrangement was also observed after irradiation of the trans-chalcone (in the presence of captisol) at pH 5. Acidification of this photostationary state gave a mixture of both flavylium cations. The UV/Vis absorption of the flavylium cation (6-isomer) was blueshifted in comparison to the 8-isomer.
- Basílio, Nuno,Lima, Jo?o Carlos,Cruz, Luís,de Freitas, Victor,Pina, Fernando,Ando, Hiroki,Kimura, Yuki,Oyama, Kin-Ichi,Yoshida, Kumi
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p. 5617 - 5626
(2017/10/13)
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- Mechanisms of action and structure-activity relationships of cytotoxic flavokawain derivatives
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22 Flavokawain derivatives (FKd) were obtained by one step syntheses in order to conduct a SAR study to understand the structural requirements for optimum and selective cytotoxicity. FKd and natural flavokawains A and B found into kava, a South Pacific traditional beverage, were evaluated against nine cancer and one healthy cell lines. The targeted cell cycle phases as well as the effects on the induction of apoptosis and cell cycle protein levels were investigated. Therapeutic improvements (more activity and selectivity) were achieved with FKd compared to natural flavokawains and notably with the 2′,3,4′,6′-tetramethoxychalcone (FKd 19). FKd induced a G1/S arrest on p53 wild-type cells and an M arrest on p53 mutant-type, via the up-regulation of p21 and cyclin B1 proteins, followed by apoptosis. Moreover, FKd exhibited a 24?h-effect on Akt/mTor normal cells versus a 48?h-effect on Akt/mTor up-regulated cells. The SAR study resulted in the conclusion that trimethoxy A-ring allowed the best compromise between cytotoxicity and selectivity, as well as the substitution of the meta position on the B-ring and the use of halogens substituents.
- Thieury, Charlotte,Lebouvier, Nicolas,Le Guével, Rémy,Barguil, Yann,Herbette, Ga?tan,Antheaume, Cyril,Hnawia, Edouard,Asakawa, Yoshinori,Nour, Mohammed,Guillaudeux, Thierry
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p. 1817 - 1829
(2017/03/08)
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- 2-substituted benzopyran-4-one compounds and application thereof
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The invention relates to the technical field of medicine and discloses 2-substituted benzopyran-4-one compounds with a structure shown in general formula I and an application of the compounds in preparation of antifungal drugs and synergistic antifungal drugs. The compounds can be jointly used with azole antifungal drugs, can improve sensibility of drug-resistance bacteria to the azole drugs, reverses drug resistance and produces a synergistic antifungal function.
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Paragraph 0173
(2016/10/08)
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- Design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship
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Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1-10) have been synthesized and examined for their tryrosinase inhibitory activity. The results showed that flavokawain B (1), flavokawain A (2) and compound 3 were found to be potential tyrosinase inhibitors, indicating IC50 14.20-14.38 μM values. This demonstrates that 4-substituted phenolic compound especially at ring A exhibited significant tyrosinase inhibition. Additionally, molecular docking results showed a strong binding affinity for compounds 1-3 through chelation between copper metal and ligands. The detailed molecular docking and SARs studies correlate well with the tyrosinase inhibition studies in vitro. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and single X-ray crystallographic techniques. These findings could lead to design and discover of new tyrosinase inhibitors to control the melanine overproduction and overcome the economic loss of food industry.
- Akhtar, Muhammad Nadeem,Sakeh, Nurshafika M.,Zareen, Seema,Gul, Sana,Lo, Kong Mun,Ul-Haq, Zaheer,Shah, Syed Adnan Ali,Ahmad, Syahida
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- Flavokawains B and C, melanogenesis inhibitors, isolated from the root of Piper methysticum and synthesis of analogs
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The ethanolic extract of the root of Piper methysticum was found to inhibit melanogenesis in MSH-activated B16 melanoma cells. Flavokawains B and C were isolated from this extract based on their anti-melanogenesis activity and found to inhibit melanogenesis with IC50 values of 7.7 μM and 6.9 μM, respectively. Flavokawain analogs were synthesized through a Claisen-Schmidt condensation of their corresponding acetophenones and benzaldehydes and were evaluated in terms of their tyrosinase inhibitory and anti-melanogenesis activities. Compound 1b was the most potent of these with an IC50 value of 2.3 μM in melanogenesis inhibition assays using MSH-activated B16 melanoma cells.
