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Molecules, Volume 21, Issue 10 (October 2016)

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Cover Story (view full-size image) During recent decades, numerous studies were performed to evaluate the neuroprotective effects of [...] Read more.
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Open AccessCorrection Correction: Chae, H.S.; et al. Atractylodin Inhibits Interleukin-6 by Blocking NPM-ALK Activation and MAPKs in HMC-1. Molecules 2016, 21, 1169
Molecules 2016, 21(10), 1412; https://doi.org/10.3390/molecules21101412
Received: 12 October 2016 / Accepted: 19 October 2016 / Published: 25 October 2016
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Abstract
The authors wish to make the following correction to their paper [1].[...] Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Chemical Constituents from the Aerial Parts of Cyrtopodium paniculatum
Molecules 2016, 21(10), 1418; https://doi.org/10.3390/molecules21101418
Received: 17 September 2016 / Revised: 9 October 2016 / Accepted: 19 October 2016 / Published: 24 October 2016
Cited by 3 | PDF Full-text (1189 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
We report the first phytochemical study of the neotropical orchid Cyrtopodium paniculatum. Eight new compounds, including one phenanthrene 1, one 9,10-dihydro-phenanthrene 2, one hydroxybenzylphenanthrene 3, two biphenanthrenes 45, and three 9,10 dihydrophenanthrofurans 68,
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We report the first phytochemical study of the neotropical orchid Cyrtopodium paniculatum. Eight new compounds, including one phenanthrene 1, one 9,10-dihydro-phenanthrene 2, one hydroxybenzylphenanthrene 3, two biphenanthrenes 45, and three 9,10 dihydrophenanthrofurans 68, together with 28 known phenolic compounds, mostly stilbenoids, were isolated from the CH2Cl2 extract of its leaves and pseudobulbs. The structures of the new compounds were established on the basis of extensive spectroscopic methods. Full article
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Open AccessArticle Exogenous Methyl Jasmonate and Salicylic Acid Induce Subspecies-Specific Patterns of Glucosinolate Accumulation and Gene Expression in Brassica oleracea L.
Molecules 2016, 21(10), 1417; https://doi.org/10.3390/molecules21101417
Received: 16 September 2016 / Revised: 18 October 2016 / Accepted: 19 October 2016 / Published: 24 October 2016
Cited by 6 | PDF Full-text (2653 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Glucosinolates have anti-carcinogenic properties. In the recent decades, the genetics of glucosinolate biosynthesis has been widely studied, however, the expression of specific genes involved in glucosinolate biosynthesis under exogenous phytohormone treatment has not been explored at the subspecies level in Brassica oleracea.
[...] Read more.
Glucosinolates have anti-carcinogenic properties. In the recent decades, the genetics of glucosinolate biosynthesis has been widely studied, however, the expression of specific genes involved in glucosinolate biosynthesis under exogenous phytohormone treatment has not been explored at the subspecies level in Brassica oleracea. Such data are vital for strategies aimed at selective exploitation of glucosinolate profiles. This study quantified the expression of 38 glucosinolate biosynthesis-related genes in three B. oleracea subspecies, namely cabbage, broccoli and kale, and catalogued associations between gene expression and increased contents of individual glucosinolates under methyl jasmonate (MeJA) and salicylic acid (SA) treatments. Glucosinolate accumulation and gene expression in response to phytohormone elicitation was subspecies specific. For instance, cabbage leaves showed enhanced accumulation of the aliphatic glucoiberin, progoitrin, sinigrin and indolic neoglucobrassicin under both MeJA and SA treatment. MeJA treatment induced strikingly higher accumulation of glucobrassicin (GBS) in cabbage and kale and of neoglucobrassicin (NGBS) in broccoli compared to controls. Notably higher expression of ST5a (Bol026200), CYP81F1 (Bol028913, Bol028914) and CYP81F4 genes was associated with significantly higher GBS accumulation under MeJA treatment compared to controls in all three subspecies. CYP81F4 genes, trans-activated by MYB34 genes, were expressed at remarkably high levels in all three subspecies under MeJA treatment, which also induced in higher indolic NGBS accumulation in all three subspecies. Remarkably higher expression of MYB28 (Bol036286), ST5b, ST5c, AOP2, FMOGS-OX5 (Bol031350) and GSL-OH (Bol033373) was associated with much higher contents of aliphatic glucosinolates in kale leaves compared to the other two subspecies. The genes expressed highly could be utilized in strategies to selectively increase glucosinolate compounds in B. oleracea subspecies. These results promote efforts to develop genotypes of B. oleracea and other species with enhanced levels of desired glucosinolates. Full article
(This article belongs to the Section Molecular Diversity)
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Open AccessCorrection Correction: Chae, H.S., et al. Anti-Inflammatory Effects of 6,8-Diprenyl-7,4′-dihydroxyflavanone from Sophora tonkinensis on Lipopolysaccharide-Stimulated RAW 264.7 Cells. Molecules. 2016, 21, 1049.