- Jeong, Hye-Jin,Lee, Chang Seok,Choi, Janggyoo,Hong, Yong Deog,Shin, Song Seok,Park, Jun Seong,Lee, John Hwan,Lee, Seokyong,Yoon, Kee Dong,Ko, Jaeyoung
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p. 799 - 802
(2015/02/19)
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- Pro-angiogenic effects of chalcone derivatives in zebrafish embryos in vivo
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The aim of this study was to investigate novel chalcones with potent angiogenic activities in vivo. Chalcone-based derivatives were evaluated using a transgenic zebrafish line with fluorescent vessels to real-time monitor the effect on angiogenesis. Results showed that the chalcone analogues did not possess anti-angiogenic effect on zebrafish vasculatures; instead, some of them displayed potent pro-angiogenic effects on the formation of the sub-intestinal vein. Similar pro-angiogenic effects can also be seen on wild type zebrafish embryos. Moreover, the expression of vegfa, the major regulator for angiogenesis, was also upregulated in their treatment. Taken together, we have synthesized and identified a series of novel chalcone-based derivatives as potent in vivo pro-angiogenic compounds. These novel compounds hold potential for therapeutic angiogenesis.
- Chen, Yau-Hung,Chang, Chao-Yuan,Chang, Chiung-Fang,Chen, Po-Chih,Lee, Ya-Ting,Chern, Ching-Yuh,Tsai, Jen-Ning
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p. 12512 - 12524
(2015/08/06)
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- Flavokawain derivative or pharmaceutically acceptable salt thereof having inhibitory activity on Hsp90 and medical use thereof
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The present invention relates to a flavokawain derivative or a pharmaceutically acceptable salt thereof having an activity for inhibiting Hsp90 and a medical use thereof wherein the flavokawain derivative comprises good effect of inhibiting Hsp90 and accordingly leads to decomposition of Hsp 90 client protein causing diseases related to cancer or neurodegenerative diseases by inhibiting Hsp90, thereby being used in drug medicine and healthy food products for preventing or treating Hsp 90 which is a mediated disease like diseases related to cancer or neurodegenerative diseases.COPYRIGHT KIPO 2015
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Paragraph 0073-0077
(2016/10/10)
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- Synthesis of flavokawain analogues and their anti-neoplastic effects on drug-resistant cancer cells through Hsp90 inhibition
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Hsp90 is an ubiquitous molecular chaperone protein, which plays an important role in regulating maturation and stabilization of many oncogenic proteins. Due to its potential to simultaneously disable multiple signaling pathways, Hsp90 represents great promise as a therapeutic target of cancer. In this study, we synthesized flavokawain analogues and evaluated their biological activities against drug-resistant cancer cells. The study indicated that compound 1i impaired the growth of gefitinib-resistant non-small cell lung cancer (H1975), down-regulated the expression of Hsp90 client proteins including EGFR, Her2, Met, Akt and Cdk4, and upregulated the expression of Hsp70. The result strongly suggested that compound 1i inhibited the proliferation of cancer cells through Hsp90 inhibition. Overall, compound 1i could serve as a potential lead compound to overcome the drug resistance in cancer chemotherapy.
- Seo, Young Ho,Park, Sun You
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p. 1154 - 1158
(2014/05/06)
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- Aurones as histone deacetylase inhibitors: Identification of key features
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In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET-based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 μM in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation.
- Zwick, Vincent,Chatzivasileiou, Alkiviadis-Orfefs,Deschamps, Nathalie,Roussaki, Marina,Simes-Pires, Claudia A.,Nurisso, Alessandra,Denis, Iza,Blanquart, Christophe,Martinet, Nadine,Carrupt, Pierre-Alain,Detsi, Anastasia,Cuendet, Muriel
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supporting information
p. 5497 - 5501
(2014/12/12)
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- Intermolecular C-O addition of carboxylic acids to arynes: Synthesis of o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones
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An efficient and simple route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed utilizing readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl tr
- Dubrovskiy, Anton V.,Larock, Richard C.
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p. 2789 - 2798
(2013/03/29)
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- Synthesis of flavokawain B and its anti-Proliferative activity against gefitinib-Resistant non-Small cell lung cancer (NSCLC)
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Non-small cell lung cancer (NSCLC) is the most common type of lung cancer and that accounts for 85% of lung cancer patients. Although several EGFR-targeted drugs have been developed in the treatment of NSCLC, the clinical efficacy of EGFR-targeted drugs in NSCLC is limited by the occurrence of drug resistance. In this regard, Hsp90 represents great promise as a therapeutic target of cancer due to its potential to simultaneously disable multiple signaling pathways. In this study, we discovered that a natural product, flavokawain B disrupted Hsp90 chaperoning function and impaired the growth of gefitinib-resistant non-small cell lung cancer (H1975). The result suggested that flavokawain B could serve as a potential lead compound to overcome the drug resistance in cancer chemotherapy.
- Seo, Young Ho,Oh, Yong Jin
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p. 3782 - 3786
(2014/01/17)
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- Synthesis, structure-activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors
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In a continuing study for discovering urease inhibitors based on flavonoids, nineteen reductive derivatives of flavonoids were synthesized and evaluated against Helicobacter pylori urease. Analysis of structure-activity relationship disclosed that 4-deoxy analogues are more potent than other reductive products. Out of them, 4′,7,8-trihydroxyl-2-isoflavene (13) was found to be the most active with IC50 of 0.85 μM, being over 20-fold more potent than the commercial available urease inhibitor, acetohydroxamic acid (AHA). Kinetics study revealed that 13 is a competitive inhibitor of H. pylori urease with a Ki value of 0.641 μM, which is well matched with the results of molecular docking. Biological evaluation and mechanism study of 13 suggest that it is a good candidate for discovering novel anti-gastritis and anti-gastric ulcer agent.
- Xiao, Zhu-Ping,Peng, Zhi-Yun,Dong, Jing-Jun,He, Juan,Ouyang, Hui,Feng, Yu-Ting,Lu, Chun-Lei,Lin, Wan-Qiang,Wang, Jin-Xiang,Xiang, Yin-Ping,Zhu, Hai-Liang
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p. 685 - 695
(2013/07/25)
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- In vitro inhibitory properties of ferrocene-substituted chalcones and aurones on bacterial and human cell cultures
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Two series of ten chalcones and ten aurones, where ferrocene replaces the C ring and with diverse substituents on the A ring were synthesized. The compounds were tested against two antibiotic-sensitive bacterial strains, E. coli ATCC 25922 and S. aureus ATCC 25923, and two antibiotic-resistant strains, S. aureus SA-1199B and S. epidermidis IPF896. The unsubstituted compound and those with methoxy substitution showed an inhibitory effect on all bacterial strains at minimum inhibitory concentrations ranging between 2 and 32 mg L -1. For four of these compounds, the effect was bactericidal, as opposed to bacteriostatic. The corresponding organic aurones did not show growth inhibition, underscoring the role of the ferrocene group. The methoxy-substituted aurones and the unsubstituted aurone also showed low micromolar (IC50) activity against MRC-5 non-tumoral lung cells and MDA-MB-231 breast cancer cells, suggesting non-specific toxicity.