Molecules 2016, 21(10), 1413; https://doi.org/10.3390/molecules21101413
Received: 12 October 2016 / Accepted: 19 October 2016 / Published: 24 October 2016
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Open AccessCommunication Original Synthesis of Fluorenyl Alcohol Derivatives by Reductive Dehalogenation Initiated by TDAE
Molecules 2016, 21(10), 1408; https://doi.org/10.3390/molecules21101408
Received: 19 September 2016 / Revised: 18 October 2016 / Accepted: 19 October 2016 / Published: 24 October 2016
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Abstract
We report here a novel and easy-to-handle reductive dehalogenation of 9-bromofluorene in the presence of arylaldehydes and dicarbonyl derivatives to give the corresponding fluorenyl alcohol derivatives and Darzens epoxides as by-products in tetrakis(dimethylamino)ethylene (TDAE) reaction conditions. The reaction is believed to proceed via
[...] Read more.
We report here a novel and easy-to-handle reductive dehalogenation of 9-bromofluorene in the presence of arylaldehydes and dicarbonyl derivatives to give the corresponding fluorenyl alcohol derivatives and Darzens epoxides as by-products in tetrakis(dimethylamino)ethylene (TDAE) reaction conditions. The reaction is believed to proceed via two successive single electron transfers to generate the fluorenyl anion which was able to react with different electrophiles. A mechanistic study was conducted to understand the formation of the epoxide derivatives. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle Naturally Occurring Cinnamic Acid Sugar Ester Derivatives
Molecules 2016, 21(10), 1402; https://doi.org/10.3390/molecules21101402
Received: 30 September 2016 / Revised: 30 September 2016 / Accepted: 12 October 2016 / Published: 24 October 2016
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Abstract
Cinnamic acid sugar ester derivatives (CASEDs) are a class of natural product with one or several phenylacrylic moieties linked with the non-anomeric carbon of a glycosyl skeleton part through ester bonds. Their notable anti-depressant and brains protective activities have made them a topic
[...] Read more.
Cinnamic acid sugar ester derivatives (CASEDs) are a class of natural product with one or several phenylacrylic moieties linked with the non-anomeric carbon of a glycosyl skeleton part through ester bonds. Their notable anti-depressant and brains protective activities have made them a topic of great interest over the past several decades. In particular the compound 3′,6-disinapoylsucrose, the index component of Yuanzhi (a well-known Traditional Chinese Medicine or TCM), presents antidepressant effects at a molecular level, and has become a hotspot of research on new lead drug compounds. Several other similar cinnamic acid sugar ester derivatives are reported in traditional medicine as compounds to calm the nerves and display anti-depression and neuroprotective activity. Interestingly, more than one third of CASEDs are distributed in the family Polygalaceae. This overview discusses the isolation of cinnamic acid sugar ester derivatives from plants, together with a systematic discussion of their distribution, chemical structures and properties and pharmacological activities, with the hope of providing references for natural product researchers and draw attention to these interesting compounds. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessReview Development and Applications of the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) as a Bioorthogonal Reaction
Molecules 2016, 21(10), 1393; https://doi.org/10.3390/molecules21101393
Received: 29 September 2016 / Revised: 14 October 2016 / Accepted: 15 October 2016 / Published: 24 October 2016
Cited by 16 | PDF Full-text (3330 KB) | HTML Full-text | XML Full-text
Abstract
The emergence of bioorthogonal reactions has greatly broadened the scope of biomolecule labeling and detecting. Of all the bioorthogonal reactions that have been developed, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) is the most widely applied one, mainly because of its relatively fast kinetics and
[...] Read more.