- Tiwari, Keshri Nath,Monserrat, Jean-Philippe,Hequet, Arnaud,Ganem-Elbaz, Carine,Cresteil, Thierry,Jaouen, Gerard,Vessieres, Anne,Hillard, Elizabeth A.,Jolivalt, Claude
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experimental part
p. 6451 - 6457
(2012/09/21)
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- A synthetic chalcone as a potent inducer of glutathione biosynthesis
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Chalcones continue to attract considerable interest due to their anti-inflammatory and antiangiogenic properties. We recently reported the ability of 2′,5′-dihydroxychalcone (2′,5′-DHC) to induce both breast cancer resistance protein-mediated export of glutathione (GSH) and c-Jun N-terminal kinase-mediated increased intracellular GSH levels. Herein, we report a structure-activity relationship study of a series of 30 synthetic chalcone derivatives with hydroxyl, methoxyl, and halogen (F and Cl) substituents and their ability to increase intracellular GSH levels. This effect was drastically improved with one or two electrowithdrawing groups on phenyl ring B and up to three methoxyl and/or hydroxyl groups on phenyl ring A. The optimal structure, 2-chloro-4′,6′-dimethoxy-2′- hydroxychalcone, induced both a potent NF-E2-related factor 2-mediated transcriptional response and an increased formation of glutamate cysteine ligase holoenzyme, as shown using a human breast cancer cell line stably expressing a luciferase reporter gene driven by antioxidant response elements.
- Kachadourian, Remy,Day, Brian J.,Pugazhenti, Subbiah,Franklin, Christopher C.,Genoux-Bastide, Estelle,Mahaffey, Gregory,Gauthier, Charlotte,Di Pietro, Attilio,Boumendjel, Ahcène
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experimental part
p. 1382 - 1388
(2012/04/04)
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- Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: Critical role of methoxylation in both inhibition potency and cytotoxicity
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ABCG2 plays a major role in anticancer-drug efflux and related tumor multidrug resistance. Potent and selective ABCG2 inhibitors with low cytotoxicity were investigated among a series of 44 chalcones and analogues (1,3-diarylpropenones), by evaluating their inhibitory effect on the transport of mitoxantrone, a known ABCG2 substrate. Six compounds producing complete inhibition with IC50 values below 0.5 μM and high selectivity for ABCG2 were identified. The number and position of methoxy substituents appeared to be critical for both inhibition and cytotoxicity. The best compounds, with potent inhibition and low toxicity, contained an N-methyl-1-indolyl (compound 38) or a 6′-hydroxyl-2′,4′-dimethoxy-1-phenyl (compound 27) moiety (A-ring) and two methoxy groups at positions 2 and 6 of the 3-phenyl moiety (B-ring). Methoxy substitution contributed to inhibition at positions 3 and 5, but had a negative effect at position 4. Finally, methoxy groups at positions 3, 4, and 5 of the B-ring markedly increased cytotoxicity and, therefore, should be avoided.
- Valdameri, Glaucio,Gauthier, Charlotte,Terreux, Rapha?l,Kachadourian, Rémy,Day, Brian J.,Winnischofer, Sheila M. B.,Rocha, Maria E. M.,Frachet, Véronique,Ronot, Xavier,Di Pietro, Attilio,Boumendjel, Ahcène
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scheme or table
p. 3193 - 3200
(2012/06/01)
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- Synthesis of a Range of Polyhydroxy 8-Aryl Flavones
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The 8-iodo flavones formed by cyclization of benzyl-protected chalcones with iodine in dimethyl sulfoxide have been transformed by a Suzuki coupling reaction into a variety of 8-aryl derivatives. Deprotection with boron tribromide has generated a family of new 8-aryl flavones containing four to eight hydroxyl groups.
- Larsen, Lesley,Yoon, Dong Hee,Weavers, Rex T.
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experimental part
p. 2935 - 2948
(2009/12/03)
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- Structure - Activity relationship studies of chalcone leading to 3-hydroxy-4,3′,4′,5′-tetramethoxychalcone and its analogues as potent nuclear factor κB inhibitors and their anticancer activities
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Chalcone is a privileged structure, demonstrating promising anti-inflammatory and anticancer activities. One potential mechanism is to suppress nuclear factor kappa B (NF-κB) activation. The structures of chalcone-based NF-κB inhibitors vary significantly that there is minimum information about their structure-activity relationships (SAR). This study aims to establish SAR of chalcone-based compounds to NF-κB inhibition, to explore the feasibility of developing simple chalcone-based potent NF-κB inhibitors, and to evaluate their anticancer activities. Three series of chalcones were synthesized in one to three steps with the key step being aldol condensation. These candidates demonstrated a wide range of NF-κB inhibitory activities, some of low micromolar potency, establishing that structural complexity is not required for NF-κB inhibition. Lead compounds also demonstrate potent cytotoxicity against lung cancer cells. Their cytotoxicities correlate moderately well with their NF-κB inhibitory activities, suggesting that suppressing NF-κB activation is likely responsible for at least some of the cytotoxicities. One lead compound effectively inhibits lung tumor growth with no signs of adverse side effects.