The emergence of bioorthogonal reactions has greatly broadened the scope of biomolecule labeling and detecting. Of all the bioorthogonal reactions that have been developed, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) is the most widely applied one, mainly because of its relatively fast kinetics and high efficiency. However, the introduction of copper species to in vivo systems raises the issue of potential toxicity. In order to reduce the copper-induced toxicity and further improve the reaction kinetics and efficiency, different strategies have been adopted, including the development of diverse copper chelating ligands to assist the catalytic cycle and the development of chelating azides as reagents. Up to now, the optimization of CuAAC has facilitated its applications in labeling and identifying either specific biomolecule species or on the omics level. Herein, we mainly discuss the efforts in the development of CuAAC to better fit the bioorthogonal reaction criteria and its bioorthogonal applications both in vivo and in vitro. Full article
(This article belongs to the Special Issue Recent Advances in CuAAC Click Chemistry)
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Open AccessArticle Isobutylhydroxyamides from Zanthoxylum bungeanum and Their Suppression of NO Production
Molecules 2016, 21(10), 1416; https://doi.org/10.3390/molecules21101416
Received: 18 September 2016 / Revised: 8 October 2016 / Accepted: 10 October 2016 / Published: 23 October 2016
Cited by 5 | PDF Full-text (628 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Four new unsaturated aliphatic acid amides, named zanthoamides A–D (14), and eight known ones—tetrahydrobungeanool (5), ZP-amide A (6), ZP-amide B (7), ZP-amide C (8), ZP-amide D (9), ZP-amide E
[...] Read more.
Four new unsaturated aliphatic acid amides, named zanthoamides A–D (14), and eight known ones—tetrahydrobungeanool (5), ZP-amide A (6), ZP-amide B (7), ZP-amide C (8), ZP-amide D (9), ZP-amide E (10), bugeanumamide A (11), and (2E,7E,9E)-N-(2-hydroxy-2-methylpropyl)-6,11-dioxo-2,7,9-dodecatrienamide (12)—were isolated from the pericarps of Zanthoxylum bungeanum. The structures of these compounds were elucidated by extensive use of spectroscopic methods, including HRESIMS, 1D and 2D NMR analyses and comparison with previously reported data. Compound 4 contained a rare C6 fatty acid unit with an acetal group. Results revealed that compounds 1, 5, 6, and 12 showed inhibitory effects on nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages, with IC50values of 48.7 ± 0.32, 27.1 ± 1.15, 49.8 ± 0.38, and 39.4 ± 0.63 µM, respectively, while the other compounds were inactive (IC50 > 60 μM). They could contribute to the anti-inflammatory effects of Z. bungeanum by suppression of NO production. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessArticle Design, Synthesis and Biological Evaluation of 6-(2,6-Dichloro-3,5-dimethoxyphenyl)-4-substituted-1H-indazoles as Potent Fibroblast Growth Factor Receptor Inhibitors
Molecules 2016, 21(10), 1407; https://doi.org/10.3390/molecules21101407
Received: 10 September 2016 / Revised: 13 October 2016 / Accepted: 17 October 2016 / Published: 23 October 2016
Cited by 3 | PDF Full-text (3971 KB) | HTML Full-text | XML Full-text
Abstract
Tyrosine kinase fibroblast growth factor receptor (FGFR), which is aberrant in various cancer types, is a promising target for cancer therapy. Here we reported the design, synthesis, and biological evaluation of a new series of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-4-substituted-1H-indazole derivatives as potent FGFR inhibitors.
[...] Read more.
Tyrosine kinase fibroblast growth factor receptor (FGFR), which is aberrant in various cancer types, is a promising target for cancer therapy. Here we reported the design, synthesis, and biological evaluation of a new series of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-4-substituted-1H-indazole derivatives as potent FGFR inhibitors. The compound 6-(2,6-dichloro-3,5-dimethoxyphenyl)-N-phenyl-1H-indazole-4-carboxamide (10a) was identified as a potent FGFR1 inhibitor, with good enzymatic inhibition. Further structure-based optimization revealed that 6-(2,6-dichloro-3,5-dimethoxyphenyl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-indazole-4-carboxamide (13a) is the most potent FGFR1 inhibitor in this series, with an enzyme inhibitory activity IC50 value of about 30.2 nM. Full article
(This article belongs to the Special Issue Kinase Inhibitor Chemistry)
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Open AccessArticle Laurus nobilis, Zingiber officinale and Anethum graveolens Essential Oils: Composition, Antioxidant and Antibacterial Activities against Bacteria Isolated from Fish and Shellfish
Molecules 2016, 21(10), 1414; https://doi.org/10.3390/molecules21101414
Received: 25 July 2016 / Revised: 7 October 2016 / Accepted: 17 October 2016 / Published: 22 October 2016
Cited by 6 | PDF Full-text (703 KB) | HTML Full-text | XML Full-text
Abstract
Several bacterial strains were isolated from wild and reared fish and shellfish. The identification of these strains showed the dominance of the Aeromonas hydrophila species in all seafood samples, followed by Staphylococcus spp., Vibrio alginolyticus, Enterobacter cloacae, Klebsiella ornithinolytica, Klebsiella
[...] Read more.
Several bacterial strains were isolated from wild and reared fish and shellfish. The identification of these strains showed the dominance of the Aeromonas hydrophila species in all seafood samples, followed by Staphylococcus spp., Vibrio alginolyticus, Enterobacter cloacae, Klebsiella ornithinolytica, Klebsiella oxytoca and Serratia odorifera. The isolates were studied for their ability to produce exoenzymes and biofilms. The chemical composition of the essential oils from Laurus nobilis leaves, Zingiber officinale rhizomes and Anethum graveolens aerial parts was studied by GC and GC/MS. The essential oils’ antioxidant and antibacterial activities against the isolated microorganisms were studied. Low concentrations of the three essential oils were needed to inhibit the growth of the selected bacteria and the lowest MBCs values were obtained for the laurel essential oil. The selected essential oils can be used as a good natural preservative in fish food due to their antioxidant and antibacterial activities. Full article
(This article belongs to the collection Recent Advances in Flavors and Fragrances)
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Open AccessArticle Potential Anticancer Effects of Polyphenols from Chestnut Shell Extracts: Modulation of Cell Growth, and Cytokinomic and Metabolomic Profiles
Molecules 2016, 21(10), 1411; https://doi.org/10.3390/molecules21101411
Received: 20 September 2016 / Revised: 18 October 2016 / Accepted: 18 October 2016 / Published: 21 October 2016
Cited by 3 | PDF Full-text (1519 KB) | HTML Full-text | XML Full-text
Abstract
In this study, a hydroalcoholic chestnut shell extract was characterized and tested on six different human cell lines. Gallic, ellagic, and syringic acids were the most abundant non-condensed compounds in the chestnut extract, as determined by high performance liquid chromatography (HPLC). Tannins were
[...] Read more.