- Srinivasan, Balasubramanian,Johnson, Thomas E.,Lad, Rahul,Xing, Chengguo
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experimental part
p. 7228 - 7235
(2010/08/19)
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- Antimitotic and antiproliferative activities of chalcones: Forward structure-activity relationship
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A series of 59 chalcones was prepared and evaluated for the antimitotic effect against K562 leukemia cells. The most active chalcones were evaluated for their antiproliferative activity against a panel of 11 human and murine cell cancer lines. We found that three chalcones were of great interest as potential antimitotic drugs. In vivo safety studies conducted on one of the most active chalcones revealed that the compound was safe, allowing further in vivo antitumor evaluation.
- Boumendjel, Ahcène,Boccard, Julien,Carrupt, Pierre-Alain,Nicolle, Edwige,Blanc, Madeleine,Geze, Annabelle,Choisnard, Luc,Wouessidjewe, Denis,Matera, Eva-Laure,Dumontet, Charles
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p. 2307 - 2310
(2008/12/22)
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- Synthesis of chalcone analogues with increased antileishmanial activity
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Eighteen analogues of an active natural chalcone were synthesized using xanthoxyline and some derivatives, and these analogues were tested for selective activity against both promastigotes and intracellular amastigotes of Leishmania amazonensis in vitro. Three analogues (10, 12, and 19) containing nitro, fluorine or bromine groups, respectively, displayed increased selective activity against the parasites as compared with the natural chalcone. The nitrosylated chalcone 10 was also tested intralesionally in infected mice and was found to be as effective as Pentostan reference drug at a dose 100 times higher than that of the chalcone in controlling both the lesion growth and the parasite burden.
- Boeck, Paula,Bandeira Falcao, Camila Alves,Leal, Paulo Cesar,Yunes, Rosendo Augusto,Filho, Valdir Cechinel,Torres-Santos, Eduardo Caio,Rossi-Bergmann, Bartira
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p. 1538 - 1545
(2007/10/03)
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- Synthesis of isoflavones containing naturally occurring substitution pattern by oxidative rearrangement of respective flavanones using thallium(III) p-tosylate
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Claisen condensation of substituted 2′-hydroxyacetophenones 1a-c with aromatic aldehydes affords respective substituted 2′-hydroxychalcones 2a-n which on base catalyzed cyclization in pyridine:methanol:water (1:1:1) give respective flavanones 3a-n. The oxidative rearrangement of flavanones with thallium(III) p-tosylate furnishes respective isoflavones 4a-n in overall 62-72% yields starting from 1. The present methodology has been successfully applied for the synthesis of naturally occurring isoflavones such as di-O-methyldaidzein 4a, cabruvin 4b, pseudobabtigenin methylether 4d, 5,7-dimethoxyisoflavone 4f, 5,7,4′-trimethoxyisoflavone 4g, derrustone 4i, 7,8,3′,4′- tetramethoxyisoflavone 41, purpuranin-A 4m and 7,8,3′,4′,5′- pentamethoxyisoflavone 4n and thus the first synthesis of 4n is reported.
- Singh, Om V.,Muthukrishnan,Sunderavadivelu
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p. 2575 - 2581
(2007/10/03)
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- Flavonoids: Structural requirements for antiproliferative activity on breast cancer cells
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Several classes of flavonoids (flavones, flavanones, 2′-hydroxychalcones and flavan-4-ols) having a variety of substituents on A ring were investigated for their antiproliferative activity against MCF-7 human breast cancer cells. Structure-activity relationships of these compounds were discussed. 2′-hydroxychalcones and methoxylated flavanones were found to be potent inhibitors of MCF-7 cells growth whereas flavones and flavan-4-ols appeared to be weak inhibitory agents except 7,8-dihydroxyflavone.