In this study, a hydroalcoholic chestnut shell extract was characterized and tested on six different human cell lines. Gallic, ellagic, and syringic acids were the most abundant non-condensed compounds in the chestnut extract, as determined by high performance liquid chromatography (HPLC). Tannins were mainly represented by condensed monomeric units of epigallocatechin and catechin/epicatechin. After 48 h of treatment, only the human hepatoblastoma HepG2 cells reached an inhibition corresponding to IC50 with an increase of apoptosis and mitochondrial depolarization. The cytokinome evaluation before and after treatment revealed that the vascular endothelial growth factor (VEGF) and the tumor necrosis factor (TNF)-α decreased after the treatment, suggesting a potential anti-angiogenic and anti-inflammatory effect of this extract. Moreover, the metabolome evaluation by 1H-NMR evidenced that the polyphenols extracted from chestnut shell (PECS) treatment affected the levels of some amino acids and other metabolites. Overall, these data highlight the effects of biomolecules on cell proliferation, apoptosis, cell cycle and mitochondrial depolarization, and on cytokinomics and metabolomics profiles. Full article
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Open AccessArticle A Fast and Robust UHPLC-MRM-MS Method to Characterize and Quantify Grape Skin Tannins after Chemical Depolymerization
Molecules 2016, 21(10), 1409; https://doi.org/10.3390/molecules21101409
Received: 30 September 2016 / Revised: 18 October 2016 / Accepted: 19 October 2016 / Published: 21 October 2016
Cited by 5 | PDF Full-text (2288 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A rapid, sensitive, and selective analysis method using ultra high performance liquid chromatography coupled with triple-quadrupole mass spectrometry (UHPLC-QqQ-MS) has been developed for the characterization and quantification of grape skin flavan-3-ols after acid-catalysed depolymerization in the presence of phloroglucinol (phloroglucinolysis). The compound detection
[...] Read more.
A rapid, sensitive, and selective analysis method using ultra high performance liquid chromatography coupled with triple-quadrupole mass spectrometry (UHPLC-QqQ-MS) has been developed for the characterization and quantification of grape skin flavan-3-ols after acid-catalysed depolymerization in the presence of phloroglucinol (phloroglucinolysis). The compound detection being based on specific MS transitions in Multiple Reaction Monitoring (MRM) mode, this fast gradient robust method allows analysis of constitutive units of grape skin proanthocyanidins, including some present in trace amounts, in a single injection, with a throughput of 6 samples per hour. This method was applied to a set of 214 grape skin samples from 107 different red and white grape cultivars grown under two conditions in the vineyard, irrigated or non-irrigated. The results of triplicate analyses confirmed the robustness of the method, which was thus proven to be suitable for high-throughput and large-scale metabolomics studies. Moreover, these preliminary results suggest that analysis of tannin composition is relevant to investigate the genetic bases of grape response to drought. Full article
(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues)
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Open AccessArticle Capsaicin Suppresses Cell Proliferation, Induces Cell Cycle Arrest and ROS Production in Bladder Cancer Cells through FOXO3a-Mediated Pathways
Molecules 2016, 21(10), 1406; https://doi.org/10.3390/molecules21101406
Received: 7 September 2016 / Revised: 13 October 2016 / Accepted: 18 October 2016 / Published: 21 October 2016
Cited by 6 | PDF Full-text (6916 KB) | HTML Full-text | XML Full-text
Abstract
Capsaicin (CAP), a highly selective agonist for transient receptor potential vanilloid type 1 (TRPV1), has been widely reported to exhibit anti-oxidant, anti-inflammation and anticancer activities. Currently, several therapeutic approaches for bladder cancer (BCa) are available, but accompanied by unfavorable outcomes. Previous studies reported
[...] Read more.
Capsaicin (CAP), a highly selective agonist for transient receptor potential vanilloid type 1 (TRPV1), has been widely reported to exhibit anti-oxidant, anti-inflammation and anticancer activities. Currently, several therapeutic approaches for bladder cancer (BCa) are available, but accompanied by unfavorable outcomes. Previous studies reported a potential clinical effect of CAP to prevent BCa tumorigenesis. However, its underlying molecular mechanism still remains unknown. Our transcriptome analysis suggested a close link among calcium signaling pathway, cell cycle regulation, ROS metabolism and FOXO signaling pathway in BCa. In this study, several experiments were performed to investigate the effects of CAP on BCa cells (5637 and T24) and NOD/SCID mice. Our results showed that CAP could suppress BCa tumorigenesis by inhibiting its proliferation both in vitro and in vivo. Moreover, CAP induced cell cycle arrest at G0/G1 phase and ROS production. Importantly, our studies revealed a strong increase of FOXO3a after treatment with CAP. Furthermore, we observed no significant alteration of apoptosis by CAP, whereas Catalase and SOD2 were considerably upregulated, which could clear ROS and protect against cell death. Thus, our results suggested that CAP could inhibit viability and tumorigenesis of BCa possibly via FOXO3a-mediated pathways. Full article
(This article belongs to the Special Issue Capsaicin)
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Open AccessArticle The Inhibition Effect of Cell DNA Oxidative Damage and LDL Oxidation by Bovine Colostrums
Molecules 2016, 21(10), 1378; https://doi.org/10.3390/molecules21101378
Received: 11 August 2016 / Revised: 4 October 2016 / Accepted: 19 October 2016 / Published: 21 October 2016
Cited by 1 | PDF Full-text (1789 KB) | HTML Full-text | XML Full-text
Abstract
In the present study, we investigated the effect of bovine colostrums on inhibition of DNA oxidative damage and low density lipoprotein (LDL) oxidation in vitro. Results showed that whey and skimmed milk exhibited not only higher inhibitory activities of oxidative damage of deoxyribose
[...] Read more.
In the present study, we investigated the effect of bovine colostrums on inhibition of DNA oxidative damage and low density lipoprotein (LDL) oxidation in vitro. Results showed that whey and skimmed milk exhibited not only higher inhibitory activities of oxidative damage of deoxyribose but also an inhibitory effect on the breakdown of supercoiled DNA into open circular DNA and linear DNA. The quantities of 8-OH-2′-dG formed under whey, caseins and skimmed milk treatment were 0.24, 0.24 and 1.24 μg/mL, respectively. The quantity of malondialdehyde formed through LDL oxidation induced by copprous ion was significantly decreased as colostrums protein solutions were added, in which whey and caseins led to a more significant decrease than skimmed milk. The formation of conjugated dienes could be inhibited by treatment with colostrums protein solutions. Whey exhibited the longest lag time of conjugated dienes formation among the colostrums proteins. The lag time of the whey was 2.33 times that of the control. From the results of foregoing, the bovine colostrums protein has potential value in the inhibition of DNA oxidation damage and LDL oxidation. Full article
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Open AccessArticle Identification of Novel Human Breast Carcinoma (MDA-MB-231) Cell Growth Modulators from a Carbohydrate-Based Diversity Oriented Synthesis Library
Molecules 2016, 21(10), 1405; https://doi.org/10.3390/molecules21101405
Received: 18 August 2016 / Revised: 12 October 2016 / Accepted: 15 October 2016 / Published: 20 October 2016
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Abstract
The application of a cell-based growth inhibition on a library of skeletally different glycomimetics allowed for the selection of a hexahydro-2H-furo[3,2-b][1,4]oxazine compound as candidate inhibitors of MDA-MB-231 cell growth. Subsequent synthesis of analogue compounds and preliminary biological studies validated
[...] Read more.
The application of a cell-based growth inhibition on a library of skeletally different glycomimetics allowed for the selection of a hexahydro-2H-furo[3,2-b][1,4]oxazine compound as candidate inhibitors of MDA-MB-231 cell growth. Subsequent synthesis of analogue compounds and preliminary biological studies validated the selection of a valuable hit compound with a novel polyhydroxylated structure for the modulation of the breast carcinoma cell cycle mechanism. Full article
(This article belongs to the Special Issue Diversity Oriented Synthesis 2016)
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