- Pouget, Christelle,Lauthier, Fabienne,Simon, Alain,Fagnere, Catherine,Basly, Jean-Philippe,Delage, Christiane,Chulia, Albert-Jose
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p. 3095 - 3097
(2007/10/03)
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- Antispasmodic activity of xanthoxyline derivatives: Structure-activity relationships
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The antispasmodic activity of several xanthoxyline derivatives against acetylcholine-induced contraction of the guinea pig ileum was evaluated in vitro. The acetophenones with two methoxyl groups, mainly in the 3,4 positions, exhibited potent antispasmodic activity. Modification of the hydroxyl group in xanthoxyline by the introduction of benzoyl, acetyl, or tosyl groups produced inactive compounds, whereas the introduction of benzyl or p-methoxybenzyl groups furnished compounds that were four- to eight-fold more potent than xanthoxyline. In marked contrast, the introduction of a methyl group gave a compound that caused contractant activity. Modification of the carbonyl group of xanthoxyline lead to inactive compounds, whereas the condensation of xanthoxyline with benzaldehydes gave chalkones that were about fivefold more potent than xanthoxyline. The introduction of benzyl and styrene groups, on the basis of the similarity with papaverine, improves the antispasmodic action of the xanthoxyline derivatives. Our results suggest that the methoxyl and carbonyl groups are critical structural points for the antispasmodic activity of xanthoxyline derivatives. The hydroxyl group improves antispasmodic activity, but is not fundamental to its manifestation.
- Filho,Miguel,Nunes,Calixto,Yunes
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p. 473 - 475
(2007/10/02)
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- 13C Nuclear Magnetic Resonance Studies on 1,3-Diphenylprop-2-enones
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The 13C NMR spectra of 48 differently substituted chalcones (1,3-diphenylprop-2-enones) have been recorded and the results are discussed.The data will be useful in the identification of new/natural chalcones.
- Parmar, V. S.,Sharma, Sunil,Rathore, J. S.,Garg, Meenu,Gupta, Sandhya,et al.
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p. 470 - 474
(2007/10/02)
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- Synthesis of 2-Benzylidene-3(2H)-benzofuran-3-ones (Aurones) by Oxidation of 2'-Hydroxychalcones with Mercury(II) Acetate
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The reaction of 2'-hydroxychalcones with mercury(II) acetate in acetic acid gives predominantly 2-benzylidene-3(2H)-benzofuran-3-ones (aurones) in 28-62 percent yield accompanied by flavonones in 5-21 percent yield.
- Sekizaki, Haruo
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p. 1407 - 1409
(2007/10/02)
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- Substituted acetophenones and compositions containing them
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Antivirally active compounds of the formula STR1 wherein R1 represents hydroxy, acyloxy derived from an aliphatic acid having 2-18 carbon atoms or a heterocyclic carboxylic acid containing nitrogen atom(s), lower alkoxycarbonyloxy, aminoacyloxy or carboxyalkanoyloxy; R2 represents lower alkoxy; R3 represents hydrogen or lower alkoxy; and R4 represents phenyl which may be substituted by one or more substituents selected from the group consisting of lower alkyl, lower alkoxy, benzyloxy, allyloxy, alkylthio, dialkylamino, amino, cyano, hydroxy, halo and alkylenedioxy; or pyridyl, furyl, thienyl or pyrrolyl which may be substituted by lower alkyl, pharmaceutical compositions containing them and a process for the preparation of those compounds of formula I which are novel.
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- Dye-sensitized Photo-oxygenation of Chalcones
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The dye-sensitized photo-oxygenation of several chalcones has been examined.Some of the chalcones give rise to degradation products while others lead to flavonol formation.A rational explanation for the observations has been proposed.The study may have a significance in the biogenesis of naturally occurring plant polyphenolics.
- Chawla, H. Mohindra,Chakrabarty, Kakoli
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p. 1511 - 1513
(2007/10/02)
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